From 8e6499fb1e2eda6c2cfb1aab480166a3acadb03a Mon Sep 17 00:00:00 2001 From: Davide Grilli Date: Fri, 9 Oct 2026 14:37:59 +0200 Subject: [PATCH] Rimuove i JSON intermedi di MinerU Non servono a tesi.md; restano recuperabili dalla cronologia (49d26f7). Co-Authored-By: Claude Sonnet 5.5 --- tesi_docx.json | 17385 ------- tesi_pdf.json | 127835 ---------------------------------------------- 2 files changed, 145220 deletions(-) delete mode 100644 tesi_docx.json delete mode 100644 tesi_pdf.json diff --git a/tesi_docx.json b/tesi_docx.json deleted file mode 100644 index d77c159..0000000 --- a/tesi_docx.json +++ /dev/null @@ -1,17385 +0,0 @@ -{ - "pdf_info": [ - { - "para_blocks": [ - { - "type": "table", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "table", - "html": "

Dipartimento di Chimica Industriale “Toso Montanari”

Corso di Laurea Magistrale in

Chimica Industriale

Classe LM-71 - Scienze e Tecnologie della Chimica Industriale

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CANDIDATO

Aurora Luzi

RELATORE

Dr. Stefano Scurti

CORRELATORE

Prof. Massimiliano Lanzi

Dr. Simone Gabellini

Dr. Riccardo Medri

" - } - ] - } - ], - "index": 4, - "type": "table_body" - } - ], - "index": 4 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "_________________________________________________________________________________________________________________", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 5 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Anno Accademico 2025-2026", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 6 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Riassunto", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 7 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il presente lavoro di tesi si concentra sulla progettazione, sintesi e caratterizzazione di nuove architetture macromolecolari potenzialmente semiconduttrici ed emissive a spazzola, note come copolimeri bottle brush. L'obiettivo principale è superare il fenomeno dello spegnimento dell'emissione indotto dall'aggregazione (Aggregation-Caused Quenching, ACQ), una criticità tipica dei materiali π-coniugati impiegati nel campo della soft optoelectronics. La naturale tendenza di questi sistemi planari a formare forti interazioni intermolecolari di π-stacking causa, infatti, una drastica dissipazione non radiativa dell'energia allo stato solido." - } - ] - } - ], - "index": 8 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Per risolvere questo problema, la strategia sintetica si è basata sulla realizzazione di un monomero ortogonale e multifunzionale derivato dal dichetopirrolopirrolo (DPP). Questo monomero è stato funzionalizzato con anelli tiofenici, che forniscono i siti reattivi per l'accrescimento della catena principale, e con gruppi ossidrilici terminali, che fungono da iniziatori indipendenti per l'innesto delle catene laterali. Successivamente, mediante polimerizzazione ossidativa diretta con 3-esiltiofene (3HT), è stato creato lo scheletro polimerico coniugato. L'architettura bottle brush finale è stata realizzata tramite polimerizzazione ad apertura d'anello (ROP) dell'ε-caprolattone, facendo crescere catene laterali flessibili di policaprolattone (PCL) con diversi pesi molecolari (1500, 5000 e 10000 Da)." - } - ] - } - ], - "index": 9 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le analisi spettroscopiche (1H-NMR e FT-IR) e cromatografiche (GPC) hanno confermato il successo della sintesi e l'ottenimento di macromolecole ramificate ad alta densità strutturale. La caratterizzazione ottica ha dimostrato che, mentre in soluzione il core di DPP mantiene intatta la sua integrità elettronica, allo stato solido l'introduzione delle catene laterali di PCL agisce efficacemente come spaziatore sterico. Questo ingombro limita l'eccessivo impaccamento intermolecolare, permettendo al materiale di conservare un'apprezzabile emissione nel rosso e attenuando così i percorsi di disattivazione non radiativa tipici dell'ACQ." - } - ] - } - ], - "index": 10 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Infine, le indagini elettrochimiche condotte tramite ciclovoltammetria hanno introdotto lo studio delle proprietà semiconduttrici dei materiali sintetizzati. I risultati hanno evidenziato una netta correlazione lineare tra la percentuale di DPP incorporata nello scheletro e l'allargamento del bandgap elettrochimico." - } - ] - } - ], - "index": 11 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In conclusione, il design macromolecolare proposto si è rivelato un approccio altamente efficace per combinare proprietà elettrochimiche modulabili e capacità emissive allo stato solido, confermandone il potenziale per future applicazioni in dispositivi optoelettronici." - } - ] - } - ], - "index": 12 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Abstract", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 13, - "is_numbered_style": false, - "level": 2 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "This thesis focuses on the design, synthesis, and characterization of novel semiconducting and emissive brush-like macromolecular architectures, known as bottle brush copolymers. The main objective is to overcome the phenomenon of Aggregation-Caused Quenching (ACQ), a typical critical issue of π-conjugated materials used in the field of soft optoelectronics. The natural tendency of these planar systems to form strong intermolecular π-stacking interactions causes, in fact, a drastic non-radiative energy dissipation in the solid state." - } - ] - } - ], - "index": 14 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "To solve this problem, the synthetic strategy was based on the creation of an orthogonal and multifunctional monomer derived from diketopyrrolopyrrole (DPP). This monomer was functionalized with thiophene rings, which provide the reactive sites for the growth of the main chain, and with terminal hydroxyl groups, which act as independent initiators for the grafting of the side chains. Subsequently, the conjugated polymeric backbone was created through direct oxidative polymerization with 3-hexylthiophene (3HT). The final bottle brush architecture was achieved via ring-opening polymerization (ROP) of ε-caprolactone, growing flexible side chains of polycaprolactone (PCL) with different molecular weights (1500, 5000, and 10000 Da)." - } - ] - } - ], - "index": 15 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Spectroscopic (1H-NMR and FT-IR) and chromatographic (GPC) analyses confirmed the success of the synthesis and the obtainment of branched macromolecules with high structural density. Optical characterization demonstrated that, while in solution the DPP core keeps its electronic integrity intact, in the solid state the introduction of the PCL side chains acts effectively as a steric spacer. This steric hindrance limits the excessive intermolecular packing, allowing the material to retain an appreciable emission in the red and thus attenuating the non-radiative deactivation pathways typical of ACQ." - } - ] - } - ], - "index": 16 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Finally, electrochemical investigations conducted via cyclic voltammetry were performed to assess the semiconducting properties of the synthesized materials. The results highlighted a clear linear correlation between the percentage of DPP incorporated into the backbone and the widening of the electrochemical bandgap. In conclusion, the proposed macromolecular design proved to be a highly effective approach for combining tunable electrochemical properties and solid-state emissive capabilities, confirming its potential for future applications in optoelectronic devices." - } - ] - } - ], - "index": 17 - }, - { - "type": "index", - "ilevel": 0, - "blocks": [ - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Sommario", - "style": [ - "bold" - ] - } - ] - } - ] - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "1.\tIntroduzione" - } - ] - } - ], - "anchor": "_Toc242438062" - }, - { - "type": "index", - "ilevel": 1, - "blocks": [ - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "1.1.\tDichetopirrolopirroli" - } - ] - } - ], - "anchor": "_Toc242438063" - }, - { - "type": "index", - "ilevel": 2, - "blocks": [ - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "1.1.1.\tStoria e sintesi" - } - ] - } - ], - "anchor": "_Toc242438064" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "1.1.2.\tStruttura e reattività" - } - ] - } - ], - "anchor": "_Toc242438065" - } - ] - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "1.2.\tFluorescenza" - } - ] - } - ], - "anchor": "_Toc242438066" - }, - { - "type": "index", - "ilevel": 2, - "blocks": [ - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "1.2.1. Shift di Stokes" - } - ] - } - ], - "anchor": "_Toc242438067" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "1.2.2. Resa quantica" - } - ] - } - ], - "anchor": "_Toc242438068" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "1.2.3. Tempi di vita" - } - ] - } - ], - "anchor": "_Toc242438069" - } - ] - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "1.3.\tUtilizzo di fluorofori in materiali polimerici" - } - ] - } - ], - "anchor": "_Toc242438070" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "1.4.\tApplicazioni" - } - ] - } - ], - "anchor": "_Toc242438071" - } - ] - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "2.\tScopo" - } - ] - } - ], - "anchor": "_Toc242438072" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "3.\tProcedure sperimentali" - } - ] - } - ], - "anchor": "_Toc242438073" - }, - { - "type": "index", - "ilevel": 1, - "blocks": [ - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "3.1.\tMateriali e metodi" - } - ] - } - ], - "anchor": "_Toc242438074" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "3.2.\tSintesi e procedure" - } - ] - } - ], - "anchor": "_Toc242438075" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "3.3.\tPrincipi teorici della ciclovoltammetria" - } - ] - } - ], - "anchor": "_Toc242438076" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "3.4.\tProcedure sperimentali delle analisi voltammetriche" - } - ] - } - ], - "anchor": "_Toc242438077" - } - ] - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "4.\tDiscussione dei risultati" - } - ] - } - ], - "anchor": "_Toc242438078" - }, - { - "type": "index", - "ilevel": 1, - "blocks": [ - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "4.1. 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Metodologie di analisi voltammetrica" - } - ] - } - ], - "anchor": "_Toc242438084" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "4.4.3. Proprietà elettrochimiche dei copolimeri lienari" - } - ] - } - ], - "anchor": "_Toc242438085" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "4.4.4. Effetto del design bottle brush" - } - ] - } - ], - "anchor": "_Toc242438086" - } - ] - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "4.5. Caratterizzazione spettroscopica allo stato solido" - } - ] - } - ], - "anchor": "_Toc242438087" - } - ] - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "5.\tConclusioni" - } - ] - } - ], - "anchor": "_Toc242438088" - } - ], - "index": 18 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Introduzione ", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 19, - "anchor": "_Toc242438062", - "is_numbered_style": true, - "level": 1, - "section_number": "1" - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Dichetopirrolopirroli ", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 20, - "anchor": "_Toc242438063", - "is_numbered_style": true, - "level": 2, - "section_number": "1.1" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I dichetopirrolopirroli (DPP) sono caratterizzati da un nucleo centrale costituito da due anelli lattamici a cinque termini condensati. Tale sistema biciclico presenta due insaturazioni che consentono l’introduzione di opportuni sostituenti aromatici o eteroaromatici periferici, come illustrato in " - }, - { - "type": "text", - "content": "Figura 1", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 21 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 22, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 1", - "style": [ - "bold", - "italic" - ] - }, - { - "type": "text", - "content": " - struttura generica di un dichetopirrolopirrolo", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 23, - "type": "image_caption" - } - ], - "index": 22 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le particolari caratteristiche fisiche di questa molecola, tra cui un punto di fusione molto elevato (>350 °C), la fortissima insolubilità e la tipica colorazione rossa, rimasero inosservate finché i ricercatori della Ciba-Geigy Specialty Chemicals Co. non ne svilupparono i primi derivati, ispirandosi alle analogie strutturali con altri pigmenti già noti" - }, - { - "type": "text", - "content": "1", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 24 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Dal 1986, anno in cui il primo DPP fu immesso sul mercato, sono stati sintetizzati altri coloranti appartenenti a questa famiglia, impiegati con successo nella tintura di materiali plastici, fibre e inchiostri." - } - ] - } - ], - "index": 25 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Con il passare degli anni, l’interesse scientifico verso i DPP si è radicalmente evoluto: da tradizionali pigmenti industriali sono diventate molecole intensamente indagate in svariati settori. La loro architettura, caratterizzata da un’unità planare π-coniugata e dalla presenza di sostituenti ammidici reattivi, permette infatti di modulare finemente le proprietà ottiche ed elettroniche del materiale attraverso specifiche funzionalizzazioni chimiche. È proprio questa versatilità ad averne favorito l’impiego in numerosi campi tecnologici avanzati, come l’optoelettronica, il fotovoltaico" - }, - { - "type": "text", - "content": "2 ", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "e il bio-imaging" - }, - { - "type": "text", - "content": "3,4", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 26 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Storia e sintesi ", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 27, - "anchor": "_Toc242438064", - "is_numbered_style": true, - "level": 3, - "section_number": "1.1.1" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I DPP sono stati scoperti per la prima volta da Farnum et al. nel 1974 quando furono ottenuti come sottoprodotti della sintesi di derivati dell’azetinone mediante una reazione di Reformatskij modificata. I ricercatori hanno mostrato come, facendo reagire bromoacetato e benzonitrile in presenza di zinco, non si ottenga il prodotto desiderato ma un pigmento rosso con una resa del 5-20%. Per confermare la formazione del dichetopirrolopirrolo, Farnum et al. hanno ipotizzato uno schema di reazione riportato in " - }, - { - "type": "text", - "content": "Figura 2", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "." - }, - { - "type": "text", - "content": "2", - "style": [ - "superscript" - ] - } - ] - } - ], - "index": 28 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 29, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 2", - "style": [ - "bold", - "italic" - ] - }, - { - "type": "text", - "content": " - meccanismo di formazione del DPP proposto da Farnum et al", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "2", - "style": [ - "italic", - "superscript" - ] - } - ] - } - ], - "index": 30, - "type": "image_caption" - } - ], - "index": 29 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L’ipotesi prevedeva che il benzonitrile reagisse con l’organozinco, derivante dall’etilbromoacetato, per formare il β-amminocinnamato. Questo intermedio (" - }, - { - "type": "text", - "content": "1", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") in condizioni ossidative genera il dimero (" - }, - { - "type": "text", - "content": "2", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), che per ciclizzazioni consecutive mediante attacco nucleofilo delle due ammine sul carbonile estereo ed eliminazione di due molecole di alcol etilico, porta alla formazione del dichetopirrolopirrolo (" - }, - { - "type": "text", - "content": "3", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 31 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Nel 1988, Iqbal in collaborazione con i ricercatori della Ciba-Geigy Specialty Chemicals Co." - }, - { - "type": "text", - "content": "5", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ", hanno intrapreso studi meccanicistici volti a rendere la produzione di DPP commercialmente sostenibile. Poiché i tentativi basati sull'ipotesi iniziale di Farnum. non avevano portato ai risultati sperati, i ricercatori hanno deciso di approfondire ulteriormente le indagini per chiarire l'effettivo meccanismo di reazione." - } - ] - } - ], - "index": 32 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Inizialmente l’attenzione è stata focalizzata sull’intermedio " - }, - { - "type": "text", - "content": "1", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " per comprenderne l’effettiva partecipazione alla reazione attraverso esperimenti di crossover." - } - ] - } - ], - "index": 33 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Quest’ultimo è stato condotto replicando le condizioni della classica reazione di Reformatskij tra il 4-metilbenzonitrile (" - }, - { - "type": "text", - "content": "A", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), l’etil 2-bromoacetato (" - }, - { - "type": "text", - "content": "B", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") e quantità crescenti di β-amminocinnamato (" - }, - { - "type": "text", - "content": "1", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), sintetizzato separatamente con lo scopo di analizzare la distribuzione dei prodotti in funzione della concentrazione del reagente " - }, - { - "type": "text", - "content": "1 ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "aggiunto (" - }, - { - "type": "text", - "content": "Figura 3", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 34 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 35, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 3 ", - "style": [ - "bold", - "italic" - ] - }, - { - "type": "text", - "content": "- esperimento crossover in presenza di amminocinnamato", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 36, - "type": "image_caption" - } - ], - "index": 35 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Come è possibile osservare in " - }, - { - "type": "text", - "content": "Tabella 1", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", l’aggiunta progressiva di amminocinnamato ha mostrato un conseguente aumento del prodotto " - }, - { - "type": "text", - "content": "4", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", questo conferma la formazione e partecipazione dell’intermedio " - }, - { - "type": "text", - "content": "1", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " alla reazione ed evidenzia la selettività verso il prodotto asimmetrico " - }, - { - "type": "text", - "content": "4", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 37 - }, - { - "type": "table", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tabella 1 ", - "style": [ - "bold", - "italic" - ] - }, - { - "type": "text", - "content": "– descrizione degli esperimenti di crossover e risultati espressi in rapporto molare", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 38, - "type": "table_caption" - }, - { - "lines": [ - { - "spans": [ - { - "type": "table", - "html": "

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" - } - ] - } - ], - "index": 39, - "type": "table_body" - } - ], - "index": 39 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L’indagine meccanicistica si è successivamente concentrata sulla fase di dimerizzazione ossidativa. Nello studio, è stato evidenziato come né l’intermedio " - }, - { - "type": "text", - "content": "1", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", né il suo sale di zinco, diano luogo a dimerizzazione per via termica o in presenza di acidi di Lewis, basi, aria o agenti ossidanti. Al contrario, è stato osservato che ponendo il sale di zinco, visibile in " - }, - { - "type": "text", - "content": "Figura 4 ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "e sintetizzato precedentemente, a reagire con il bromuro B e il benzonitrile, è possibile isolare il DPP " - }, - { - "type": "text", - "content": "3", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 40 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 41, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 4", - "style": [ - "bold", - "italic" - ] - }, - { - "type": "text", - "content": " - sale di zinco derivato dall'intermedio 3", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 42, - "type": "image_caption" - } - ], - "index": 41 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le informazioni ottenute, insieme a quelle fornite precedentemente da Farnum sono state utilizzate per formulare un nuovo meccanismo di reazione, che tenesse conto di tutte le evidenze sperimentali." - } - ] - } - ], - "index": 43 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La sintesi proposta in " - }, - { - "type": "text", - "content": "Figura 5", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " prevede come primo step la condensazione del reagente di Reformatskij con il benzonitrile per produrre il sale di Zn (" - }, - { - "type": "text", - "content": "6", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "). Successivamente si ipotizza una C-alchilazione mediante una seconda molecola di bromoacetato, che porta alla formazione degli intermedi " - }, - { - "type": "text", - "content": "7A", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " e " - }, - { - "type": "text", - "content": "7B ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "in equilibrio tautomerico. Questi reagiscono con il carbonile estereo chiudendo l’anello lattamico a cinque termini e portando alla formazione dell’intermedio " - }, - { - "type": "text", - "content": "8", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ". La condensazione con una seconda molecola di benzonitrile e la successiva ciclizzazione dell’intermedio " - }, - { - "type": "text", - "content": "9", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", isolato e menzionato anche da Farnum, porta alla formazione del DPP " - }, - { - "type": "text", - "content": "3", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ". Con questo penultimo passaggio, inoltre, si spiegherebbe anche l’elevata selettività per il prodotto asimmetrico " - }, - { - "type": "text", - "content": "4", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " menzionato in relazione all’esperimento di crossover." - } - ] - } - ], - "index": 44 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 45, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 5", - "style": [ - "bold", - "italic" - ] - }, - { - "type": "text", - "content": " - meccanismo di formazione del DPP tramite la reazione di Reformtskij", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 46, - "type": "image_caption" - } - ], - "index": 45 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tuttavia, nonostante l'approfondita ricerca condotta sulla base delle precedenti osservazioni, non sono state raggiunte svolte decisive. Sebbene sia stata messa a punto una procedura in grado di garantire rese riproducibili, i loro valori, pari al 25-30% rispetto al bromoacetato e al 60% rispetto a nitrile e zinco, sono risultate insufficienti per decretare la fattibilità commerciale del processo descritto. Sulla base di requisiti essenziali come la disponibilità di materie prime, minimizzazione degli stadi sintetici e fattibilità tecnologica, la ricerca si è orientata verso percorsi alternativi per la sintesi del DPP. Tali strategie sono state sviluppate con l'obiettivo di superare i limiti intrinseci e le criticità operative legati alla metodica di Reformatskij originale." - } - ] - } - ], - "index": 47 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Un’analisi dettagliata del meccanismo riportato in " - }, - { - "type": "text", - "content": "Figura 5", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", supportata da verifiche sperimentali, ha evidenziato come la bassa resa complessiva del DPP " - }, - { - "type": "text", - "content": "3 ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "risulti in netto contrasto con l'elevata efficienza dei singoli passaggi intermedi. In particolare, la formazione del sale di zinco " - }, - { - "type": "text", - "content": "6", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " tramite reazione di Reformatskij procede con rese superiori all’80%, e la ciclizzazione del composto " - }, - { - "type": "text", - "content": "9", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " (precursore immediato del DPP " - }, - { - "type": "text", - "content": "3", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") è risultata pressoché quantitativa. In base alle evidenze riportate in " - }, - { - "type": "text", - "content": "Figura 5", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", è stato quindi dedotto che la C-alchilazione del sale di zinco " - }, - { - "type": "text", - "content": "6", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " rappresenti lo stadio determinante la resa dell'intero processo e che la bassa resa sia dovuta a probabili reazioni collaterali. La reazione in esame porta alla formazione del legame “" - }, - { - "type": "text", - "content": "a", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "”, fondamentale nella molecola di DPP in quanto elemento strutturale condiviso da entrambi gli anelli del sistema biciclico condensato. A seguito di questa ipotesi, il gruppo di ricerca ha provato a sviluppare un processo sintetico che prevedesse l’utilizzo di un reagente che contenesse già al suo interno il legame “" - }, - { - "type": "text", - "content": "a", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "”. Sono stati individuati come possibili candidati degli esteri succinici insieme a nitrili aromatici." - } - ] - } - ], - "index": 48 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 49, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 6 - analisi retrosintetica del DPP proposta da Iqbal et al.", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 50, - "type": "image_caption" - } - ], - "index": 49 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In " - }, - { - "type": "text", - "content": "Figura 6 ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "viene illustrata la strategia retrosintetica della molecola di DPP " - }, - { - "type": "text", - "content": "3 ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "individuata dal gruppo di Iqbal, che forma tre frammenti (" - }, - { - "type": "text", - "content": "X", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", " - }, - { - "type": "text", - "content": "Y", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", " - }, - { - "type": "text", - "content": "X", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") in maniera simmetrica. Tale approccio si basa sul preservare il legame C-C centrale “" - }, - { - "type": "text", - "content": "a” ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "e prevede l’utilizzo di reagenti disponibili in commercio." - } - ] - } - ], - "index": 51 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L’utilizzo della reazione riportata in " - }, - { - "type": "text", - "content": "Figura 7 ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "permette di superare la criticità data dalla formazione del legame C-C centrale, necessaria mediante il metodo Reformatskij, grazie alla preesistenza del legame nell’estere succinico. La reazione descritta, benché non fosse stata riportata in letteratura fino a quel momento, presenta evidenti analogie con la classica condensazione di Stobbe tra un'aldeide (o la corrispondente base di Schiff) ed esteri succinici, processo che conduce alla formazione del sistema dell'ottaidropirrolopirrolo" - }, - { - "type": "text", - "content": "6", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 52 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 53, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 7 - sintesi del DPP proposta da Iqbal et al.", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 54, - "type": "image_caption" - } - ], - "index": 53 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L’efficienza della reazione descritta in " - }, - { - "type": "text", - "content": "Figura 7 ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "dipende strettamente dall'impiego di una base che coniughi un’elevata forza basica ad una ridotta reattività nucleofila, come un alcolato. Queste caratteristiche sono essenziali per favorire la corretta deprotonazione dell’estere succinico e minimizzare le reazioni indesiderate, quali l’attacco nucleofilo al nitrile o la condensazione di Claisen, preservando così l’integrità dei reagenti nel mezzo di reazione. Inoltre, è stato evidenziato come l’aggiunta graduale dell'estere succinico assicuri una bassa concentrazione locale del reagente nel mezzo di reazione, inibendo in questo modo la ciclizzazione competitiva riportata " - }, - { - "type": "text", - "content": "Figura 8", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 55 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 56, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 8", - "style": [ - "bold", - "italic" - ] - }, - { - "type": "text", - "content": " - reazione competitiva di ciclizzazione dell'estere succinico", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 57, - "type": "image_caption" - } - ], - "index": 56 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Allo stesso tempo, è diventato necessario l'impiego di un eccesso di base per compensare la porzione consumata dal DPP; quest'ultimo, data la sua natura relativamente acida, tende infatti a sottrarre base al sistema durante la sintesi" - }, - { - "type": "text", - "content": "5,7", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 58 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Un fattore determinante per limitare la reazione parassita di autocondensazione risiede nella natura chimica del residuo R del diestere. L'incremento dell'ingombro sterico di tale gruppo funge da inibitore per il processo secondario indesiderato. Nello specifico, la resa e la selettività nella sintesi dei dichetopirrolopirroli (DPP) migliorano proporzionalmente alla dimensione del sostituente, seguendo questo preciso ordine di efficacia: " - }, - { - "type": "text", - "content": "t-Am > t-Bu > i-Pr > Et > Me", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 59 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In altre parole, l'impiego di gruppi più voluminosi (come il " - }, - { - "type": "text", - "content": "terz", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "-amile o il " - }, - { - "type": "text", - "content": "terz", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "-butile) permette di ottimizzare la formazione del prodotto principale rispetto a quanto avviene con residui più piccoli come il metile o l'etile." - } - ] - } - ], - "index": 60 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Grazie all'implementazione di queste strategie, il gruppo guidato da Iqbal riuscì a rivoluzionare la produzione di un composto che stava acquisendo una rilevanza strategica crescente. L'ottimizzazione dei parametri operativi e l’attenta selezione dei precursori permisero di superare le criticità legate alle basse rese delle sintesi precedenti." - } - ] - } - ], - "index": 61 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Questo progresso non ha solo ridefinito l'efficacia chimica del processo, ma ne ha confermato la fattibilità su scala industriale, garantendo un ottimo equilibrio tra efficienza sintetica (atom economy) e sostenibilità economica." - } - ] - } - ], - "index": 62 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Successivamente, nel 1987, il gruppo di ricerca di Closs e Gompper" - }, - { - "type": "text", - "content": "8 ", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "propose un nuovo metodo di sintesi dei DPP a partire da succindiammidi e della N,N-dimetilbenzammide dietilacetale, visibile in " - }, - { - "type": "text", - "content": "Figura 9", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 63 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Un'attenta ottimizzazione del processo sintetico ha permesso di massimizzare la produzione del DPP " - }, - { - "type": "text", - "content": "3", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " raggiungendo un'efficienza globale di circa il 60%. Nella fase iniziale, scaldando i reagenti sopra citati, si genera il prodotto desiderato in quota minoritaria (30%). Tuttavia, l'isolamento della fase liquida residua consente di recuperare l’intermedio " - }, - { - "type": "text", - "content": "10", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", la succinilbenzimmidina, con un'abbondanza del 35%. L'aggiunta di potassio ter-butossido a quest'ultimo composto, in presenza di THF, ne induce una conversione quantitativa verso l'analogo DPP, raddoppiando di fatto le rese finali." - } - ] - } - ], - "index": 64 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 65, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 9 - sintesi del DPP3 proposta da Gloss e Gompper", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 66, - "type": "image_caption" - } - ], - "index": 65 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Una variante metodologica all'approccio classico, anche questo descritto da Iqbal et al." - }, - { - "type": "text", - "content": "5", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ", prevede il passaggio attraverso i tetraidrodichetopirrolopirroli, i quali vengono sottoposti a un processo di deidrogenazione per generare il nucleo DPP finale. Il reagente selezionato per promuovere quest'ultima fase è solitamente il DDQ (2,3-dicloro-5,6-dicianobenzochinone)." - } - ] - } - ], - "index": 67 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 68, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 10 - DDQ (2,3-dicloro-5,6-dicianobenzochinone)", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 69, - "type": "image_caption" - } - ], - "index": 68 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le vie sintetiche per accedere ai precursori tetraidrati sono molteplici; un approccio ampiamente noto, ad esempio, è quello introdotto da Sprake" - }, - { - "type": "text", - "content": "6", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ", che si basa sulla condensazione di una immina (" - }, - { - "type": "text", - "content": "11", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") con un estere succinico. L'intermedio " - }, - { - "type": "text", - "content": "12", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " così isolato viene infine convertito nel dichetopirrolopirrolo " - }, - { - "type": "text", - "content": "13 ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "mediante l'azione ossidativa del DDQ." - } - ] - } - ], - "index": 70 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 71, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 11 - esempio di sintesi proposta da Sprake et al.", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "6", - "style": [ - "italic", - "superscript" - ] - } - ] - } - ], - "index": 72, - "type": "image_caption" - } - ], - "index": 71 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'ottimizzazione di questi passaggi finali è stata oggetto di numerose indagini, tra cui spiccano i fondamentali contributi di ricercatori come Stas" - }, - { - "type": "text", - "content": "9", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ", Avcibasi" - }, - { - "type": "text", - "content": "10", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ", Riggs" - }, - { - "type": "text", - "content": "11", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " e Qian" - }, - { - "type": "text", - "content": "12", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 73 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Infine, un’ulteriore via sintetica per la produzione di queste molecole è rappresentata dal metodo sviluppato nel 1996 da Langhals et al." - }, - { - "type": "text", - "content": "13", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ". In questo caso, gli autori hanno dimostrato la possibilità di generare con successo i DPP sfruttando abilmente la reattività dei composti basati sul nucleo del furo[3,4-c]furandione." - } - ] - } - ], - "index": 74 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'intermedio furofurandionico (" - }, - { - "type": "text", - "content": "17", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") viene ottenuto per via termica in toluene" - }, - { - "type": "text", - "content": "14", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ", oppure sottoponendo specifici benzoilacetati a un accoppiamento radicalico/ossidativo mediato da miscele di iodio/sodio, con successiva chiusura termica dell'anello" - }, - { - "type": "text", - "content": "15", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " (" - }, - { - "type": "text", - "content": "Figura 12", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 75 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 76, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 12 - metodi di sintesi per ottenere il nucleo furo[3,4-c]furandione", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 77, - "type": "image_caption" - } - ], - "index": 76 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il metodo che si basa sugli intermedi furofurandionici, mostrato in " - }, - { - "type": "text", - "content": "Figura 13", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", viene utilizzato nella preparazione di composti N-arilati simmetrici (" - }, - { - "type": "text", - "content": "20", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") asimmetrici (" - }, - { - "type": "text", - "content": "19", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), e con catene alchiliche (" - }, - { - "type": "text", - "content": "21", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 78 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 79, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 13 - sintesi dei N-aril-DPP proposta da Langhals et al.", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 80, - "type": "image_caption" - } - ], - "index": 79 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Di seguito si riporta uno schema riassuntivo di tutte le sintesi per la formazione di dichetopirrolopirroli riportate in questo capitolo (" - }, - { - "type": "text", - "content": "Figura 14", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 81 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 82, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 14 - schema riassuntivo dei metodi sintetici analizzati per ottenere un dichetopirrolopirrolo", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 83, - "type": "image_caption" - } - ], - "index": 82 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Struttura e reattività ", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 84, - "anchor": "_Toc242438065", - "is_numbered_style": true, - "level": 3, - "section_number": "1.1.2" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le particolari proprietà chimico-fisiche dei dichetopirrolopirroli derivano direttamente dal loro sistema biciclico lattamico, un core a otto elettroni π perfettamente planare nel caso del DPP non sostituito. Questa geometria favorisce l'instaurarsi di un fitto network di interazioni intermolecolari. Da un lato, la formazione di legami a idrogeno (0,182 nm)" - }, - { - "type": "text", - "content": "16", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " porta alla costituzione di aggregati stabili, limitando drasticamente la solubilità del composto nei solventi organici convenzionali. Dall'altro, l'estesa coniugazione elettronica e la vicinanza spaziale tra i piani molecolari (0,334 nm)" - }, - { - "type": "text", - "content": "16 ", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "provocano un'ottimale sovrapposizione degli orbitali, generando intense interazioni di π-π stacking" - }, - { - "type": "text", - "content": "17", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ". Questo si traduce in una grande stabilità termica dei DPP, con un punto di fusione superiore a 350 °C ed una temperatura di degradazione che supera i 500 °C." - } - ] - } - ], - "index": 85 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le interazioni intermolecolari influenzano in modo significativo anche le proprietà ottiche, le quali variano in funzione dello stato di aggregazione del campione. Mettendo a confronto le analisi spettroscopiche effettuate in soluzione con quelle allo stato solido, si osserva in quest'ultimo caso un allargamento della banda di assorbimento accompagnato da un marcato effetto batocromico, con uno spostamento del picco di assorbimento di circa 30 nm (" - }, - { - "type": "text", - "content": "Figura 15", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")" - }, - { - "type": "text", - "content": "18", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 86 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/0cc8ba45ecb7b78a0f389ecdf2e753a48bf05e7d52a2f1ec0bd87a3a20cf2043.png" - } - ] - } - ], - "index": 87, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 15 - spettro di assorbimento del DPP non sostituito in film con spessore di 1200 Å (linea tratteggiata) ", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 88, - "type": "image_caption" - } - ], - "index": 87 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "e DPP non sostituito in DMSO (linea continua)", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 89 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le proprietà ottiche possono essere modulate agendo sulla natura elettronica dei sostituenti. Ad esempio, la funzionalizzazione del core dichetopirrolopirrolico con gruppi aventi caratteristiche elettroniche differenti (presenza simultanea di gruppi elettron-donatori ed elettron-attrattori) promuove un marcato effetto batocromico, ovvero una transizione dell’assorbimento verso lunghezze d'onda maggiori, insieme ad un aumento dell'intensità di assorbimento e a un allargamento della differenza tra i picchi di assorbimento e di emissione (Stokes shift)" - }, - { - "type": "text", - "content": "19", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 90 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In " - }, - { - "type": "text", - "content": "Tabella 2", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", si riportano le proprietà fotofisiche di dichetopirrolopirroli con diversi sostituenti." - } - ] - } - ], - "index": 91 - }, - { - "type": "table", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tabella 2 - proprietà foto-fisiche di DPP con diversi sostituenti in soluzione e allo stato solido", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "20", - "style": [ - "italic", - "superscript" - ] - } - ] - } - ], - "index": 92, - "type": "table_caption" - }, - { - "lines": [ - { - "spans": [ - { - "type": "table", - "html": "

R

Colore a

λ absmax (nm)

ε max d (M-1 cm-1)

Soluzione b

Solido c

3-CF3

Giallo-arancio

509

518

21000

3-Cl

Arancione

512

528

27000

H

Giallo-rosso

504

538

33000

4-Br

Blu-rosso

515

555

35000

4-NMe2

Viola-blu

554

603

81500

" - } - ] - } - ], - "index": 93, - "type": "table_body" - } - ], - "index": 93 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "a", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " soluzione in NMP, " - }, - { - "type": "text", - "content": "b", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " soluzione in DMSO," - }, - { - "type": "text", - "content": " c ", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "ottenuto mediante misure di riflettanza" - } - ] - } - ], - "index": 94 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "su un film di PVC pigmentato, " - }, - { - "type": "text", - "content": "d", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " in DMSO" - } - ] - } - ], - "index": 95 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I dati evidenziano uno shift batocromico tra lo spettro in soluzione e quello in fase solida. La spiegazione di questo fenomeno sta nella formazione di legami a idrogeno intermolecolari: l’atomo di idrogeno del gruppo ammidico, infatti, è in grado di interagire con il doppietto dell’atomo di ossigeno del gruppo carbonilico di una molecola adiacente. Questo provoca uno spostamento della densità elettronica sull’atomo di azoto, che allo stato solido porta alla formazione di una parziale carica negativa che influenza la struttura elettronica con variazione delle lunghezze d’onda di assorbimento ed i corrispettivi massimi" - }, - { - "type": "text", - "content": "20", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 96 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'analisi dei diversi dichetopirrolopirroli in " - }, - { - "type": "text", - "content": "Tabella 2 ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "mostra come le proprietà ottiche siano strettamente dipendenti dai sostituenti aromatici, con un generale effetto batocromico dello spettro di emissione in soluzione rispetto al DPP avente gruppi aromatici non sostituiti. Rispetto alla molecola di base (DPP non sostituito), qualsiasi modifica strutturale si traduce, in Il comportamento allo stato solido appare, invece, fortemente dipendente dalla posizione dei sostituenti sull’anello aromatico portando ad effetti di natura prettamente sterica. L'ingombro generato modifica l'angolo di torsione dei gruppi aromatici rispetto al core, alterando di conseguenza la fotofisica del sistema. Mentre la funzionalizzazione in posizione para minimizza l'ingombro sterico e mantiene lo spostamento verso lunghezze d'onda maggiori, l'inserimento di gruppi in posizione meta provoca un aumento dell'angolo di torsione, riducendo la coniugazione effettiva e inducendo uno shift ipsocromico. Risulta essenziale specificare questa dinamica per distinguere chiaramente il contributo \"strutturale\" da quello elettronico, sebbene la posizione sull'anello influenzi inevitabilmente anche quest'ultimo." - } - ] - } - ], - "index": 97 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Per quanto riguarda gli effetti elettronici, i gruppi moderatamente elettron-attrattori provocano cambiamenti spettrali limitati, con picchi di assorbimento racchiusi in un range ristretto (504-515 nm). Al contrario, la presenza di un gruppo fortemente elettron-donatore (come il gruppo 4-NMe₂) produce un netto spostamento del massimo di assorbimento, di circa 50 nm. Questa marcata variazione è la diretta conseguenza di un'architettura elettronica di tipo donatore-accettore-donatore (push-pull-push): essendo il core DPP intrinsecamente elettron-povero, il collegamento con sostituenti ricchi di elettroni modifica la densità di carica lungo il sistema coniugato, alterandone l'assorbimento fotonico." - } - ] - } - ], - "index": 98 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La spiccata sensibilità del core centrale alla natura dei sostituenti periferici trova giustificazione, secondo Lenz" - }, - { - "type": "text", - "content": "20", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ", nella geometria di queste molecole. Analisi strutturali rivelano infatti che i gruppi fenilici subiscono una torsione di appena 7° rispetto al piano del nucleo del DPP. Questa piccola variazione risulta sorprendente se si considera la notevole repulsione sterica che si instaura tra i protoni in posizione orto dell'anello benzenico e gli eteroatomi (ossigeno e gruppi amminici) dell'anello lattamico. La conservazione della planarità si spiega mediante una delocalizzazione π che unisce le unità benzeniche allo scheletro centrale. Una prova tangibile di questa forte coniugazione elettronica è fornita dalla distanza interatomica del legame di giunzione tra il fenile e il nucleo: misurando solamente 1,46 Å, risulta nettamente più corto di un canonico legame singolo (generalmente atteso nel range di 1,50–1,54 Å), suggerendo un carattere di parziale doppio legame" - }, - { - "type": "text", - "content": "20", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 99 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/6f340ba76a30783ab8d6f8f0f47a136adeaf5193281bb3fae385c513191005ea.png" - } - ] - } - ], - "index": 100, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 16 - struttura cristallina del DPP3 (distanze in Å)", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "16", - "style": [ - "italic", - "superscript" - ] - } - ] - } - ], - "index": 101, - "type": "image_caption" - } - ], - "index": 100 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In conclusione, la straordinaria sensibilità dello spettro di assorbimento rispetto ai sostituenti non è altro che la conseguenza di un’elevata coniugazione della struttura, dove ogni minima variazione elettronica indotta sugli anelli periferici si traduce in una ridistribuzione della carica complessiva sull'intero scheletro molecolare." - } - ] - } - ], - "index": 102 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Per quanto riguarda la reattività dei DPP, invece, questa risulta essere varia per via dei diversi centri reattivi e del grande numero di sostituenti che posso essere introdotti nell’anello aromatico" - }, - { - "type": "text", - "content": "7", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 103 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In " - }, - { - "type": "text", - "content": "Figura 17 ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "è possibile osservare i vari gruppi funzionali coinvolti nella reattività dei DPP." - } - ] - } - ], - "index": 104 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 105, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 17 - reattività dei dichetopirrolopirroli", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "2", - "style": [ - "italic", - "superscript" - ] - } - ] - } - ], - "index": 106, - "type": "image_caption" - } - ], - "index": 105 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Si distinguono due macrocategorie di siti reattivi: quelli che possono essere coinvolti da un attacco nucleofilo e quelli che, invece, possiedono un carattere nucleofilo e che, quindi, possono attaccare un elettrofilo. I primi sono essenzialmente i carbonili ammidici (" - }, - { - "type": "text", - "content": "a", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") e i due atomi di carbonio in posizione 3 e 6 che possono subire addizione di Michael (" - }, - { - "type": "text", - "content": "b", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), oltre ad eventuali reazioni sugli anelli aromatici che possiedano gruppi elettron-attrattori in determinate posizioni (" - }, - { - "type": "text", - "content": "c", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", " - }, - { - "type": "text", - "content": "d", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "). Al contrario, i gruppi nucleofili sono l’atomo di ossigeno del carbonile (" - }, - { - "type": "text", - "content": "e", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), che a seguito di tautomeria può risultare un ottimo nucleofilo, l’atomo di azoto del lattame (" - }, - { - "type": "text", - "content": "f", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), che a seguito della deprotonazione è in grado di attaccare un elettrofilo; si possono avere reazioni di SNAr sugli anelli aromatici in posizione 3 e 6 (" - }, - { - "type": "text", - "content": "g", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), grazie all’effetto elettron-attrattore che possiede il core dichetopirrolopirrolico, oppure ancora reazioni su elettrofili partendo da funzionalità nucleofile già presenti sugli anelli aromatici (" - }, - { - "type": "text", - "content": "h", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "). Infine, è possibile effettuare sintesi di oligomeri o polimeri mediante reazioni di cross-coupling (" - }, - { - "type": "text", - "content": "i", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") partendo da DPP alogenati insieme ai corrispondenti reattivi organometallici, permettendo, in questo modo, di estendere ulteriormente la coniugazione." - } - ] - } - ], - "index": 107 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Nei paragrafi successivi sono riportate le reazioni che più comunemente vengono effettuate su questa famiglia di molecole, alcune delle quali utilizzate nel corso dell’attività sperimentale svolta." - } - ] - } - ], - "index": 108 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Reazioni su gruppi ammidici come nucleofili ", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 109 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Una delle reazioni più comuni che viene effettuata sui dichetopirrolopirroli è la sostituzione nucleofila, favorita dalla presenza di gruppi ammidici, facilmente deprotonabili mediante l’utilizzo di basi forti." - } - ] - } - ], - "index": 110 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 111, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 18 - deprotonazione stabilizzata per risonanza mesomerica del DPP", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 112, - "type": "image_caption" - } - ], - "index": 111 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La carica negativa non è solo distribuita tra gli atomi di azoto e ossigeno dello stesso gruppo ammidico (" - }, - { - "type": "text", - "content": "22", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " e " - }, - { - "type": "text", - "content": "23", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") ma può essere spostata anche al secondo atomo di ossigeno, dando la struttura mesomerica (" - }, - { - "type": "text", - "content": "24", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), che contiene un’unità pirrolica aromatica. Quindi, essendo l’anione fortemente stabilizzato, l’acidità dei protoni ammidici è relativamente elevata." - } - ] - } - ], - "index": 113 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La reazione viene influenzata dai sostituenti presenti sugli anelli aromatici, sia per effetto sterico, sia per effetti mesomerici sulla carica negativa generata dalla deprotonazione; inoltre vanno a modificare la solubilità del DPP." - }, - { - "type": "text", - "content": "21 ", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "Proprio la scarsa solubilità della molecola rappresenta un ostacolo alla reazione, è quindi necessario l’utilizzo di solventi che siano in grado di solubilizzarla almeno parzialmente. I solventi polari aprotici sono particolarmente adatti a questo scopo e la N,N-dimetilformammide (DMF) è quella più utilizzata." - } - ] - } - ], - "index": 114 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il più comune obiettivo di questa reazione è quello di introdurre catene alchiliche sull’azoto per modificarne la solubilità, eliminando i legami a idrogeno che tipicamente formano i gruppi ammidici. È stato studiato come l’aggiunta di un semplice gruppo metile al DPP aumenti la solubilità di 27 volte in DMF." - }, - { - "type": "text", - "content": "5", - "style": [ - "superscript" - ] - } - ] - } - ], - "index": 115 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In letteratura sono riportati molti studi in cui la reazione di sostituzione nucleofila viene utilizzata per la protezione delle funzionalità ammidiche, mediante l’utilizzo di gruppi ter-butossicarbonilici (Boc)." - }, - { - "type": "text", - "content": "22", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " L’introduzione di questi ultimi provoca un aumento della solubilità del prodotto e, mediante decomposizione termica, possono essere rimossi facilmente per ottenere il DPP non protetto in modo quantitativo (" - }, - { - "type": "text", - "content": "Figura 19", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 116 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 117, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 19 - reazione di protezione e deprotezione con gruppo Boc", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 118, - "type": "image_caption" - } - ], - "index": 117 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Grazie a questa proprietà, i DPP protetti da Boc possono essere usati come pigmenti “latenti”, ad esempio per la colorazione dei polimeri" - }, - { - "type": "text", - "content": "23,24", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ". Grazie alla sua buona solubilità, questo pigmento riesce ad essere distribuito omogeneamente nel materiale polimerico. La matrice contenente il cromoforo viene poi riscaldata, portando alla formazione di un materiale colorato con pigmento di DPP non protetto di partenza." - } - ] - } - ], - "index": 119 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Sono inoltre riportati in letteratura alcuni esempi di reazioni di sostituzione nucleofila aromatico (SNAr) in cui l’azoto ammidico funge da nucleofilo. Questa tipologia di reazione, però, funziona in modo efficace solo quando l’agente arilante è un fluoroarene molto elettron-povero, ad esempio 1-fluoro-2,4-dinitrobenzene, mentre reazioni con arili meno elettron-poveri, come il 4-nitrofluorobenzene, o con un alogeno diverso dal fluoro, non portano alla formazione del prodotto desiderato. Recentemente Würthner ed i suoi collaboratori hanno dimostrato che la reazione SNAr dei DPP può essere eseguita anche utilizzando l’1-fluoro-2-nitro-4-(trifluorometil)benzene come agente arilante." - }, - { - "type": "text", - "content": "23", - "style": [ - "superscript" - ] - } - ] - } - ], - "index": 120 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Reazioni sugli anelli aromatici", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 121 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Sebbene non strettamente parte del core dichetopirrolopirrolico, la maggior parte dei DPP presenti in letteratura contengono sostituenti aromatici derivanti dai benzonitrili di partenza e vengono quindi considerati parte integrante della struttura. I sostituenti arilici, in particolare, possono subire reazioni tipiche dei composti aromatici, come sostituzioni elettrofile aromatiche (S" - }, - { - "type": "text", - "content": "e", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "Ar)." - } - ] - } - ], - "index": 122 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Ad esempio, il DPP ottenuto mediante l’utilizzo di benzonitrile (" - }, - { - "type": "text", - "content": "3", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), può essere solfonato con acido solforico fumante, ottenendo il DPP " - }, - { - "type": "text", - "content": "26", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " contenente gruppi solfonici nelle posizioni para degli anelli benzenici (" - }, - { - "type": "text", - "content": "Figura 20", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "). Il DPP " - }, - { - "type": "text", - "content": "3", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " può reagire anche con il bromo ed il cloro gassosi, producendo due molecole completamente diverse: mediante l’uso di bromo si provoca una sostituzione elettrofila aromatica ottenendo il DPP " - }, - { - "type": "text", - "content": "27", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " para-dibromurato, mentre utilizzando il cloro si ottiene il prodotto in cui quest’ultimo viene addizionato ai doppi legami dell’unità centrale di DPP (" - }, - { - "type": "text", - "content": "28", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "). Sebbene la bromurazione del DPP " - }, - { - "type": "text", - "content": "3", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " abbia una buona resa, superiore all’80%, il DPP " - }, - { - "type": "text", - "content": "26", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " si può ottenere più semplicemente partendo dal 4-bromobenzonitrile utilizzando il metodo di Iqbal riportato nella sezione precedente." - } - ] - } - ], - "index": 123 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 124, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 20 - reazioni di sostituzione elettrofile aromatiche sugli anelli del DPP ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "3", - "style": [ - "bold", - "italic" - ] - } - ] - } - ], - "index": 125, - "type": "image_caption" - } - ], - "index": 124 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Una delle reazioni più utili per le successive funzionalizzazioni è la bromurazione dei DPP N-N’-disostituiti che, nelle posizioni 3 e 6, possiedono sostituenti eteroaromatici come tiofene, furano o selenofene (" - }, - { - "type": "text", - "content": "Figura 21", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "). A causa della loro alta densità elettronica, questi eterocicli reagiscono facilmente con NBS per dare i corrispondenti derivati bromurati con buone rese. La bromurazione del DPP " - }, - { - "type": "text", - "content": "29", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " e " - }, - { - "type": "text", - "content": "30", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " può essere effettuata anche utilizzando bromo elementare." - } - ] - } - ], - "index": 126 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 127, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 21 - bromurazione del DPP con sostituenti eteroaromatici in posizione 3 e 6", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 128, - "type": "image_caption" - } - ], - "index": 127 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La sintesi dei DPP " - }, - { - "type": "text", - "content": "32", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", " - }, - { - "type": "text", - "content": "33", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " e " - }, - { - "type": "text", - "content": "34 ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "è difficile da realizzare mediante il metodo che sfrutta gli esteri succinici combinati con i corrispondenti nitrili: questo è dovuto al fatto che, in condizioni fortemente basiche, gli atomi di bromo in questi nitrili subiscono facilmente sostituzione nucleofila, riducendo le rese e complicando il processo di purificazione dei prodotti desiderati." - } - ] - } - ], - "index": 129 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il gruppo di ricerca di Gryko et al." - }, - { - "type": "text", - "content": "7", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " ha proposto un diverso esempio di sostituzione elettrofila aromatica: i DPP con sostituenti aromatici elettron-ricchi possono essere alchilati in DMF usando K" - }, - { - "type": "text", - "content": "2", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "CO" - }, - { - "type": "text", - "content": "3", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": " come base e tetrabutilammonio bisolfato (TBAHS) come catalizzatore a trasferimento di fase (" - }, - { - "type": "text", - "content": "Figura 22", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "). Questa reazione porta alla formazione didiacetali (" - }, - { - "type": "text", - "content": "35", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") che possono essere trasformati nei rispettivi derivati carbonilici mediante un acido forte di Brønsted, attivando quindi una reazione di ciclizzazione elettrofila da parte dell’anello aromatico elettron-ricco adiacente. In questo modo sono riusciti ad ottenere dei pigmenti composti da almeno sei anelli fusi π coniugati con particolari caratteristiche fotofisiche (" - }, - { - "type": "text", - "content": "36", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 130 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "35", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 131 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "36", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 132 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/44b209b21a14fccafd0091eceef379c4880287252f88a1e9934252c1085ed8ee.jpg" - } - ] - } - ], - "index": 133, - "type": "image_body" - } - ], - "index": 133 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/922a3a6b2ebac21c6502b6fa7ed720a1df107fd86ca9b2a71411a92192b8be29.png" - } - ] - } - ], - "index": 134, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 22 - reazione di ciclizzazione mediante sostituzione elettrofila aromatica sui DPP studiata da Gryko et al.", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "7 ", - "style": [ - "italic", - "superscript" - ] - } - ] - } - ], - "index": 135, - "type": "image_caption" - } - ], - "index": 134 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Un’altra importante categoria di reazioni che viene utilizzata per la modifica degli anelli aromatici è quella del cross coupling catalizzato da palladio. In particolare, i composti " - }, - { - "type": "text", - "content": "32", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", " - }, - { - "type": "text", - "content": "33 34", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " e " - }, - { - "type": "text", - "content": "37 ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "vengono utilizzati come descritto in " - }, - { - "type": "text", - "content": "Figura 23", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 136 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Queste reazioni solitamente presentano alte rese e portano alla sostituzione degli atomi di bromo nei composti citati con i corrispondenti gruppi arilici, alchilici e amminici." - } - ] - } - ], - "index": 137 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Oltre a fornire un sistema π espanso, le reazioni di cross coupling possono essere utilizzate per la sintesi di polimeri π coniugati a base di DPP. In questo caso specifico, le reazioni più utilizzate sono quelle di Suzuki e Stille." - } - ] - } - ], - "index": 138 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "alchil, aril, acil" - } - ] - } - ], - "index": 139 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "aril, alchil" - } - ] - } - ], - "index": 140 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "32", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 141 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "33", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 142 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "34", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 143 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "37", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 144 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Reagente Reazione ", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 145 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/ec1d0d99168054a309b5dc913893f65f3cfa6dc850c4c629c7b434cdf8638ac5.png" - } - ] - } - ], - "index": 146, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 23 - reazioni di cross coupling catalizzate da Pd sui DPP", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 147, - "type": "image_caption" - } - ], - "index": 146 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Diversi composti aromatici bifunzionali possono essere polimerizzati con i DPP bromurati " - }, - { - "type": "text", - "content": "32", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "-" - }, - { - "type": "text", - "content": "34", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " e " - }, - { - "type": "text", - "content": "37", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " in presenza di catalizzatori a base di palladio, fornendo i corrispettivi prodotti con buone rese (" - }, - { - "type": "text", - "content": "Figura 24", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 148 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "32", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 149 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "33", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 150 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "34", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 151 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "37", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 152 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/8b3b485d4581689998b33430f9592ff5b7d3e41f929230ba0626ae4d6f15b6d5.png" - } - ] - } - ], - "index": 153, - "type": "image_body" - } - ], - "index": 153 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "X", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " = S, O, Se, -CH=CH-; " - }, - { - "type": "text", - "content": "Y", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " = B(OH)" - }, - { - "type": "text", - "content": "2", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ", B(OAlc)" - }, - { - "type": "text", - "content": "2", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ", SnAlc" - }, - { - "type": "text", - "content": "3", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "; " - }, - { - "type": "text", - "content": "R", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "1", - "style": [ - "bold", - "superscript" - ] - }, - { - "type": "text", - "content": " = alchile, arile, acile; " - }, - { - "type": "text", - "content": "R", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "2", - "style": [ - "bold", - "superscript" - ] - }, - { - "type": "text", - "content": " = H, alchile, OAlchile" - } - ] - } - ], - "index": 154 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 24 - sintesi generica di polimeri a base di DPP mediante reazioni di cross coupling", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 155 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In " - }, - { - "type": "text", - "content": "Figura 24", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", in particolare, sono stati utilizzati come co-monomeri i derivati di composti aromatici elencati: tiofene, 2,2'-bitienile, naftalene, 9,9-dialchilafluorene, tienotiofene, benzene, N-alchilcarbazolo." - } - ] - } - ], - "index": 156 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Per ottenere polimeri con buona solubilità e processabilità vengono utilizzati come materiali di partenza DPP con sostituenti alifatici a catena lunga o ramificati. Solitamente queste molecole sono polimerizzate con composti aromatici ricchi di elettroni, come quelli elencati in " - }, - { - "type": "text", - "content": "Figura 24", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", quindi, a causa del carattere elettron-accettore dell’unità dichetopirrolopirrolica, i polimeri che si ottengono sono di tipo donatore-accettore. Questa struttura generalmente garantisce buone proprietà conduttive, in particolare alta mobilità di carica e banda proibita a bassa energia, e consente l’applicazione del materiale in dispositivi semiconduttori come OFET e fotovoltaici organici (OPV)." - }, - { - "type": "text", - "content": "25,26 ", - "style": [ - "superscript" - ] - } - ] - } - ], - "index": 157 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le reazioni di cross coupling di Suzuki e Stille sono particolarmente efficienti per la sintesi di composti biarilici ma entrambe richiedono una pre-attivazione dei substrati, ovvero la presenza di gruppi funzionali reattivi come atomi di bromo nel primo e gruppi boronici o trialchilstannici nel secondo componente della reazione. Mentre l’introduzione di atomi di bromo è relativamente semplice, la sintesi di acidi o esteri boronici e reagenti organostannici è più complessa e richiede condizioni di reazione più drastiche e utilizzo di reagenti altamente reattivi come il butillitio (BuLi). Inoltre, diventa più complicata anche la purificazione delle miscele di reazione e il trattamento dei composti organostannici, altamente tossici." - } - ] - } - ], - "index": 158 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Proprio per questi motivi sono state studiate procedure alternative per la sintesi dei legami biarilici: tra i vari metodi indagati da Marder et al. i più utilizzati sono l’arilazione diretta e l’accoppiamento ossidativo di composti aromatici." - }, - { - "type": "text", - "content": "27,28 ", - "style": [ - "superscript" - ] - } - ] - } - ], - "index": 159 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L’arilazione diretta prevede l’accoppiamento di alogenuri arilici, spesso bromuri, con areni che non richiedono la pre-attivazione, in presenza di catalizzatori a base di palladio e basi. Durante la reazione uno dei gruppi CH del primo arene si condensa con l’unità legata al bromo (C-Br) del secondo componente, portando alla formazione di un nuovo legame arilico e acido bromidrico, che viene neutralizzato mediante l’azione della base. La regioselettività della reazione dipende dalla distribuzione della densità elettronica del reagente di partenza, dall’acidità degli atomi di idrogeno in ogni posizione e dalla presenza di eteroatomi o altri gruppi funzionali." - }, - { - "type": "text", - "content": "27 ", - "style": [ - "superscript" - ] - } - ] - } - ], - "index": 160 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 161, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 25 - reazione di arilazione diretta del DPP 29 con diversi bromoarili", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 162, - "type": "image_caption" - } - ], - "index": 161 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In due studi indipendenti, i gruppi di ricerca guidati da Marder e Chen" - }, - { - "type": "text", - "content": "29", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " hanno esplorato con successo le potenzialità di un particolare precursore DPP (" - }, - { - "type": "text", - "content": "29", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), impiegandolo come molecola di partenza per reazioni di arilazione diretta condotte in presenza di diversi bromoareni (" - }, - { - "type": "text", - "content": "Figura 25", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 163 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le condizioni di reazione prevedono la presenza di un catalizzatore costituito da acetato di palladio e acido pivalico, insieme a K" - }, - { - "type": "text", - "content": "2", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "CO" - }, - { - "type": "text", - "content": "3", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ", come base per neutralizzare HBr che si libera come coprodotto, e l’utilizzo di DMA come solvente; in questo modo si ottengono i prodotti " - }, - { - "type": "text", - "content": "38 (a-h)", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ". L’arilazione diretta ha luogo selettivamente nella posizione C5 dell’anello tiofenico, non sono stati identificati altri regioisomeri. Gryko et al. evidenziano come questo meccanismo di sintesi sia efficace sia con bromoareni elettron-ricchi sia con quelli elettron-poveri, anche quando il bromuro è il DPP stesso, in questo caso, però, si ottengono i prodotti con rese minori (" - }, - { - "type": "text", - "content": "Figura 26", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 164 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 165, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 26 - arilazione dei DPP di-brorumati con diversi areni", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 166, - "type": "image_caption" - } - ], - "index": 165 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Diversamente dall’arilazione diretta, l’arilazione ossidativa procede mediante l’attivazione dei legami C-H dei due reagenti e non richiede pre-attivazione dei materiali di partenza" - }, - { - "type": "text", - "content": "28", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ". Il legame biarilico è formato attraverso l’ossidazione di due gruppi C-H aromatici, attivati mediante il catalizzatore a base di palladio. Questo metodo è stato utilizzato da Marder per l’arilazione del DPP " - }, - { - "type": "text", - "content": "29", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ". La reazione con polifluorurati poveri di elettroni in presenza di Pd(OAc)" - }, - { - "type": "text", - "content": "2", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": " come catalizzatore e carbonato d’argento come ossidante ha fornito i corrispondenti derivati coniugati " - }, - { - "type": "text", - "content": "42 (a-c)", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 167 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 168, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 27 - reazione di arilazione ossidativa", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 169, - "type": "image_caption" - } - ], - "index": 168 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La resa migliore (79%) è stata ottenuta per il composto " - }, - { - "type": "text", - "content": "45a", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", sintetizzato da tetrafluoropiridina e DPP " - }, - { - "type": "text", - "content": "29", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 170 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Dallo studio dell'accoppiamento ossidativo con il DPP " - }, - { - "type": "text", - "content": "29", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " (" - }, - { - "type": "text", - "content": "Figura 27", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), emerge una minore reattività per substrati quali il pentafluorobenzene e il tetrafluorobenzonitrile, i quali restituiscono rese rispettivamente del 23% e del 45%. Questo approccio via attivazione C-H, seppur efficace, presenta una criticità rilevante: l'impiego massiccio di ossidanti, come Ag" - }, - { - "type": "text", - "content": "2", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "CO" - }, - { - "type": "text", - "content": "3", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ". In questo contesto, un'alternativa sintetica valida e notevolmente più economica per l'ottenimento di polimeri coniugati, in particolare per i derivati del DPP affiancati da anelli tiofenici (come il precursore " - }, - { - "type": "text", - "content": "29", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), è rappresentata dalla polimerizzazione ossidativa mediata da ferro tricloruro (FeCl" - }, - { - "type": "text", - "content": "3", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "). A differenza dei tradizionali cross-coupling catalizzati da palladio, questo metodo non richiede alcuna complessa e costosa pre-attivazione dei monomeri (come nel caso di alogenazione, borilazione o stannilazione) né l'impiego di metalli di transizione pregiati. La reazione procede tipicamente in solventi poco polari, dove il ferro tricloruro agisce sia come acido di Lewis sia da ossidante, innescando la formazione di radical cationi sugli anelli tiofenici che portano alla formazione del legame C-C e alla successiva crescita della catena polimerica (" - }, - { - "type": "text", - "content": "Figura 28", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 171 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 172, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 28 - meccanismo di polimerizzazione ossidativa mediante FeCl", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "3", - "style": [ - "italic", - "subscript" - ] - } - ] - } - ], - "index": 173, - "type": "image_caption" - } - ], - "index": 172 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Sebbene l'ossidazione chimica possa offrire un controllo minore sulla polidispersione e sulla regioregolarità rispetto alle più controllate reazioni di Suzuki o Stille, essa si conferma un approccio estremamente diretto e scalabile per la sintesi di polimeri a base di DPP, permettendo di ottenere materiali semiconduttori con eccellenti proprietà optoelettroniche." - } - ] - } - ], - "index": 174 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Un' ulteriore alternativa sintetica si basa sulla litiazione in posizione C5. Al pari di altri sistemi tiofenici, i DPP " - }, - { - "type": "text", - "content": "29", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", " - }, - { - "type": "text", - "content": "30", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " e " - }, - { - "type": "text", - "content": "31", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " (" - }, - { - "type": "text", - "content": "Figura 21", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") reagiscono prontamente con LDA, aprendo la strada a diverse funzionalizzazioni (" - }, - { - "type": "text", - "content": "Figura 29", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "). Come è possibile osservare nello schema, la reazione dell'intermedio litiato con formammidi (es. N-formilpiperidina o DMF) genera la dialdeide " - }, - { - "type": "text", - "content": "43", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "30", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ". Se invece si impiega 2-isopropossi-4,4,5,5-tetrametil-1,3,2-diossaborolano o cloruro di trimetilstagno, si ottengono rispettivamente il diestere boronico " - }, - { - "type": "text", - "content": "44", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "31", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " e lo stannano " - }, - { - "type": "text", - "content": "45", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "32", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ". Entrambi questi intermedi risultano di grande utilità per successivi step di cross coupling. Infine, è possibile isolare con buone rese il composto di-iodurato " - }, - { - "type": "text", - "content": "46", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "31", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " effettuando il quenching della reazione con iodio molecolare." - } - ] - } - ], - "index": 175 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/31ab95d1513571fe567fc67cef34b455944e7955aa5b495ee97b09788ef0f20b.png" - } - ] - } - ], - "index": 176, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 29 - reazione di litiazione e funzionalizzazione con successiva reazione con elettrofili", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 177, - "type": "image_caption" - } - ], - "index": 176 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Un’ultima tipologia di reazione a cui possono andare incontro i dichetopirrolopirroli è quella della sostituzione nucleofila aromatica (SNAr); in particolare la reazione avviene in assenza di catalizzatori a base di palladio e su DPP che possiedono dei buoni gruppi uscenti sugli anelli aromatici. Essendo il core di-lattamico del DPP un elettron-attrattore, in letteratura solo riportati numerosi esempi in cui i composti " - }, - { - "type": "text", - "content": "27", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " e " - }, - { - "type": "text", - "content": "47", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " reagiscono con diverse ammine secondarie. La reazione procede a temperature elevate in autoclave per dare i corrispondenti sistemi amminici " - }, - { - "type": "text", - "content": "48 (a-d)", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", come mostrato in " - }, - { - "type": "text", - "content": "Figura 30", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 178 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 179, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 30 - sostituzione aromatica classica su derivati di DPP", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 180, - "type": "image_caption" - } - ], - "index": 179 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Fluorescenza ", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 181, - "anchor": "_Toc242438066", - "is_numbered_style": true, - "level": 2, - "section_number": "1.2" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La fluorescenza è il fenomeno fisico corrispondente all’'emissione di fotoni da parte di una sostanza, in seguito al rilassamento da uno stato elettronico eccitato ad uno fondamentale." - } - ] - } - ], - "index": 182 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Per molto tempo, in seguito all'introduzione del termine \"fluorescenza\" da parte di G. G. Stokes a metà del XIX secolo, la distinzione tra fluorescenza e fosforescenza si è basata esclusivamente sulla durata dell'emissione al termine dell'eccitazione. Nello specifico, la fluorescenza veniva considerata come un'emissione luminosa destinata a svanire simultaneamente all'interruzione della sorgente eccitante, mentre nella fosforescenza la luce emessa persisteva anche in assenza dello stimolo iniziale. Tuttavia, un simile criterio risultava insufficiente. Esistono infatti fenomeni di fluorescenza a vita lunga (ad esempio, nei sali di europio bivalente) e di fosforescenza a vita breve (come la luminescenza violetta del solfuro di zinco) che esibiscono durate del tutto comparabili, nell'ordine delle centinaia di nanosecondi" - }, - { - "type": "text", - "content": "33", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 183 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "È stato poi determinato che ciò che distingue la fluorescenza dalla fosforescenza è la natura dello stato eccitato da cui decade l’elettrone." - } - ] - } - ], - "index": 184 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Negli stati eccitati di singoletto, l'elettrone promosso all'orbitale a maggiore energia mantiene uno spin opposto (accoppiato) rispetto a quello dell'elettrone rimasto nell'orbitale fondamentale. Di conseguenza, il rilassamento radiativo verso lo stato fondamentale è un processo permesso dalle regole di selezione dello spin e avviene rapidamente attraverso l'emissione di un fotone ad energia minore della radiazione incidente, e quindi a lunghezze d’onda maggiori. Si tratta di un fenomeno rapido, in cui il tempo di vita medio dello stato eccitato è nell’ordine delle decine di nanosecondi (10" - }, - { - "type": "text", - "content": "-9 ", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "s)." - } - ] - } - ], - "index": 185 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La fosforescenza, invece, consiste nell'emissione di radiazione luminosa a partire da stati eccitati di tripletto, nei quali l'elettrone promosso all'orbitale a maggiore energia presenta lo stesso orientamento di spin dell'elettrone rimasto nello stato fondamentale. Poiché le transizioni radiative verso lo stato fondamentale, che è uno stato di singoletto, sono proibite dalle regole di selezione dello spin, i tempi di vita medi della fosforescenza sono più lunghi, variando generalmente da pochi millisecondi a diversi secondi" - }, - { - "type": "text", - "content": "34", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 186 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I processi fotofisici che intercorrono tra l'assorbimento e la successiva emissione di luce vengono illustrati mediante il diagramma di Jablonski (" - }, - { - "type": "text", - "content": "Figura 31", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "). Questo schema rappresenta il punto di partenza fondamentale per qualunque trattazione teorica sull'assorbimento e sulla luminescenza molecolare." - } - ] - } - ], - "index": 187 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/0423680b2667a6ca184d8ad3cdedd412ef8ade40cfcede7807f2fb580886520c.jpg" - } - ] - } - ], - "index": 188, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 31 - diagramma di Jablonski", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 189, - "type": "image_caption" - } - ], - "index": 188 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In questo diagramma vengono rappresentati con delle frecce continue i fenomeni che coinvolgono l’interazione con una radiazione elettromagnetica, mentre con linee tratteggiate i fenomeni di rilassamento molecolare che non coinvolgono interazioni con la luce." - } - ] - } - ], - "index": 190 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In condizioni normali, l'assorbimento ottico coinvolge molecole che si trovano nel loro livello vibrazionale fondamentale. L'ampio divario energetico tra lo stato fondamentale (S" - }, - { - "type": "text", - "content": "0", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ") e il primo stato elettronico eccitato (S" - }, - { - "type": "text", - "content": "1", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ") impedisce la promozione di elettroni S" - }, - { - "type": "text", - "content": "0 ", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "a livelli energetici superiori tramite semplice energia termica; per questo motivo, per indurre la fluorescenza è necessaria l'eccitazione mediante radiazione luminosa." - } - ] - } - ], - "index": 191 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "A seguito dell'assorbimento di un fotone, il fluoroforo viene promosso a un livello vibrazionale superiore all'interno degli stati elettronici eccitati S" - }, - { - "type": "text", - "content": "1", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": " o S" - }, - { - "type": "text", - "content": "2. ", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "Tuttavia, quando si trova in fase condensata (liquida o solida), la molecola va incontro a un processo di rilassamento non radiativo molto rapido, dissipando energia fino a raggiungere il livello vibrazionale fondamentale dello stato S" - }, - { - "type": "text", - "content": "1. ", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "Questo fenomeno, definito conversione interna, avviene in intervalli temporali estremamente brevi, in genere nell'ordine dei picosecondi (10" - }, - { - "type": "text", - "content": "-12", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " s). Poiché i tempi di vita medi della fluorescenza sono di diversi ordini di grandezza superiori, la conversione interna termina prima che la molecola possa decadere emettendo radiazione. Di conseguenza, l'emissione fluorescente si origina nella quasi totalità dei casi dal livello vibrazionale a minore energia dello stato S" - }, - { - "type": "text", - "content": "1", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ", come stabilito dalla regola di Kasha" - }, - { - "type": "text", - "content": "35", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 192 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/51d97cca166f20d62feb7eafcf0e6978cce78dc1fc3979bfacfca33e9f949e47.png" - } - ] - } - ], - "index": 193, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 32 - schema rappresentativo del fenomeno di intersystem crossing", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 194, - "type": "image_caption" - } - ], - "index": 193 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le molecole che si trovano nello stato eccitato S" - }, - { - "type": "text", - "content": "1 ", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "possono, in alternativa, subire un'inversione di spin e transitare nel primo stato eccitato di tripletto, T" - }, - { - "type": "text", - "content": "1", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ", non raggiungibile direttamente. Questo processo non radiativo di conversione da S" - }, - { - "type": "text", - "content": "1", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": " a T" - }, - { - "type": "text", - "content": "1 ", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "prende il nome di intersystem crossing (ISC) ed è mostrato in " - }, - { - "type": "text", - "content": "Figura 32", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ". Dallo stato di tripletto a più bassa energia, la molecola può tornare allo stato fondamentale nuovamente tramite conversione interna oppure mediante fosforescenza." - } - ] - } - ], - "index": 195 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'efficienza dell'emissione fluorescente dipende dunque in gran parte dalla struttura chimica del fluoroforo; in particolare, è necessaria una elevata rigidità strutturale per evitare fenomeni di rilassamento non radiativi." - } - ] - } - ], - "index": 196 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/969645e072498bad2c11541585f144818b6fac3d00dcac7d99a610e639f482c1.png" - } - ] - } - ], - "index": 197, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 33 - Stati elettronici per molecole rigide e flessibili", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 198, - "type": "image_caption" - } - ], - "index": 197 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Nelle molecole poco flessibili, infatti, la geometria dello stato fondamentale e quella dello stato eccitato non presentano distorsioni significative; questo riduce significativamente la probabilità che l'energia assorbita venga dissipata sotto forma di calore attraverso movimenti vibrazionali. Di conseguenza, l'energia dello stato eccitato viene rilasciata quasi interamente sotto forma di luce. Le strutture molecolari ideali per massimizzare questo effetto sono quelle che presentano pochi gradi di libertà, come i sistemi coniugati e i composti aromatici. I dichetopirrolopirroli rientrano perfettamente in questa categoria: grazie al loro scheletro molecolare planare e al vasto sistema di elettroni delocalizzati, il rilassamento vibrazionale è fortemente limitato" - }, - { - "type": "text", - "content": "34", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 199 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La fluorescenza può essere caratterizzata mediante diversi parametri, tra cui gli shift di Stokes, i tempi di vita e la resa quantica." - } - ] - } - ], - "index": 200 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "1.2.1. Shift di Stokes", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 201, - "anchor": "_Toc242438067", - "is_numbered_style": false, - "level": 3 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Lo shift di Stokes rappresenta la differenza tra la lunghezza d'onda della luce assorbita da una molecola e la lunghezza d'onda della luce emessa dalla stessa molecola sotto forma di fluorescenza o fosforescenza (" - }, - { - "type": "text", - "content": "Figura 34", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")" - }, - { - "type": "text", - "content": "36", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 202 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/3b55b8e6baa286d4a2e34a5ddcb6e51ee6a680299da1dd74559056416644ed73.png" - } - ] - } - ], - "index": 203, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 34 - shift di Stokes", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "37", - "style": [ - "italic", - "superscript" - ] - } - ] - } - ], - "index": 204, - "type": "image_caption" - } - ], - "index": 203 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La minore energia registrata durante l'emissione è il risultato di una dissipazione energetica che avviene attraverso decadimenti di natura tipicamente vibrazionale. Questa differenza di energia, quantificata come la distanza in lunghezza d'onda tra i massimi degli spettri di assorbimento e di fluorescenza, rappresenta un parametro distintivo per ciascun fluoroforo." - } - ] - } - ], - "index": 205 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "1.2.2. Resa quantica ", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 206, - "anchor": "_Toc242438068", - "is_numbered_style": false, - "level": 3 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'efficienza del processo radiativo di un cromoforo è quantificata dalla resa quantica di fluorescenza (ϕ). A livello macroscopico, questo parametro è definito come la frazione tra i quanti di luce riemessi dal sistema e quelli originariamente assorbiti per popolare lo stato eccitato (" - }, - { - "type": "text", - "content": "Equazione 1", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "):" - } - ] - } - ], - "index": 207 - }, - { - "type": "interline_equation", - "lines": [ - { - "spans": [ - { - "type": "interline_equation", - "content": "\\phi =\\frac{n\\circ fotoni emessi}{n\\circ fotoni assorbiti}" - } - ] - } - ], - "index": 208 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Equazione 1 - resa quantica a livello macroscopico", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 209 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Dal punto di vista della cinetica fotofisica, la resa quantica descrive la competizione tra il rilassamento emissivo e le vie di de-eccitazione non radiative. Matematicamente, si esprime rapportando la costante cinetica del decadimento fluorescente (K" - }, - { - "type": "text", - "content": "f", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ") alla somma di tutte le costanti di velocità non radiative che governano lo svuotamento dello stato eccitato (K" - }, - { - "type": "text", - "content": "nr", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "), quali l'intersystem crossing o la conversione interna (" - }, - { - "type": "text", - "content": "Equazione 2", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "):" - } - ] - } - ], - "index": 210 - }, - { - "type": "interline_equation", - "lines": [ - { - "spans": [ - { - "type": "interline_equation", - "content": "\\phi =\\frac{K_{f}}{K_{f}+\\sum_{}^{}K_{nr}}" - } - ] - } - ], - "index": 211 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Equazione 2 - resa quantica in cinetica fotofisica", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 212 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il valore ϕ di è strettamente legato alla topologia elettronica e all'architettura molecolare. Transizioni ad alta energia come le σ → σ* inducono prevalentemente la fotodissociazione del legame spegnendo l'emissione, mentre le eccitazioni n → π* e, in misura ancora maggiore, π → π* garantiscono le efficienze radiative migliori. A tal fine, la progettazione molecolare gioca un ruolo cruciale: strutture rigide, ricche di insaturazioni, anelli aromatici e funzionalità carboniliche massimizzano la probabilità di emissione" - }, - { - "type": "text", - "content": "34", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ". Al contrario, un'eccessiva flessibilità conformazionale favorisce la dissipazione dell'energia termica tramite moti vibrazionali (conversione interna), abbattendo drasticamente la resa fluorescente" - }, - { - "type": "text", - "content": "38,39", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 213 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "1.2.3. Tempi di vita", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 214, - "anchor": "_Toc242438069", - "is_numbered_style": false, - "level": 3 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il tempo di vita dello stato eccitato è definito dal tempo medio che la molecola vi trascorre prima di tornare allo stato fondamentale. In generale, i fenomeni di fluorescenza avvengonoin tempi nell’ordine delle decine di nanosecondi. Il tempo di vita medio viene calcolato mediante la seguente equazione." - } - ] - } - ], - "index": 215 - }, - { - "type": "interline_equation", - "lines": [ - { - "spans": [ - { - "type": "interline_equation", - "content": "\\tau =\\frac{1}{K_{f}+\\sum_{}^{}K_{nr}}" - } - ] - } - ], - "index": 216 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Equazione 3 - tempo di vita medio", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 217 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "È bene ricordare che l’emissione è un processo casuale e che solamente poche molecole emettono fotoni esattamente a t = τ; quindi, è importante sottolineare che τ rappresenta un valore medio. Il tempo di vita di un fluoroforo in assenza di processi non radiativi è chiamato tempo di vita intrinseco o naturale e viene espresso mediante la seguente equazione." - } - ] - } - ], - "index": 218 - }, - { - "type": "interline_equation", - "lines": [ - { - "spans": [ - { - "type": "interline_equation", - "content": "\\tau _{n}=\\frac{1}{K_{f}}" - } - ] - } - ], - "index": 219 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Equazione 4 - tempo di vita intrinseco", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 220 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Questo parametro può anche essere calcolato mediante la misura del tempo di vita medio e della resa quantica, mediante l’equazione riportata successivamente." - } - ] - } - ], - "index": 221 - }, - { - "type": "interline_equation", - "lines": [ - { - "spans": [ - { - "type": "interline_equation", - "content": "\\tau _{n}=\\frac{\\tau }{Q}" - } - ] - } - ], - "index": 222 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Equazione 5 - correlazione tra tempo di vita intrinseco e resa quantica", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 223 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il tempo di vita, così come la resa quantica, dipende dalle costanti di velocità di decadimento radiativo (Γ) e non radiativo (K" - }, - { - "type": "text", - "content": "nr", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "). Ad esempio, esistono dei composti, noti come scintillatori, che presentano rese elevate e tempi di vita brevi (⁓1 ns) grazie ad alti valori di Γ; al contrario, i composti con valori di K" - }, - { - "type": "text", - "content": "nr ", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "elevati hanno una fluorescenza debole, ne sono un esempio i composti aromatici con gruppi -NO" - }, - { - "type": "text", - "content": "2.", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "34", - "style": [ - "superscript" - ] - } - ] - } - ], - "index": 224 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Utilizzo di fluorofori in materiali polimerici", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 225, - "anchor": "_Toc242438070", - "is_numbered_style": true, - "level": 2, - "section_number": "1.3" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'inserimento di fluorofori all'interno di un sistema macromolecolare richiede un accurato design molecolare, poiché l'architettura scelta ne influenza drasticamente le proprietà finali. La classificazione dei sistemi polimero-fluoroforo può essere suddivisa in diverse categorie strutturali ben distinte: ci sono le strutture host-guest, i sistemi polimerici main-chain, side-chain e cross-linked (" - }, - { - "type": "text", - "content": "Figura 35", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 226 - }, - { - "type": "table", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "table", - "html": "

a)

b)

c)

d)

" - } - ] - } - ], - "index": 227, - "type": "table_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 35 - sistemi polimerici con inserimento di fluorofori, in verde il polimero e in rosso le unità di fluoroforo,", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 228, - "type": "table_caption" - } - ], - "index": 227 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "a: sistema host-guest, b: sistema main-chain, c: sistema side-chain, d: sistema cross-linked", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 229 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I sistemi polimerici di tipo host-guest rappresentano l’approccio più semplice e immediato per la fabbricazione di materiali fluorescenti. In questa architettura, la molecola d’interesse, ovvero il fluoroforo (guest), non forma legami covalenti con il polimero ma viene fisicamente mescolata e dispersa all’interno di quest’ultimo (host). Considerando che l’interazione tra le due specie è puramente di natura fisica, questa tipologia di struttura offre una notevole versatilità, data dalla possibilità di impiegare diverse tipologie di additivi, e facilità di preparazione, consentendo di ottenere materiali fluorescenti evitando di dover sviluppare complesse vie sintetiche." - } - ] - } - ], - "index": 230 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tuttavia, l’assenza di un legame chimico diretto tra il fluoroforo e il polimero impone importanti limitazioni applicative. Il difetto principale risiede nella scarsa stabilità del sistema a lungo termine: all’aumentare della concentrazione le molecole del " - }, - { - "type": "text", - "content": "guest", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": " tendono a comportarsi in modo assimilabile a un comune additivo a basso peso molecolare, migrando gradualmente verso la superficie della matrice polimerica e aggregandosi. Questa progressiva migrazione innesca fenomeni di segregazione di fase e disomogeneità strutturale che portano alla perdita delle proprietà ottiche desiderate, come la diminuzione della resa quantica." - } - ] - } - ], - "index": 231 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Per via di queste problematiche, quindi, la stabilità del fluoroforo all'interno della matrice deve essere garantita dalla sinergia tra le interazioni secondarie (legami a idrogeno e dipolo-dipolo) con il polimero e l'impiego di host con elevata cristallinità e alta temperatura di transizione vetrosa (T" - }, - { - "type": "text", - "content": "g", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "), i quali immobilizzano la molecola " - }, - { - "type": "text", - "content": "guest", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": " riducendo la mobilità macromolecolare" - }, - { - "type": "text", - "content": "40,41", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 232 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Nei sistemi main-chain, il cromoforo è legato chimicamente come parte integrante della catena polimerica principale. La sintesi di queste architetture risulta più complessa, in quanto richiede l'impiego di monomeri fluorescenti opportunamente bifunzionalizzati e un controllo rigoroso della stechiometria e dei rapporti di reattività per evitare un'eccessiva vicinanza tra i cromofori, che porterebbe allo spegnimento della fluorescenza. Un approccio di grande successo in questo ambito è la strategia " - }, - { - "type": "text", - "content": "“", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "grafting from" - }, - { - "type": "text", - "content": "”", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": ", ampiamente esplorata da Wang et al." - }, - { - "type": "text", - "content": "42", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ". Utilizzando un derivato dichetopirrolopirrolico bifunzionalizzato con gruppi idrossilici (DPP-OH) come iniziatore, è stato possibile far crescere simmetricamente due catene di policaprolattone (PCL) tramite polimerizzazione per apertura d'anello (ROP), ottenendo un copolimero PCL-DPP-PCL." - } - ] - } - ], - "index": 233 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Nei sistemi side-chain, invece, le unità luminescenti non costituiscono lo scheletro centrale, ma sono connesse chimicamente come catene laterali alla catena polimerica principale. Per minimizzare l'ingombro sterico e favorire la mobilità locale, la progettazione di queste macromolecole prevede spesso l'inserimento di uno spaziatore flessibile tra il core polimerico e il fluoroforo; ciò contribuisce ad abbassare la T" - }, - { - "type": "text", - "content": "g", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": " e a limitare le interazioni indesiderate tra i cromofori adiacenti. La sintesi di questi sistemi può avvenire per polimerizzazione diretta, copolimerizzando un monomero funzionalizzato con altri co-monomeri (per garantire la giusta \"diluizione\" del fluoroforo e una buona processabilità), oppure per reazioni di post-polimerizzazione, ancorando il colorante a un polimero preformato. Un esempio classico di questa architettura è riportato nel lavoro di Lee et al." - }, - { - "type": "text", - "content": "43", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ", i quali hanno sintetizzato copolimeri radicalici aventi una catena principale di polimetilmetacrilato (PMMA) a cui sono stati legati lateralmente dei cromofori a base di carbazolo e fenilenvinilene. Questa architettura side-chain non solo ha garantito un'eccellente solubilità nei comuni solventi organici senza formazione di gel, ma ha anche permesso di modulare finemente il colore dell'emissione e le proprietà di trasporto di carica." - } - ] - } - ], - "index": 234 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Per ovviare al problema della mobilità delle catene polimeriche, che nel tempo può portare all'avvicinamento dei cromofori e al conseguente spegnimento della fluorescenza, una soluzione è rappresentata dai sistemi reticolati (cross-linked). In questa architettura, i fluorofori fungono da unità multifunzionali in grado di creare veri e propri ponti chimici tra le macromolecole. Se da un lato questo approccio àncora permanentemente i cromofori nella loro posizione spaziale prevenendone l'aggregazione, dall'altro l'eccessiva rigidità conferita al reticolo comporta notevoli svantaggi applicativi: i materiali ottenuti possiedono un modulo elastico maggiore, ma risultano molto più fragili, insolubili e caratterizzati da una difficile lavorabilità." - } - ] - } - ], - "index": 235 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Applicazioni ", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 236, - "anchor": "_Toc242438071", - "is_numbered_style": true, - "level": 2, - "section_number": "1.4" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Negli ultimi anni, i derivati del dichetopirrolopirrolo (DPP) hanno ampiamente trasceso il loro impiego originario come pigmenti commerciali, affermandosi in una vasta gamma di campi tecnologici avanzati che spaziano dai transistor organici a effetto di campo (OFET), al fotovoltaico, fino alle sonde fluorescenti per il bioimaging." - } - ] - } - ], - "index": 237 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tra queste molteplici applicazioni, l'impiego del DPP ha assunto una rilevanza cruciale nel settore dell'optoelettronica organica; grazie all'elevata stabilità termica e fotochimica, unita a un nucleo fortemente elettron-deficiente, questo cromoforo è diventato un elemento chiave per la progettazione di semiconduttori innovativi e dispositivi a emissione di luce." - }, - { - "type": "text", - "content": "44", - "style": [ - "superscript" - ] - } - ] - } - ], - "index": 238 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'optoelettronica comprende lo studio e lo sviluppo di dispositivi basati sull'interazione tra la radiazione elettromagnetica e i materiali semiconduttori, con lo scopo di ottenere la conversione di segnali elettrici in fotoni, come nei diodi a emissione di luce (OLED), o viceversa, come nel caso delle celle fotovoltaiche (OSC) e dei fotorivelatori (" - }, - { - "type": "text", - "content": "Figura 36", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 239 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/b5eeb7a523a478426c9115cb517438454b75741ad797e9ccacdccfb802d2dca1.jpg" - } - ] - } - ], - "index": 240, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 36 - rappresentazione schematica dei principi fisici alla base dei materiali optoelettronici: generazione di portatori di carica per assorbimento (sinistra) e ricombinazione radiativa per emissione (destra)", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 241, - "type": "image_caption" - } - ], - "index": 240 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Storicamente, questo settore tecnologico è stato dominato dall'impiego di semiconduttori inorganici rigidi, caratterizzati da reticoli cristallini altamente ordinati quali il silicio." - }, - { - "type": "text", - "content": "45", - "style": [ - "superscript" - ] - } - ] - } - ], - "index": 242 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tuttavia, negli ultimi decenni, la ricerca si è orientata in modo significativo verso lo sviluppo dell'optoelettronica organica, che sfrutta le proprietà chimico-fisiche di piccole molecole e polimeri con estesi sistemi π-coniugati. L'impiego di materiali organici in sostituzione delle tradizionali controparti inorganiche offre una serie di vantaggi tecnologici. Tra i principali punti di forza spiccano la notevole leggerezza e la flessibilità meccanica, che consentono l'integrazione di tali semiconduttori in dispositivi deformabili o pieghevoli, spaziando dai display di nuova generazione fino all'elettronica indossabile (wearable electronics)." - }, - { - "type": "text", - "content": "46 ", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "Inoltre, da un punto di vista chimico e ingegneristico, uno dei vantaggi più rilevanti risiede nella processabilità di questi materiali. A differenza del silicio, i polimeri coniugati possono essere depositati da soluzione a basse temperature impiegando tecniche ad alta resa e a basso costo, quali la deposizione per spin-coating o processi di stampa su larga scala. Questo approccio garantisce una drastica riduzione dei costi operativi rispetto ai complessi processi ad alta temperatura o in alto vuoto richiesti dalla tecnologia inorganica, promuovendo contestualmente un minor impatto ambientale e aprendo la strada a un'elettronica scalabile e sostenibile." - } - ] - } - ], - "index": 243 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Affinché tali materiali polimerici processabili possano essere impiegati efficacemente nei dispositivi optoelettronici, risulta indispensabile poter governare in modo preciso le loro proprietà ottiche ed elettroniche. Questo si traduce nella necessità di ingegnerizzare il band gap del materiale." - }, - { - "type": "text", - "content": "47", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " Negli attuali semiconduttori organici, la strategia sintetica d'elezione per ottenere un controllo accurato di tale parametro è l'approccio donatore-accettore (D-A). Questa architettura macromolecolare si basa sulla copolimerizzazione alternata di unità strutturali fortemente elettron-deficienti (accettori) e unità elettron-ricche (donatori) lungo lo scheletro " - }, - { - "type": "inline_equation", - "content": "\\pi" - }, - { - "type": "text", - "content": "-coniugato." - }, - { - "type": "text", - "content": "48 ", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "L'interazione tra questi due blocchi monomerici induce un'ibridazione dei rispettivi orbitali di frontiera: il livello HOMO del copolimero risultante è determinato principalmente dalla porzione elettron-donatrice, mentre il livello LUMO è governato dall'unità elettron-accettrice. Questo riposizionamento energetico intracatena promuove un marcato trasferimento di carica intramolecolare, il quale comporta una drastica riduzione del salto energetico e consente di centrare lo spettro di assorbimento e di emissione del polimero all'interno della regione visibile. " - }, - { - "type": "text", - "content": "49", - "style": [ - "superscript" - ] - } - ] - } - ], - "index": 244 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Nel caso specifico delle architetture polimeriche sviluppate in questo progetto di tesi, il nucleo fortemente elettron-accettore del dichetopirrolopirrolo è stato combinato con unità di 3-esiltiofene (3HT), impiegate per il loro spiccato carattere elettron-donatore. L'introduzione del monomero tiofenico non solo funge da partner elettronico ideale per ibridare gli orbitali di frontiera del DPP, ma, grazie alla presenza della catena alchilica laterale esilica, garantisce anche l'adeguata solubilità della macromolecola finale, preservandone la processabilità." - }, - { - "type": "text", - "content": "49 ", - "style": [ - "superscript" - ] - } - ] - } - ], - "index": 245 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La sinergia donatore-accettore (D-A) instaurata tra il nucleo di DPP e l'unità di 3HT permette di sintonizzare la struttura a bande del materiale, conferendogli i requisiti optoelettronici ottimali per un potenziale impiego come strato elettro-luminescente nei dispositivi OLED." - } - ] - } - ], - "index": 246 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Affinché le proprietà ottiche ed elettroniche dei polimeri D-A possano essere sfruttate tecnologicamente, è necessario implementare questi materiali all'interno di dispositivi a stato solido. Un diodo organico a emissione di luce (OLED) si basa su una complessa architettura multistrato, progettata con estrema precisione per ottimizzare l'iniezione, il trasporto e la ricombinazione delle cariche elettriche. Storicamente, i primi dispositivi organici a singolo strato presentavano efficienze estremamente ridotte a causa di un forte sbilanciamento tra la mobilità degli elettroni e quella delle lacune. Per ovviare a questo problema, i moderni OLED impiegano una struttura a sandwich comprendente molteplici film sottili specializzati." - } - ] - } - ], - "index": 247 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il cuore del dispositivo è costituito dallo strato emissivo (EML, Emissive Layer) interposto tra due elettrodi asimmetrici. Da un lato, il dispositivo è delimitato da un anodo trasparente, tipicamente costituito da ossido di indio-stagno (ITO), caratterizzato da un elevato lavoro di estrazione e trasparente alla luce visibile; dall'altro lato, è presente un catodo metallico a basso lavoro di estrazione, come leghe di alluminio, calcio o bario." - } - ] - } - ], - "index": 248 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Per abbassare le barriere energetiche all'interfaccia tra gli elettrodi e il polimero luminescente, vengono frapposti degli strati ausiliari denominati HTL (Hole Transport Layer) ed ETL (Electron Transport Layer) (" - }, - { - "type": "text", - "content": "Figura 37", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 249 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/a5b7997b8d326b7a48f255dfe64de8c53d58fa41be4e96680027c5d542706e8d.jpg" - } - ] - } - ], - "index": 250, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 37 - rappresentazione schematica dell'architettura OLED", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 251, - "type": "image_caption" - } - ], - "index": 250 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il meccanismo di elettroluminescenza si innesca quando viene applicata una differenza di potenziale ai capi degli elettrodi. Il campo elettrico generato forza il catodo a iniettare elettroni all'interno del livello LUMO dell'ETL, spingendoli verso il materiale emissivo. In modo simultaneo e speculare, l'anodo estrae elettroni dal livello HOMO dell'HTL, iniettando di fatto cariche positive, comunemente definite \"lacune\". A differenza dei classici semiconduttori inorganici, in cui le cariche si muovono liberamente all'interno di bande di conduzione delocalizzate nel reticolo cristallino, nei semiconduttori organici macromolecolari il trasporto di carica avviene attraverso un meccanismo quantistico, detto hopping, tra stati energetici localizzati lungo le catene polimeriche o tra catene adiacenti." - }, - { - "type": "text", - "content": "45 ", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "È in questa fase di conduzione che le caratteristiche chimico-strutturali del copolimero DPP-3HT si rivelano determinanti. La tendenza del nucleo fortemente planare del DPP a instaurare interazioni intermolecolari a corto raggio, promuove la formazione di domini microstrutturali ordinati durante la deposizione del film solido." - }, - { - "type": "text", - "content": "44", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " Una morfologia del film ordinata e omogenea incrementa sensibilmente l'integrità della sovrapposizione degli orbitali π tra molecole vicine, facilitando l'hopping dei portatori di carica e garantendo che elettroni e lacune possano convergere efficacemente all'interno del bulk dello strato emissivo." - } - ] - } - ], - "index": 252 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/c1e3df4eed389c56471304e53ef6eed99d2d012604f298652ded0b09061e1b5a.jpg" - } - ] - } - ], - "index": 253, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 38 - profilo energetico dell'elettroluminescenza in un polimero coniugato", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 254, - "type": "image_caption" - } - ], - "index": 253 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'interazione tra un elettrone, localizzato prevalentemente sull'unità accettrice del DPP, e una lacuna, situata sull'unità donatrice del tiofene, dà origine a uno stato eccitato transitorio definito \"eccitone\". Essendo termodinamicamente instabile, questo stato ha una vita brevissima: l'elettrone rilassa rapidamente dal livello energetico del LUMO per ricombinarsi con la lacuna nel livello HOMO. L'energia potenziale persa in questo salto energetico viene dissipata dal sistema e rilasciata verso l'esterno sotto forma di radiazione elettromagnetica, ovvero un fotone (" - }, - { - "type": "text", - "content": "Figura 38", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - }, - { - "type": "text", - "content": "45", - "style": [ - "superscript" - ] - } - ] - } - ], - "index": 255 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "È in questo istante che la progettazione macromolecolare donatore-accettore si traduce in un fenomeno ottico macroscopico: l'entità del band gap corrisponde approssimativamente all'energia del fotone emesso (" - }, - { - "type": "inline_equation", - "content": "E=h\\nu" - }, - { - "type": "text", - "content": "). Conseguentemente, il controllo chimico della struttura polimerica consente di governare in modo assoluto la lunghezza d'onda, l'intensità e il colore della luce prodotta dal dispositivo OLED, rendendo materiali complessi come il copolimero DPP-3HT dei possibili candidati per la prossima generazione di display flessibili e sorgenti di illuminazione a stato solido." - } - ] - } - ], - "index": 256 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Scopo ", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 257, - "anchor": "_Toc242438072", - "is_numbered_style": true, - "level": 1, - "section_number": "2" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il seguente progetto di tesi magistrale in Chimica Industriale è stato svolto all'interno di un gruppo di ricerca dell'Università di Bologna specializzato nella sintesi di materiali polimerici ingegnerizzati, con particolare riguardo verso le applicazioni nel campo della soft optoelectronics. Quest'ultima è una branca interdisciplinare che mira a combinare tecnologie di emissione e rilevamento della luce con dispositivi flessibili e adattabili, ideali per interfacce interattive, robotica biomimetica e sensori indossabili per il monitoraggio della salute." - } - ] - } - ], - "index": 258 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Si tratta di un campo di ricerca con numerose possibilità di innovazione, caratterizzato tuttavia dall'impiego di materiali semiconduttori π-coniugati che spesso perdono le loro proprietà ottiche allo stato solido. I principali problemi derivano infatti dalla natura altamente planare del loro scheletro molecolare, la quale induce il fenomeno noto come Aggregation-Caused Quenching (ACQ). Questo è causato dalle forti interazioni di π-stacking tra le catene polimeriche adiacenti, che smorzano drasticamente la fluorescenza del materiale limitandone le applicazioni pratiche." - } - ] - } - ], - "index": 259 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Per questo motivo, il progetto di tesi si pone come obiettivo lo sviluppo di nuovi semiconduttori" - } - ] - } - ], - "index": 260 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "polimerici emissivi in grado di superare le limitazioni imposte dall'ACQ, attraverso una strategia di design macromolecolare mirata all'ottenimento di architetture polimeriche a spazzola (bottle brush copolymers). L'intento è quello di promuovere la separazione fisica dei segmenti planari coniugati, ripristinando ed esaltando le proprietà emissive allo stato solido pur preservando l'integrità elettrochimica e la stabilità del sistema." - } - ] - } - ], - "index": 261 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Per fare ciò è stato scelto di utilizzare monomeri ortogonali a base di dichetopirrolopirrolo (DPP), una classe di molecole eteroaromatiche selezionata per le eccellenti proprietà fotofisiche. La reattività del monomero permette di far avvenire meccanismi di polimerizzazione indipendenti. In questa tesi è stata sviluppata una procedura sintetica che prevede inizialmente una condensazione pseudo-Stobbe per ottenere un fluoroforo contenente unità tiofeniche. Successivamente, attraverso l'N-alchilazione del core DPP impiegando una catena alchilica funzionalizzata con gruppi idrossilici, si è ottenuto un monomero in grado di subire due processi di polimerizzazione distinti. Sulla base di questa struttura, è stato deciso di sintetizzare inizialmente uno scheletro semiconduttore mediante copolimerizzazione ossidativa, con Fe(III) come ossidante stochiometrico, del monomero DPP con il 3-esiltiofene (3HT). La distribuzione statistica dei monomeri lungo la catena aumenta l'entropia conformazionale del sistema: ciò limita il packing molecolare e l'ordine costituzionale del polimero, una caratteristica di interesse in quanto riduce l'aggregazione delle catene principali e rende i gruppi idrossilici maggiormente accessibili per i successivi processi di funzionalizzazione." - } - ] - } - ], - "index": 262 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I materiali ottenuti sono stati infine strutturati e modificati per massimizzare l'emissione luminosa allo stato solido. Sfruttando i gruppi ossidrilici pendenti come iniziatori, è stata condotta una polimerizzazione ad apertura di anello (ROP) dell’ε-caprolattone. La crescita delle catene laterali di poli(ε-caprolattone) (PCL) ha permesso di ottenere la desiderata architettura bottle brush, favorendo la separazione sterica dei segmenti coniugati. Le proprietà foto-fisiche, termiche ed elettrochimiche di questi materiali sono state studiate per via spettroscopica (NMR, UV-Vis) e termica (DSC) e correlate con i parametri strutturali (come il peso molecolare del PCL) al fine di ottimizzarne l'emissione." - } - ] - } - ], - "index": 263 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Inoltre, per poter indagare approfonditamente l'aspetto semiconduttore dei materiali sintetizzati, tutti i polimeri sono stati caratterizzati mediante ciclovoltametria. Questa indagine elettrochimica ha permesso di confermare il mantenimento delle proprietà conduttive del core coniugato e di valutarne la stabilità ai processi di ossidoriduzione anche in seguito all'accrescimento delle catene laterali." - } - ] - } - ], - "index": 264 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Procedure sperimentali ", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 265, - "anchor": "_Toc242438073", - "is_numbered_style": true, - "level": 1, - "section_number": "3" - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Materiali e metodi ", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 266, - "anchor": "_Toc242438074", - "is_numbered_style": true, - "level": 2, - "section_number": "3.1" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Solventi e reagenti ", - "style": [ - "underline" - ] - } - ] - } - ], - "index": 267 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le reazioni riportate sono state eseguite impiegando reagenti e solventi commerciali ad elevato grado di purezza, utilizzati senza ulteriori purificazioni ad eccezione di quelli menzionati di seguito. Il CHCl" - }, - { - "type": "text", - "content": "3", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": " è stato precedentemente anidrificato per distillazione in apparato Claisen con calcio idruro come anidrificante, e il THF purificato a pressione ridotta tramite evaporatore rotante per rimuovere lo stabilizzante." - } - ] - } - ], - "index": 268 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Strumenti di caratterizzazione ", - "style": [ - "underline" - ] - } - ] - } - ], - "index": 269 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La struttura molecolare dei composti sintetizzati è stata determinata mediante l’acquisizione di spettri " - }, - { - "type": "text", - "content": "1", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "H-NMR in soluzione, effettuati con uno spettrometro “Varian Mercury 400” (400 MHz) con TMS come standard interno." - } - ] - } - ], - "index": 270 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I prodotti sono stati caratterizzati per spettroscopia infrarossa a riflettanza totale attenuata mediante uno spettrofotometro ATR-IR Bruker alpha I." - } - ] - } - ], - "index": 271 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I polimeri ottenuti sono stati caratterizzati per Gel Permeation Cromatography (GPC) in modo da determinare i loro pesi molecolari. Le analisi sono state effettuate impiegando una colonna del tipo 5MXL da 300 mm in grado di analizzare un range di Mw compreso tra 800-30000 Da. Lo strumento impiega un detector ad indice di rifrazione. I campioni sono stati solubilizzati in THF e l’analisi è stata eseguita con una velocità di flusso di 1 mL/min ad una temperatura di 20°C. La calibrazione della colonna è stata effettuata mediante standard monodispersi di polistirene." - } - ] - } - ], - "index": 272 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le analisi UV-VIS sono state eseguite con uno spettrofotometro a doppio raggio “Agilent Cary 3500 UV-Vis” acquisendo uno spettro da 800 a 200 nm usando cuvette di quarzo con un cammino ottico di 1 cm." - } - ] - } - ], - "index": 273 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le misure di fluorescenza sono state svolte con uno spettrometro Agilent Cary Eclipse, avente come sorgente una lampada allo xenon (80 Hz) e come detector un fotomoltiplicatore PMT 900." - } - ] - } - ], - "index": 274 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le transizioni termiche dei polimeri sintetizzati sono state determinate mediante Calorimetria Differenziale a Scansione (DSC) con strumento “TA Q2000” operante in atmosfera inerte di azoto e utilizzando due cicli di riscaldamento da -50°C a 250°C a 20 °C/min, intervallati da un ciclo di raffreddamento da 250°C a -50°C a -10 °C/min." - } - ] - } - ], - "index": 275 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Sintesi e procedure", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 276, - "anchor": "_Toc242438075", - "is_numbered_style": true, - "level": 2, - "section_number": "3.2" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Sintesi di 3,6-di(tiofen-2-il)-2,5-diidropirrolo[3,4-c]pirrolo-1,4-dione (1)", - "style": [ - "bold", - "italic" - ] - } - ] - } - ], - "index": 277 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 278, - "type": "image_body" - } - ], - "index": 278 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In un pallone a tre colli da 25 mL con ancoretta magnetica e refrigerante si aggiungono sotto flusso di azoto: 475 mg (20,7 mmol, 3,5 eq) di Na" - }, - { - "type": "text", - "content": "(s)", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ", 12 mL (109,7 mmol, 16,6 eq) di alcol tert-amilico (t-AmOH) e FeCl" - }, - { - "type": "text", - "content": "3", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": " in quantità catalitica. La soluzione viene scaldata a 80 °C mediante bagno d’olio e mantenuta sotto agitazione per favore la dissoluzione del sodio. Una volta solubilizzato, si aggiungono goccia a goccia 1,9 mL (20 mmol, 3eq) di 2-cianotiofene (2-CNTh) e si alza la temperatura fino a 110 °C." - } - ] - } - ], - "index": 279 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Successivamente, si sgocciolano 1,36 mL di diisopropil succinato (6,66 mmol, 1,13 eq) e si lascia reagire la soluzione per 16h." - } - ] - } - ], - "index": 280 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Si spegne la reazione lasciandola raffreddare e aggiungendo acido acetico diluito in acqua (rapporto 1:9 V/V). Il grezzo viene filtrato su imbuto buchner e lavato ripetutamente con acqua distillata e metanolo. Il prodotto ottenuta viene posto in stufa a 85 °C per eliminare eventuali tracce di acqua." - } - ] - } - ], - "index": 281 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il prodotto " - }, - { - "type": "text", - "content": "1", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " si presenta come un solido rosso scuro/violaceo." - } - ] - } - ], - "index": 282 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Caratterizzazione del prodotto ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "1", - "style": [ - "bold", - "italic" - ] - } - ] - } - ], - "index": 283 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "1", - "style": [ - "bold", - "superscript" - ] - }, - { - "type": "text", - "content": "H NMR ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "(400 MHz, d" - }, - { - "type": "text", - "content": "6", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "-DMSO): δ = 8.24 – 8.18 (dd, " - }, - { - "type": "text", - "content": "J", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": " = 3.8, 1.2 Hz, 4H), 8.00 – 7.93 (dd, " - }, - { - "type": "text", - "content": "J", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": " = 5.0, 1.1 Hz, 4H), 7.38 – 7.25 (m, 4H)" - } - ] - } - ], - "index": 284 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "UV-Vis", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " (in THF): 532 nm, 498 nm" - } - ] - } - ], - "index": 285 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Fluorescenza", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " (in THF): 490 nm" - } - ] - } - ], - "index": 286 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Sintesi del 2,5-bis(6-idrossiesil)-3,6-di(tiofen-2-il)-2,5-diidropirrolo[3,4-c]pirrolo-1,4-dione (2)", - "style": [ - "bold", - "italic" - ] - } - ] - } - ], - "index": 287 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 288, - "type": "image_body" - } - ], - "index": 288 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In un pallone a 3 colli da 50 mL dotato di ancoretta magnetica e refrigerante si aggiungono: 1 g (3,32 mmol, 1 eq) di DPP (" - }, - { - "type": "text", - "content": "1", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") e 18,75 mL (6,25 mL/mmol di DPP) di dimetilsolfossido (DMSO). Il sistema viene inertizzato mediante cicli vuoto/azoto. Successivamente, si aggiungono 1,1 g (0,01 mol, 3 eq) di tert-butossido di potassio (t-BuOK) e la miscela di reazione scaldata a 40 °C. Dopo 10 min si sgocciolano all’interno 1,08 mL (8,3 mmol, 1,25 eq) di 6-bromoesanolo e si lascia reagire per 16 h." - } - ] - } - ], - "index": 289 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Al termine della reazione si trasferisce il grezzo di reazione in un imbuto separatore da 250 mL con 100 ml di DCM. Si lava la fase organica tre volte con 100 mL di soluzione satura di KCl in acqua. La fase organica viene anidrificata con sodio solfato (Na" - }, - { - "type": "text", - "content": "2", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "SO" - }, - { - "type": "text", - "content": "4", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "), filtrata su filtro a pieghe e evaporata tramite rotavapor." - } - ] - } - ], - "index": 290 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il grezzo di reazione viene purificato mediante cristallizzazione in etanolo: il solido viene sciolto a caldo nella minima quantità di solvente e la soluzione ottenuta si ripone in freezer a -20 °C per 24 h. Al termine, si osserva nel pallone la formazione di un precipitato scuro costituito dal prodotto desiderato, il DPP bis-alchilato (" - }, - { - "type": "text", - "content": "2", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "). Il composto cristallizzato viene posto in stufa a 85 °C fino a completa eliminazione delle tracce residue di solvente." - } - ] - } - ], - "index": 291 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Caratterizzazione del prodotto ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "2", - "style": [ - "bold", - "italic" - ] - } - ] - } - ], - "index": 292 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "1", - "style": [ - "bold", - "superscript" - ] - }, - { - "type": "text", - "content": "H NMR ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "(400 MHz, CDCl" - }, - { - "type": "text", - "content": "3", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "): δ 8.96 – 8.84 (m, 1H), 7.67 – 7.58 (m, 1H), 7.33 – 7.19 (m, 2H), 4.17 – 4.04 (m, 2H), 3.73 – 3.59 (t, " - }, - { - "type": "text", - "content": "J", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": " = 6.4 Hz, 2H), 1.82 – 1.20 (m, 9H)" - } - ] - } - ], - "index": 293 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "IR", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " (ATR): 3350, 3070, 2920, 2850, 1645, 1555, 1495, 1440, 1390, 820, 730 cm⁻¹" - } - ] - } - ], - "index": 294 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "UV-Vis", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " (in THF): 541 nm" - } - ] - } - ], - "index": 295 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Fluorescenza", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " (in THF): 540 nm" - } - ] - } - ], - "index": 296 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Sintesi dei copolimeri coniugati (3a, 3b, 3c)", - "style": [ - "bold", - "italic" - ] - } - ] - } - ], - "index": 297 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 298, - "type": "image_body" - } - ], - "index": 298 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Sono stati sintetizzati tre copolimeri in base alla percentuale di DPP utilizzata (" - }, - { - "type": "text", - "content": "Tabella 3", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 299 - }, - { - "type": "table", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tabella 3 - composizione dei copolimeri", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 300, - "type": "table_caption" - }, - { - "lines": [ - { - "spans": [ - { - "type": "table", - "html": "

Copolimero

DPP (mmol)

DPP (eq)

3HT (mmol)

3HT (eq)

3a

0.2

0.2

0.8

0.8

3b

0.5

0.5

0.5

0.5

3c

0.8

0.8

0.2

0.2

" - } - ] - } - ], - "index": 301, - "type": "table_body" - } - ], - "index": 301 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La procedura sperimentale risulta analoga per ognuno dei copolimeri sintetizzati. In un pallone a tre colli posto in atmosfera d’azoto, vengono aggiunti 40 mL di cloroformio anidro (CHCl" - }, - { - "type": "text", - "content": "3", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ") ed i due monomeri nelle proporzioni corrette. La completa solubilizzazione del prodotto " - }, - { - "type": "text", - "content": "2 ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "viene favorita mediante sonicatore. In parallelo, si prepara una soluzione di 818 mg di tricloruro ferrico (FeCl" - }, - { - "type": "text", - "content": "3", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ") (5.05 mmol, 5 eq) in 10 mL di nitrometano (CH" - }, - { - "type": "text", - "content": "3", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "NO" - }, - { - "type": "text", - "content": "2", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "), lasciandola anch'essa in sonicatore per alcuni minuti per agevolarne la dissoluzione. La soluzione ossidante viene sgocciolata nel pallone mantenendo il sistema in agitazione per 1 h. Al termine, si aggiungono 30 mL di THF sbiancato e si lascia nuovamente in agitazione per 30 min." - } - ] - } - ], - "index": 302 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Successivamente, si trasferisce il grezzo di reazione in imbuto separatore e si lava con HCl 0.6 M finché la fase acquosa sottoposta al saggio con tiocianato non risulta trasparente (la persistenza del colore rosso indica la presenza di tracce residue di tricloruro ferrico; il test si esegue a partire dal terzo lavaggio). La fase organica viene estratta con una soluzione satura di NaCl in acqua, anidrificata e evaporata mediante rotavapor. Per separare il polimero dai possibili sottoprodotti (poli-3esiltiofene) e dalle molecole a basso peso molecolare viene effettuata una precipitazione in non-solvente. Il prodotto viene solubilizzato nella minima quantità di THF e si fa gocciolare in 150 mL di metanolo freddo. Il precipitato viene filtrato e la soluzione portata a secco mediante l’utilizzo del rotavapor." - } - ] - } - ], - "index": 303 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Sintesi dei polimeri bottle brush ", - "style": [ - "bold", - "italic" - ] - } - ] - } - ], - "index": 304 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 305, - "type": "image_body" - } - ], - "index": 305 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "A partire dai campioni " - }, - { - "type": "text", - "content": "3b", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " e " - }, - { - "type": "text", - "content": "3c", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " sono stati realizzati copolimeri con struttura bottle-brush a diverso peso molecolare. La quantità di " - }, - { - "type": "inline_equation", - "content": "\\varepsilon" - }, - { - "type": "text", - "content": "-caprolattone necessaria per l'innesto dei blocchi di PCL è stata determinata impostando il rapporto stechiometrico in funzione degli equivalenti di gruppi -OH del derivato DPP, considerandoli come iniziatori attivi per la ROP." - } - ] - } - ], - "index": 306 - }, - { - "type": "table", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tabella 4 - composizione dei polimeri bottle brush ", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 307, - "type": "table_caption" - }, - { - "lines": [ - { - "spans": [ - { - "type": "table", - "html": "

Copolimero

Mn teorico

Caprolattone

V (ml)

mol

3b

1500 Da (3.1b)

1.06

0.01

5000 Da (3.2b)

4.65

0.04

10000 Da (3.3b)

9.29

0.09

3c

1500 Da (3.1c)

1.72

0.02

5000 Da (3.2c)

7.43

0.07

10000 Da (3.3c)

14.87

0.1

" - } - ] - } - ], - "index": 308, - "type": "table_body" - } - ], - "index": 308 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La procedura sintetica adottata è risultata analoga per tutti i polimeri descritti in " - }, - { - "type": "text", - "content": "Tabella 4", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ". All'interno di un pallone da 30 mL dotato di rubinetto è stato introdotto il copolimero (nei quantitativi indicati in " - }, - { - "type": "text", - "content": "Tabella 4) ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "sciolto in THF. Il sistema è stato riscaldato mediante bagno ad olio siliconico ed il solvente è stato rimosso a pressione ridotta utilizzando una pompa a membrana. Ottenuto un residuo secco, il pallone è stato posto in atmosfera inerte di azoto. Sono stati quindi aggiunti 2 mL di toluene e la quantità di caprolattone indicata in " - }, - { - "type": "text", - "content": "Tabella 4", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ". La soluzione è stata portata alla temperatura di 110 °C, e successivamente, è stato aggiunto Sn(Oct)" - }, - { - "type": "text", - "content": "2", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": " in quantità catalitica. La miscela di reazione è stata mantenuta a reflusso per 24 h. Il prodotto è stato purificato mediante precipitazione in non-solvente usando metanolo freddo. Infine, il polimero precipitato è stato recuperato tramite filtrazione su imbuto Büchner ed essiccato all'aria sotto cappa aspirante in modo da allontanare ogni eventuale traccia di solvente residuo." - } - ] - } - ], - "index": 309 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Principi teorici della ciclovoltammetria ", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 310, - "anchor": "_Toc242438076", - "is_numbered_style": true, - "level": 2, - "section_number": "3.3" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "A differenza delle tecniche in stato stazionario, la CV prevede un'impostazione dinamica in cui il potenziale applicato varia in modo continuo nel tempo, rendendola uno strumento di indagine estremamente utile per caratterizzare i meccanismi di trasferimento elettronico." - } - ] - } - ], - "index": 311 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Per misurare accuratamente sia il potenziale che la corrente, l'analisi viene tipicamente condotta in una cella elettrochimica a tre elettrodi, controllata da un potenziostato. Il sistema comprende l'elettrodo di lavoro (Working Electrode, WE), ovvero la superficie su cui avviene la reazione di interesse, l'ossidazione o la riduzione della molecola (o in questo caso polimero) in esame. Il secondo componente è l'elettrodo di riferimento (Reference Electrode, RE), che possiede un potenziale noto e termodinamicamente stabile, come ad esempio un elettrodo ad Ag/AgCl o un filo di argento impiegato come pseudo-riferimento. Il potenziostato è progettato con un'impedenza d'ingresso molto elevata affinché attraverso questo elettrodo non passi alcuna corrente; in questo modo se ne impedisce la polarizzazione, garantendo che il potenziale di riferimento rimanga costante durante tutta l'analisi. Il circuito viene infine chiuso dal controelettrodo (Counter Electrode, CE), che è generalmente costituito da un materiale inerte dotato di un'ampia area superficiale, come un filo di platino. Il compito del controelettrodo è quello di permettere il passaggio della corrente necessaria a bilanciare la reazione faradica che si sviluppa sull'elettrodo di lavoro." - } - ] - } - ], - "index": 312 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il principio fondamentale della tecnica consiste nell'imporre all'elettrodo di lavoro un potenziale che varia linearmente nel tempo secondo un'onda triangolare. Il potenziale viene scansionato da un valore iniziale (" - }, - { - "type": "inline_equation", - "content": "E_{i}" - }, - { - "type": "text", - "content": ") a un valore finale o di inversione (" - }, - { - "type": "inline_equation", - "content": "E_{\\lambda }" - }, - { - "type": "text", - "content": ") con una velocità di scansione costante (scan rate, V/s), per poi invertire il senso della scansione e ritornare alle condizioni di partenza. La corrente misurata durante il ciclo rappresenta la somma di due contributi distinti: una corrente capacitiva, dovuta ai processi di carica e scarica del doppio strato elettrico all'interfaccia elettrodo/soluzione, e una corrente faradica, derivante dal reale trasferimento di elettroni tra l'elettrodo e la specie elettroattiva, descritto dalla legge di Faraday. Per minimizzare la caduta ohmica della soluzione e sopprimere la migrazione delle specie cariche per effetto del campo elettrico, l'analisi viene condotta in presenza di un elettrolita di supporto. In queste condizioni ottimali, il movimento delle specie elettroattive verso e dall'elettrodo è governato quasi esclusivamente dalla diffusione, a sua volta generata dal gradiente di concentrazione.\nIn un tipico processo redox reversibile, all’avvicinarsi del potenziale applicato a quello del potenziale standard di riduzione (E" - }, - { - "type": "text", - "content": "0", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ") della specie in esame, la corrente faradica inizia ad aumentare, seguendo il comportamento predetto dall'equazione di Nernst per l'equilibrio superficiale (" - }, - { - "type": "text", - "content": "Equazione 6", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 313 - }, - { - "type": "interline_equation", - "lines": [ - { - "spans": [ - { - "type": "interline_equation", - "content": "E=E^{0}+\\frac{RT}{nF}ln\\left(\\frac{C_{ox}}{C_{red}}\\right)" - } - ] - } - ], - "index": 314 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Equazione 6 - equazione di Nernst", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 315 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Questa corrente continua a crescere fino a raggiungere un " - }, - { - "type": "text", - "content": "p", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "icco massimo, definito corrente di picco (Ip). La formazione di tale picco si verifica poiché lo strato di soluzione immediatamente adiacente all'elettrodo si impoverisce rapidamente della specie reagente, rendendo il processo limitato dalla velocità di diffusione del materiale dal bulk della soluzione. Subito dopo il superamento del picco, lo strato di diffusione si espande verso l'interno della soluzione attenuando il gradiente di concentrazione, e conseguentemente la corrente decresce proporzionalmente a t" - }, - { - "type": "text", - "content": "-1/2", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ", seguendo l'equazione di Cottrell (" - }, - { - "type": "text", - "content": "Equazione 7", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") dove " - }, - { - "type": "inline_equation", - "content": "I\\left(t\\right)" - }, - { - "type": "text", - "content": " è la corrente al tem" - }, - { - "type": "text", - "content": "p", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "o " - }, - { - "type": "inline_equation", - "content": "t" - }, - { - "type": "text", - "content": ", " - }, - { - "type": "inline_equation", - "content": "n" - }, - { - "type": "text", - "content": " è il numero di elettroni scambiati, " - }, - { - "type": "inline_equation", - "content": "F" - }, - { - "type": "text", - "content": " è la costante di Faraday, " - }, - { - "type": "inline_equation", - "content": "A" - }, - { - "type": "text", - "content": " ra" - }, - { - "type": "text", - "content": "p", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "presenta l'area attiva dell'elettrodo, " - }, - { - "type": "inline_equation", - "content": "D" - }, - { - "type": "text", - "content": " è il coefficiente di diffusione della s" - }, - { - "type": "text", - "content": "p", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "ecie elettroattiva, " - }, - { - "type": "inline_equation", - "content": "C^{*}" - }, - { - "type": "text", - "content": " è la concentrazione della s" - }, - { - "type": "text", - "content": "p", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "ecie reagente nel bulk della soluzione e " - }, - { - "type": "inline_equation", - "content": "t" - }, - { - "type": "text", - "content": " è il tem" - }, - { - "type": "text", - "content": "p", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "o." - } - ] - } - ], - "index": 316 - }, - { - "type": "interline_equation", - "lines": [ - { - "spans": [ - { - "type": "interline_equation", - "content": "I\\left(t\\right)=\\frac{nFAD^{1/2}C^{*}}{\\pi ^{1/2}t^{1/2}}" - } - ] - } - ], - "index": 317 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Equazione 7 - equazione di Cottrell", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 318 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Invertendo poi il potenziale applicato, le specie generate all'elettrodo durante la scansione di andata subiscono il processo inverso, originando nel voltammogramma un picco di corrente di segno opposto." - } - ] - } - ], - "index": 319 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Per un sistema diffusivo ideale e reversibile, il valore della corrente di picco in funzione della velocità di scansione è descritto quantitativamente dall'equazione di Randles-Sevcik (" - }, - { - "type": "text", - "content": "Equazione 8", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "):" - } - ] - } - ], - "index": 320 - }, - { - "type": "interline_equation", - "lines": [ - { - "spans": [ - { - "type": "interline_equation", - "content": "I_{p}=\\left(2.69\\times 10^{5}\\right)\\cdot n^{3/2}\\cdot A\\cdot D^{1/2}\\cdot C\\cdot v^{1/2}" - } - ] - } - ], - "index": 321 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Equazione 8 - equazione di Randles-Sevcik", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 322 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In questa equazione, " - }, - { - "type": "inline_equation", - "content": "n" - }, - { - "type": "text", - "content": " rappresenta il numero di elettroni scambiati nella reazione redox, " - }, - { - "type": "inline_equation", - "content": "A" - }, - { - "type": "text", - "content": " è l'area attiva dell'elettrodo (cm" - }, - { - "type": "text", - "content": "2", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "), " - }, - { - "type": "inline_equation", - "content": "D" - }, - { - "type": "text", - "content": " indica il coefficiente di diffusione della specie elettroattiva (cm²/s), " - }, - { - "type": "inline_equation", - "content": "C" - }, - { - "type": "text", - "content": " è la concentrazione della specie nel bulk della soluzione (mol/cm³) e " - }, - { - "type": "inline_equation", - "content": "v" - }, - { - "type": "text", - "content": " è la velocità di scansione (V/s, " - }, - { - "type": "text", - "content": "2", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "5 °C). La proporzionalità lineare tra la corrente di picco " - }, - { - "type": "inline_equation", - "content": "I_{p}" - }, - { - "type": "text", - "content": " e la radice quadrata dello scan rate (" - }, - { - "type": "inline_equation", - "content": "v^{1/2}" - }, - { - "type": "text", - "content": ") costituisce il criterio per confermare che il processo redox in esame è effettivamente controllato dal trasporto di materia per diffusione." - } - ] - } - ], - "index": 323 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Procedure sperimentali delle analisi voltammetriche", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 324, - "anchor": "_Toc242438077", - "is_numbered_style": true, - "level": 2, - "section_number": "3.4" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le caratterizzazioni elettrochimiche sono state condotte a temperatura ambiente impiegando un potenziostato CHI660C (CH Instruments), interfacciato con una cella elettrochimica standard a tre elettrodi. Il sistema era costituito da un elettrodo di lavoro in glassy carbon (carbonio vetroso), un elettrodo di riferimento ad Ag/AgCl e un controelettrodo costituito da un filo di platino." - } - ] - } - ], - "index": 325 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tutte le misurazioni sono state eseguite in fase omogenea, utilizzando tetraidrofurano (THF) come solvente. Come elettrolita di supporto è stato impiegato il tetrabutilammonio esafluorofosfato (TBAPF" - }, - { - "type": "text", - "content": "6", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ") ad una concentrazione di 0.1 M. Prima di procedere all'analisi dei materiali sintetizzati, è stata registrata la ciclovoltammetria del bianco sulla sola soluzione elettrolitica, al fine di verificare la pulizia del sistema e l'assenza di specie elettroattive interferenti all'interno della finestra di potenziale indagata. Successivamente, la soluzione è stata utilizzata per la preparazione delle soluzioni polimeriche a una concentrazione fissa di 10 mg/mL." - } - ] - } - ], - "index": 326 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/c9be0696a5ce4170a10898c5a8c55cd66b66323a81d276c8dd911fe7631ebaf6.jpg" - } - ] - } - ], - "index": 327, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 39 - schema della cella elettrochimica impiegata nelle misure voltammetriche", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 328, - "type": "image_caption" - } - ], - "index": 327 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Inizialmente la soluzione è stata sottoposta a degasaggio tramite gorgogliamento di azoto, per rimuovere tutto l’ossigeno disciolto che potrebbe interferire con le analisi riducendosi al catodo. Successivamente, il flusso di azoto dentro la soluzione è stato rimosso per evitare perturbazioni meccaniche all’interfaccia elettrodo/soluzione durante le misure, mantenendolo solo come battente per impedire l’ingresso di ossigeno nella cella." - } - ] - } - ], - "index": 329 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le scansioni voltammetriche di base per l'identificazione dei processi redox sono state registrate applicando una velocità di scansione di 0.05 V/s, variando in seguito le velocità di scansione (0.05, 0.1, 0.5 e 1.0 V/s) per investigare l’influenza della cinetica di trasferimento. Al termine delle misurazioni per ciascun campione, è stata aggiunta una piccola quantità di ferrocene direttamente nella cella elettrochimica per fungere da standard redox interno, in quanto i potenziali misurati sperimentalmente sono relativi e strettamente dipendenti dal particolare elettrodo di riferimento impiegato. Sfruttando il comportamento reversibile e il potenziale noto della coppia redox Fc/Fc" - }, - { - "type": "text", - "content": "+", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ", è stato possibile calibrare l'asse dei potenziali e riferire i valori di onset sperimentali alla scala assoluta delle energie nel vuoto, passaggio indispensabile per un calcolo rigoroso dei livelli energetici HOMO e LUMO dei materiali." - }, - { - "type": "text", - "content": "50", - "style": [ - "superscript" - ] - } - ] - } - ], - "index": 330 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Discussione dei risultati ", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 331, - "anchor": "_Toc242438078", - "is_numbered_style": true, - "level": 1, - "section_number": "4" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In seguito, verranno discussi i dati ottenuti durante il lavoro di tesi, attraverso l’analisi critica dei risultati delle varie sintesi e delle caratterizzazioni dei diversi prodotti con l’obiettivo di comparare i dati di questo lavoro di tesi con quelli già presenti in letteratura e delineare eventuali problemi riscontrati e possibili soluzioni." - } - ] - } - ], - "index": 332 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "4.1. Dichetopirrolopirroli ", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 333, - "anchor": "_Toc242438079", - "is_numbered_style": false, - "level": 2 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il gruppo di ricerca all’interno del quale è stato svolto il lavoro di tesi si è precedentemente concentrato nella sintesi e caratterizzazione di fluorofori di natura dichetopirrolopirrolica. In particolare, è stato studiato l’effetto della presenza di gruppi funzionali elettron-attrattori (EWG) ed elettron-donatori (EDG), in posizione para sull’anello benzonitrilico, utilizzato nella formazione dei DPP, sulle proprietà foto-fisiche del fluoroforo finale (" - }, - { - "type": "text", - "content": "Figura 40", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 334 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/06ea4ef401c2c94d92ce5ebdcab91b4639e8c1827ec33f15d85a9993333b8849.png" - } - ] - } - ], - "index": 335, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 40 - sostituenti del DPP precedentemente studiati dal gruppo di ricerca", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 336, - "type": "image_caption" - } - ], - "index": 335 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L’impiego di benzonitrili con sostituenti in " - }, - { - "type": "text", - "content": "para", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": " di tipo EWG porta alla formazione di sistemi altamente emissivi; al contrario, la presenza di gruppi EDG porta alla formazione di un isomero strutturale (iso-DPP) in cui la fluorescenza nel visibile risulta inibita principalmente a causa dell'attivazione di processi di rilassamento non radiativo." - } - ] - } - ], - "index": 337 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Questo studio iniziale ha garantito solide fondamenta riguardo i possibili fluorofori da utilizzare in successive reazioni di polimerizzazione, sulla base di fattori come proprietà emissive e loro reattività." - } - ] - } - ], - "index": 338 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Con lo scopo di espandere ulteriormente le potenzialità fotofisiche di questi sistemi, il presente lavoro si è concentrato sulla sintesi e caratterizzazione di fluorofori dichetopirrolopirrolici, in cui i tradizionali anelli benzenici sono stati sostituiti da nuclei tiofenici. Successivamente, è stata sviluppata una strategia di funzionalizzazione basata su reazioni di N-alchilazione dei gruppi ammidici presenti nel core eteroaromatico. Questo approccio garantisce un notevole aumento della solubilità del fluoroforo finale, offrendo al contempo una procedura sintetica semplice e scalabile." - } - ] - } - ], - "index": 339 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In " - }, - { - "type": "text", - "content": "Figura 41", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " è rappresentato lo schema di reazione del fluoroforo " - }, - { - "type": "text", - "content": "2", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", successivamente utilizzato nelle reazioni di polimerizzazione. In seguito, vengono analizzati i vari step di reazione e le rispettive caratterizzazioni." - } - ] - } - ], - "index": 340 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 341, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 41 - schema di reazione del fluoroforo 2", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 342, - "type": "image_caption" - } - ], - "index": 341 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La sintesi del composto " - }, - { - "type": "text", - "content": "1", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " è stata eseguita sulla base delle procedure sintetiche descritte in letteratura, seguendo un meccanismo di ciclizzazione di tipo pseudo-Stobbe" - }, - { - "type": "text", - "content": "5,7", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ". In particolare, viene fatto reagire il derivato tiofenico con un estere succinico, in questo caso il diisopropil succinato. La reazione richiede la presenza di una base forte per la deprotonazione dell’estere succinico in posizione α al carbonile, azione eseguita dal teramilato di sodio (t-AmONa), ottenuto mediante salificazione dell’alcol ter-amilico con sodio in presenza di una quantità catalitica di FeCl" - }, - { - "type": "text", - "content": "3", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ". Una volta formatosi il carbanione, questo attacca il carbonio nitrilico del tiofene e porta al composto imminico che tautomerizza alla corrispondente enammina. Il gruppo amminico riesce ad attaccare il carbonile estereo in modo intramolecolare, portando alla chiusura del primo anello a cinque termini. Una seconda deprotonazione, con successivo attacco di una seconda molecola di tiofene, porta alla formazione di una nuova enammina, che nuovamente attacca il carbonile estereo, portando alla chiusura del secondo anello a cinque termini con formazione della struttura dichetopirrolopirrolica. Il meccanismo descritto è riportato in " - }, - { - "type": "text", - "content": "Figura 42", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 343 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 344, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 42 - meccanismo di reazione proposto per la formazione dei DPP", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 345, - "type": "image_caption" - } - ], - "index": 344 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il tiofene è stato introdotto direttamente nell’ambiente di reazione dopo la formazione dell’alcolato, mentre il succinato è stato gocciolato lentamente all’interno del pallone in quanto una concentrazione locale troppo elevata di quest’ultimo in condizioni basiche potrebbe indurre reazioni parassite di autocondensazione (" - }, - { - "type": "text", - "content": "Figura 43", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "). In particolare, è stato scelto il diisopropil succinato per aumentare l’ingombro sterico intorno al carbonile e diminuire ulteriormente la possibilità dell’estere di subire autocondensazione di Claisen e successiva ciclizzazione, come riportato in letteratura." - }, - { - "type": "text", - "content": "7 ", - "style": [ - "superscript" - ] - } - ] - } - ], - "index": 346 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 347, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 43 - meccanismo di autocondensazione di Claisen", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 348, - "type": "image_caption" - } - ], - "index": 347 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La purificazione della reazione è stata effettuata sfruttando la netta differenza di solubilità tra i reagenti ed il prodotto della reazione; una volta isolato il DPP dall’ambiente di reazione sono stati ripetuti numerosi lavaggi con acqua e metanolo per eliminare solvente e reagenti ancora presenti." - } - ] - } - ], - "index": 349 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il prodotto, quindi, è stato sottoposto ad una serie di caratterizzazioni con lo scopo di determinarne l’effettiva struttura e proprietà fotofisiche." - } - ] - } - ], - "index": 350, - "anchor": "_Ref234848565" - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/7ee78c7f6eefe1816ac3830635c0335bfcb7376ab193625f3346fbd98ef4fe64.png" - } - ] - } - ], - "index": 351, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 44 - spettro ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "1", - "style": [ - "italic", - "superscript" - ] - }, - { - "type": "text", - "content": "H-NMR in DMSO del prodotto ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "1", - "style": [ - "bold", - "italic" - ] - } - ] - } - ], - "index": 352, - "type": "image_caption" - } - ], - "index": 351 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Lo spettro " - }, - { - "type": "text", - "content": "1", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "H-NMR del prodotto " - }, - { - "type": "text", - "content": "1", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " viene riportato in Figura 44; la presenza di elementi di simmetria rende chimicamente equivalenti diversi gruppi di protoni, riducendo così il numero di segnali distinti rispetto al totale degli atomi di idrogeno presenti." - } - ] - } - ], - "index": 353 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Nella regione a circa 11 ppm si osserva un singoletto allargato attribuibile ai due protoni ammidici appartenenti ai due anelli lattamici fusi nel core dichetopirrolopirrolico. Tale segnale risulta marcatamente deschermato per effetto dell'azione sinergica tra il forte richiamo elettronico dei gruppi carbonilici adiacenti, l'esteso sistema π-coniugato del core molecolare e l'instaurarsi di legami a idrogeno intermolecolari con il solvente. Nella regione aromatica, invece, si identificano i segnali caratteristici dei due anelli tiofenici laterali. Il doppietto maggiormente deschermato è assegnabile ai protoni fisicamente più prossimi al core dichetopirrolopirrolico. Procedendo verso campi più alti, si osserva un secondo doppietto corrispondente ai protoni adiacenti all'eteroatomo di zolfo, il cui shift chimico risente del suo noto effetto induttivo. Infine, l'ulteriore segnale, che si risolve come un doppietto di doppietti a campi ancora maggiori, è attribuibile ai protoni centrali dell'anello tiofenico, i quali subiscono accoppiamento con entrambi i protoni vicinali." - } - ] - } - ], - "index": 354 - }, - { - "type": "chart", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "chart", - "content": "
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È inoltre interessante notare uno Stokes Shift di soli 11 nm, indice del fatto che l'elevata rigidità molecolare del sistema minimizza i riarrangiamenti strutturali tra stato fondamentale ed eccitato, limitando così i decadimenti non radiativi in seguito all’eccitazione." - } - ] - } - ], - "index": 357 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Sfruttando la reattività del DPP ottenuto, descritta accuratamente nel " - }, - { - "type": "text", - "content": "Capitolo 1.1.2", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", è stata effettuata una reazione di N-alchilazione su entrambi gli azoti ammidici del DPP, utilizzando il 6-bromo-1-esanolo come agente alchilante. L’inserimento di una catena alchilica contente un gruppo ossidrilico, ha permesso di ottenere un monomero ortogonale e tetrafunzionale in grado di poter dare in maniera indipendente differenti tipi di polimerizzazione." - } - ] - } - ], - "index": 358 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La presenza degli anelli tiofenici può dare reazioni di polimerizzazione ossidativa mediante l’utilizzo stechiometrico di ferro tricloruro, mentre i gruppi ossidrilici assimilano la struttura ad un’unità monomerica di tipo diolica e per questo impiegabile nelle comuni reazioni di policondensazione con opportuni comonomeri. Inoltre, il gruppo -OH può agire da iniziatore per reazioni di tipo Ring Opening Polymerization (ROP) che coinvolgono monomeri ciclici." - } - ] - } - ], - "index": 359 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La reazione di N-alchilazione del lattame avviene mediante una tipica sostituzione nucleofila: l'azoto ammidico, deprotonato tramite l'impiego di una base forte come potassio ter-butossido (t-BuOK), agisce da nucleofilo attaccando il carbonio alifatico adiacente all'atomo di bromo (" - }, - { - "type": "text", - "content": "Figura 46", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 360 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 361, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 46 - meccanismo della reazione di N-alchilazione", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 362, - "type": "image_caption" - } - ], - "index": 361 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le condizioni operative hanno richiesto un controllo rigoroso della concentrazione della base, poiché un suo eccesso potrebbe favorire una reazione collaterale di ciclizzazione indesiderata a carico del 6-bromo-1-esanolo (" - }, - { - "type": "text", - "content": "Figura 47", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 363 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 364, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 47 - reazione di ciclizzazione del 6-bromo-1-esanolo", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 365, - "type": "image_caption" - } - ], - "index": 364 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La fase di work-up è stata condotta mediante estrazioni liquido-liquido al fine di allontanare le impurezze idrosolubili, tra cui i sali inorganici generati, gli eccessi di base ed eventuali tracce di solvente di reazione. La fase organica in DCM è stata lavata con una soluzione acquosa satura di cloruro di potassio (KCl). Dopo aver rimosso l'umidità residua trattando la fase organica con sodio solfato anidro (Na" - }, - { - "type": "text", - "content": "2", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "SO" - }, - { - "type": "text", - "content": "4", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ") e aver filtrato l'agente essiccante, il grezzo isolato è stato sottoposto al processo di purificazione." - } - ] - } - ], - "index": 366 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il prodotto è stato purificato per cristallizzazione, una tecnica che sfrutta la solubilità e capacità di cristallizzare del prodotto in uno specifico solvente, in questo caso etanolo. Sciogliendo il grezzo a caldo nella minima quantità di etanolo necessaria e inducendo successivamente una lenta precipitazione mediante prolungato raffreddamento a bassa temperatura (-20°C), è stato possibile isolare selettivamente il composto d’interesse, lasciando le impurezze maggiormente solubili nelle acque madri. Il precipitato scuro, corrispondente al DPP bis-alchilato, è infine stato recuperato mediante filtrazione. Il prodotto " - }, - { - "type": "text", - "content": "2", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " ottenuto è stato caratterizzato mediante spettroscopia NMR e FT-IR." - } - ] - } - ], - "index": 367 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/b270db169fe23b49376d4aa1759d245f0a0c16a88ce5e4bb20c7b381daed37c0.png" - } - ] - } - ], - "index": 368, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 48 - spettro ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "1", - "style": [ - "italic", - "superscript" - ] - }, - { - "type": "text", - "content": "H-NMR in CDCl", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "3", - "style": [ - "italic", - "subscript" - ] - }, - { - "type": "text", - "content": " del prodotto ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "2", - "style": [ - "bold", - "italic" - ] - } - ] - } - ], - "index": 369, - "type": "image_caption" - } - ], - "index": 368 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Nella regione aromatica dello spettro 1H-NMR, riportato in " - }, - { - "type": "text", - "content": "Figura 48", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", si osservano chiaramente tre distinti segnali assegnabili ai protoni degli anelli tiofenici. Il segnale più indicativo è rappresentato da un doppietto a campi particolarmente bassi (circa 8.9 ppm), attribuibile ai protoni fortemente deschermati per effetto dei gruppi carbonilici adiacenti del core DPP. Gli altri due protoni tiofenici completano il pattern generando gli altri due segnali separati a campi progressivamente più alti (7.6 ppm e 7.3 ppm). L'avvenuta reazione di N-alchilazione è comprovata, nella regione alifatica, dalla comparsa di due multipletti: il segnale più deschermato (4.1 ppm) è relativo ai gruppi metilenici legati direttamente all'azoto lattamico, mentre il secondo (3.6 ppm) corrisponde ai metileni adiacenti all'ossidrile terminale. Infine, i restanti protoni metilenici della catena alifatica sono chiaramente visibili sotto forma di multipletti nella regione compresa tra 1 e 2 ppm." - } - ] - } - ], - "index": 370 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/0d8a5329d339fbc86b534f67282d254ffdea0186129f5383181c6e7cd8e71bea.png" - } - ] - } - ], - "index": 371, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 49 - spettro FT-IR del prodotto", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": " 2", - "style": [ - "bold", - "italic" - ] - } - ] - } - ], - "index": 372, - "type": "image_caption" - } - ], - "index": 371 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Dallo spettro FT-IR in " - }, - { - "type": "text", - "content": "Figura 49 ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "si possono osservare picchi coerenti con la struttura del DPP alchilato. A circa 3400 cm⁻¹ si osserva una banda larga attribuibile allo stretching del legame O-H dei gruppi alcolici terminali. I segnali deboli intorno a 3100 cm⁻¹ corrispondono allo stretching dei C-H aromatici degli anelli tiofenici, mentre i due picchi netti a 2930 e 2850 cm⁻¹ sono tipici dello stretching (asimmetrico e simmetrico) dei C-H alifatici dei gruppi metilenici. Il segnale più indicativo è la banda molto intensa a circa 1650 cm⁻¹, relativa allo stretching dei gruppi carbonilici (C=O) dei lattami in sistemi coniugati, tipica dei sistemi dichetopirrolopirrolici. Nella regione 1500-1400 cm⁻¹ compaiono gli stretching C=C degli anelli aromatici e del core. Infine, nella zona del fingerprint, sono presenti dei picchi compatibili lo stretching C-O degli alcol primari e ai bending dei C-H tiofenici." - } - ] - } - ], - "index": 373 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Per completare la caratterizzazione, il fluoroforo è stato analizzato mediante spettroscopia di assorbimento (UV-Visibile) e di emissione, in modo da poter confrontare le proprietà foto-fisiche con quelle del DPP di partenza (" - }, - { - "type": "text", - "content": "Figura 50", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 374 - }, - { - "type": "chart", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "chart", - "content": "
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", - "image_path": "" - } - ] - } - ], - "index": 375, - "type": "chart_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 50 - spettro UV-Visibile e di emissione del prodotto2 in THF", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 376, - "type": "chart_caption" - } - ], - "index": 375 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In seguito all’alchilazione si osserva uno spostamento batocromico del massimo di assorbimento, passando da 531 nm nel caso del prodotto " - }, - { - "type": "text", - "content": "1", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " a 541 nm del prodotto " - }, - { - "type": "text", - "content": "2", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ". Tale fenomeno è riconducibile all'effetto induttivo elettron-donatore delle catene alifatiche, le quali arricchiscono la densità elettronica sugli atomi di azoto determinando una destabilizzazione energetica dell'orbitale HOMO e un conseguente restringimento del bandgap ottico. Lo Stokes shift, invece, è simile per entrambi i fluorofori e vale circa 14 nm." - } - ] - } - ], - "index": 377 - }, - { - "type": "table", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tabella 5 - dati spettroscopici dei fluorofori sintetizzati", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 378, - "type": "table_caption" - }, - { - "lines": [ - { - "spans": [ - { - "type": "table", - "html": "

Prodotto

λmax, abs (nm)

λmax, ex (nm)

Stokes shift (nm)

ε (M-1 cm-1)

1

531

542

11

2800051

2

541

555

14

13218

" - } - ] - } - ], - "index": 379, - "type": "table_body" - } - ], - "index": 379 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Inoltre, è stato possibile calcolare il coefficiente di estinzione molare ε (M" - }, - { - "type": "text", - "content": "-1", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " cm" - }, - { - "type": "text", - "content": "-1", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ") del prodotto " - }, - { - "type": "text", - "content": "2 ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "mediante una retta di calibrazione ottenuta valutando l’assorbanza per via spettrofotometrica di diverse soluzioni di fluoroforo in cloroformio (CHCl" - }, - { - "type": "text", - "content": "3", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ") a concentrazione nota. La pendenza della curva, secondo la legge di Lambert-Beer, rappresenta graficamente la ε; il valore calcolato risulta essere di 13218 M" - }, - { - "type": "text", - "content": "-1", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " cm" - }, - { - "type": "text", - "content": "-1", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " (" - }, - { - "type": "text", - "content": "Figura 51", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 380 - }, - { - "type": "chart", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "chart", - "content": "
Concentrazione (mol/L)Series1
9.9999999999999995E-71.9810000000000001E-2
4.9999999999999996E-65.8220000000000001E-2
1.0000000000000001E-50.15620000000000001
5.0000000000000002E-50.66590000000000005
", - "image_path": "" - } - ] - } - ], - "index": 381, - "type": "chart_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 51 - retta di calibrazione del fluoroforo ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "2", - "style": [ - "bold", - "italic" - ] - }, - { - "type": "text", - "content": " per il calcolo di ε", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 382, - "type": "chart_caption" - } - ], - "index": 381 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "4.2. Copolimeri coniugati ", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 383, - "anchor": "_Toc242438080", - "is_numbered_style": false, - "level": 2 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Successivamente alla sintesi e alla caratterizzazione fotofisica del fluoroforo dichetopirrolopirrolico " - }, - { - "type": "text", - "content": "2", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", l'attenzione è stata rivolta alla sua integrazione in sistemi polimerici coniugati. In tale ottica, si è proceduto alla sintesi di copolimeri statistici, facendo reagire questo monomero con il 3-esiltiofene (3HT)." - } - ] - } - ], - "index": 384 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La scelta del 3HT come comonomero è stata guidata dalla collaborazione con il gruppo di ricerca del Prof. Lanzi. L'esperienza pregressa di tale gruppo ha infatti ampiamente convalidato l'efficacia e la versatilità della polimerizzazione ossidativa applicata a questa classe di derivati tiofenici. La scelta di questa specifica via sintetica, inoltre, si giustifica alla luce di diversi vantaggi operativi: a differenza dei tradizionali e più complessi metodi di " - }, - { - "type": "text", - "content": "cross-coupling", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": " catalizzati da metalli di transizione, la polimerizzazione ossidativa diretta non richiede la pre-funzionalizzazione dei monomeri, diminuendo drasticamente gli step sintetici. Inoltre, richiedendo condizioni termodinamiche blande, temperatura ambiente e pressione atmosferica, il processo si distingue per una notevole semplicità esecutivo ed un basso costo energetico. Tali caratteristiche le conferiscono un grande potenziale di scale-up, aspetto di notevole rilevanza nell’ambito di ricerca di questa tesi." - } - ] - } - ], - "index": 385 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Sotto il profilo strutturale e funzionale, la selezione del 3HT è motivata dalle note proprietà elettroniche dei politiofeni, classificati in letteratura tra i più efficienti polimeri semiconduttori organici." - }, - { - "type": "text", - "content": "52 ", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "L'inserimento di questa unità nella catena polimerica persegue quindi un duplice obiettivo: da un lato, la presenza della catena esilica assicura l'aumento di solubilità del materiale finale nei comuni solventi organici, requisito fondamentale per la successiva processabilità del polimero; dall'altro lato, l'anello tiofenico contribuisce attivamente all'estensione del sistema π-coniugato, agendo in sinergia con gli altri moduli strutturali della catena per modulare il band gap del materiale e ottimizzare le prestazioni di trasporto di carica del polimero semiconduttore." - } - ] - } - ], - "index": 386 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La reazione di polimerizzazione ossidativa del fluoroforo " - }, - { - "type": "text", - "content": "2", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " con il 3HT è stata effettuata secondo lo schema di reazione riportato in " - }, - { - "type": "text", - "content": "Figura 52", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 387 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 388, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 52 - schema di reazione dei copolimeri coniugati", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 389, - "type": "image_caption" - } - ], - "index": 388 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il primo stadio del meccanismo di polimerizzazione ossidativa è governato dalla reattività del tricloruro ferrico (FeCl" - }, - { - "type": "text", - "content": "3", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "). In questo caso, il sale inorganico funge da agente ossidante ed è impiegato in eccesso stechiometrico rispetto ai reagenti. Il centro metallico Fe" - }, - { - "type": "text", - "content": "3+ ", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "promuove l'attivazione dei monomeri attraverso un processo di trasferimento mono-elettronico (Single Electron Transfer, SET)" - }, - { - "type": "text", - "content": "53", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ". Durante questa fase, il ferro estrae un elettrone dagli anelli tiofenici dei monomeri, elettron-ricchi di natura, riducendosi a Fe" - }, - { - "type": "text", - "content": "2+", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ". Questa reazione redox porta alla generazione di cationi radicalici fortemente delocalizzati sul sistema π-coniugato dei dichetopirrolopirroli e dei derivati tiofenici. Questi intermedi, altamente reattivi, rappresentano i veri centri attivi della polimerizzazione, che tendono a legarsi per formare i nuovi legami carbonio-carbonio necessari all'accrescimento della catena (" - }, - { - "type": "text", - "content": "Figura 53", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 390 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 391, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 53 - meccanismo di polimerizzazione ossidativa mediante tricloruro ferrico", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 392, - "type": "image_caption" - } - ], - "index": 391 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Per garantire l'efficienza e il controllo di questa propagazione radicalica, l'impiego del nitrometano (CH" - }, - { - "type": "text", - "content": "3", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "NO" - }, - { - "type": "text", - "content": "2", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ") all'interno della miscela di solventi risulta determinante. Allo stato solido e in solventi non coordinanti come il cloroformio, il FeCl" - }, - { - "type": "text", - "content": "3", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": " tende a formare dimeri o aggregati, nei quali i siti attivi per l'ossidazione sono limitati alla superficie o ai difetti strutturali dei cluster. L'introduzione del nitrometano nella miscela di reazione risolve questa criticità: agendo come legante, esso rompe i ponti alogeno intermolecolari, spezzando i dimeri e solvatando il cloruro ferrico. La formazione di questi complessi di coordinazione con il nitrometano attiva di fatto il sistema, generando una soluzione omogenea di centri metallici discreti e stericamente accessibili per il trasferimento elettronico. Parallelamente, la coordinazione del ferro con il nitrometano ne modera sensibilmente sia la forte acidità di Lewis che il potenziale ossidante. Questa azione attenuatrice è essenziale per indirizzare la cinetica di reazione: controllando la forza dell'ossidante, si prevengono reazioni secondarie come l'iper-ossidazione della catena o l'insorgere di difetti di reticolazione (cross-linking). Di conseguenza si migliora la regioselettività della polimerizzazione, massimizzando la regolarità strutturale e l'estensione della π-coniugazione nel copolimero semiconduttore " - }, - { - "type": "text", - "content": "3 ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "sintetizzato." - } - ] - } - ], - "index": 393 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Come solvente di reazione, invece, è stato scelto di utilizzare il cloroformio anidro, necessario per prevenire reazioni secondarie indotte dall'umidità. L'acqua, agendo come nucleofilo e base di Lewis, potrebbe interferire con il processo di polimerizzazione attraverso due meccanismi competitivi. In primo luogo, si potrebbe coordinare al FeCl" - }, - { - "type": "text", - "content": "3 ", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "formando specie idrate stabili; ciò saturerebbe la sfera di coordinazione del metallo, riducendone il potenziale ossidativo e inibendo l'innesco della reazione. In secondo luogo, l'acqua potrebbe causare il quenching degli intermedi cationico-radicalici in propagazione. Questo attacco nucleofilo porterebbe alla terminazione prematura della catena polimerica e all'introduzione di difetti strutturali, i quali interromperebbero la coniugazione della catena compromettendo le proprietà semiconduttrici del copolimero " - }, - { - "type": "text", - "content": "3", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 394 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Una volta completato il tempo di reazione, l'isolamento del materiale polimerico ha richiesto un accurato work-up, mirato non solo al recupero del prodotto, ma soprattutto alla completa rimozione delle impurità inorganiche e delle frazioni a basso peso molecolare." - } - ] - } - ], - "index": 395 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Inizialmente sono stati effettuati lavaggi con acido cloridrico, in questo modo si mantengono i sali di ferro disciolti nella fase acquosa, evitando che precipitino sotto forma di idrossidi insolubili all’interfaccia. La completa rimozione dell’ossidante inorganico è un requisito fondamentale per mantenere l’elettronica del copolimero realizzato: tracce di metalli di transizione all’interno del backbone polimerico abbatterebbero la mobilità dei portatori di carica e spegnerebbero la fluorescenza del materiale. Per monitorare l'efficacia dell'estrazione, le acque di lavaggio sono state sottoposte al saggio del tiocianato. L'aggiunta dello ione SCN" - }, - { - "type": "text", - "content": "- ", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "genera, in presenza di ioni Fe" - }, - { - "type": "text", - "content": "3+", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ", un complesso di coordinazione caratterizzato da un'intensa colorazione rossa. I lavaggi acidi sono stati ripetuti fino all'ottenimento di un saggio negativo (soluzione incolore), a riprova della totale purificazione del sistema organico dai residui inorganici." - } - ] - } - ], - "index": 396 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'ultimo lavaggio con una soluzione acquosa mezza satura di cloruro di sodio (NaCl) sfrutta l'elevata forza ionica del sale per massimizzare l'effetto di salting-out: l'ambiente acquoso salino favorisce l'estrazione dell'acqua parzialmente disciolta nel solvente organico. Questa azione di pre-anidrificazione trascina nella fase acquosa anche le ultimissime tracce di impurità idrosolubili, come l'HCl residuo, garantendo l'isolamento di una fase organica di elevata purezza." - } - ] - } - ], - "index": 397 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Dopo aver isolato e anidrificato la fase organica, e rimosso il solvente, è stata necessaria una purificazione del solido grezzo. Al fine di allontanare i sottoprodotti di sintesi, primo fra tutti l'omopolimero del 3-esiltiofene, si è ricorsi a una purificazione mediante precipitazione selettiva in un sistema solvente/non-solvente. Il grezzo di reazione è stato solubilizzato nel minor volume possibile di THF e fatto gocciolare in un ampio eccesso di metanolo freddo." - } - ] - } - ], - "index": 398 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In queste condizioni, il copolimero d'interesse mantiene un'affinità sufficiente con la miscela, rimanendo disciolto nella fase liquida. Al contrario, la frazione contenente l’omopolimero (poli-3HT) risulta insolubile nel non-solvente, portando ad una precipitazione. La fase liquida contenente il copolimero purificato, è stata infine portata a secco, permettendo di isolare il materiale d'interesse idoneo per le successive caratterizzazioni." - } - ] - } - ], - "index": 399 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Al fine di indagare la relazione struttura-proprietà e di valutare l'incidenza del core fluorescente sulle caratteristiche finali del materiale, la reazione di polimerizzazione è stata condotta variando il rapporto stechiometrico tra i due monomeri. Nello specifico, sono stati sintetizzati tre differenti copolimeri, modulando la frazione molare del derivato dichetopirrolopirrolico (" - }, - { - "type": "text", - "content": "2", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") rispetto al 3-esiltiofene (" - }, - { - "type": "text", - "content": "Tabella 6", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 400 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'obiettivo era prepare una serie di materiali per studiare l'andamento delle proprietà al variare dell'architettura macromolecolare, ipotizzando di passare da un sistema a maggioranza tiofenica fino a uno equimolare o dominato dal DPP. Tuttavia, specifiche problematiche di reazione hanno limitato l'integrazione del monomero DPP a un massimo del 35%. Tale discrepanza è riconducibile ad una differenza nei rapporti di reattività dei due comonomeri, fortemente influenzata dall'ingombro sterico del nucleo DPP. Quest'ultimo, infatti, risulta svantaggiato nell'accoppiamento rispetto al derivato tiofenico, la cui maggiore reattività e minor volume ne favoriscono l’addizione preferenziale. Si è quindi ottenuta una libreria di materiali in cui si passa da un " - }, - { - "type": "text", - "content": "backbone", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": " con minime quantità di DPP (copolimero " - }, - { - "type": "text", - "content": "3a", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), a uno in cui la sua percentuale aumenta (copolimero " - }, - { - "type": "text", - "content": "3b", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), fino a giungere al sistema maggiormente arricchito (copolimero " - }, - { - "type": "text", - "content": "3c", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), mantenendo però in tutti i casi un rapporto molare a favore delle unità di 3-esiltiofene." - } - ] - } - ], - "index": 401 - }, - { - "type": "table", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tabella 6 - composizione dei copolimeri coniugati", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 402, - "type": "table_caption" - }, - { - "lines": [ - { - "spans": [ - { - "type": "table", - "html": "

Copolimero

moli DPP 2

moli 3HT

% DPP teorica (mol/mol)

% DPP reale (mol/mol)

3a

0.2

0.8

20

25.2

3b

0.5

0.5

50

32.6

3c

0.8

0.2

80

35.3

" - } - ] - } - ], - "index": 403, - "type": "table_body" - } - ], - "index": 403 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La composizione percentuale reale delle unità di DPP all'interno dei copolimeri è stata determinata mediante spettroscopia ¹H-NMR (" - }, - { - "type": "text", - "content": "Figura 54", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", " - }, - { - "type": "text", - "content": "Figura 55", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", " - }, - { - "type": "text", - "content": "Figura 56", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "). L'analisi quantitativa si è basata sull'integrazione di due segnali: il picco relativo ai protoni del gruppo metilico (CH₃) del 3-esiltiofene e quello corrispondente ai protoni dei gruppi metilenici (CH₂) adiacenti alle funzioni idrossiliche del DPP." - } - ] - } - ], - "index": 404 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I valori delle aree ottenute sono stati normalizzati rispetto al numero di protoni magneticamente equivalenti. La percentuale molare di DPP nel copolimero è stata calcolata mediante l’" - }, - { - "type": "text", - "content": "Equazione 9", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 405 - }, - { - "type": "interline_equation", - "lines": [ - { - "spans": [ - { - "type": "interline_equation", - "content": "\\%DPP=\\frac{\\frac{A_{DPP}}{n_{DPP}}}{\\frac{A_{DPP}}{n_{DPP}}+\\frac{A_{3HT}}{n_{3HT}}}\\times 100" - } - ] - } - ], - "index": 406 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Equazione 9 - calcolo della percentuale di DPP nei copolimeri dagli spettri ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "1", - "style": [ - "italic", - "superscript" - ] - }, - { - "type": "text", - "content": "H-NMR", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 407 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "dove " - }, - { - "type": "inline_equation", - "content": "A_{DPP}" - }, - { - "type": "text", - "content": " e " - }, - { - "type": "inline_equation", - "content": "A_{3HT}" - }, - { - "type": "text", - "content": " rappresentano i valori delle aree integrate per i rispettivi segnali, mentre " - }, - { - "type": "inline_equation", - "content": "n_{DPP}" - }, - { - "type": "text", - "content": " e " - }, - { - "type": "inline_equation", - "content": "n_{3HT}" - }, - { - "type": "text", - "content": " indicano il numero di protoni magneticamente equivalenti che generano il segnale." - } - ] - } - ], - "index": 408 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La percentuale reale di DPP 2 presente nei tre copolimeri è riportata in " - }, - { - "type": "text", - "content": "Tabella 6", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 409 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/dec925e1492a9c3c3e5aa39b3529b88ec72ca6de9cd925a787cad12199f30167.png" - } - ] - } - ], - "index": 410, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 54 - Spettro ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "1", - "style": [ - "italic", - "superscript" - ] - }, - { - "type": "text", - "content": "H-NMR del copolimero 3a in CDCl", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "3", - "style": [ - "italic", - "subscript" - ] - } - ] - } - ], - "index": 411, - "type": "image_caption" - } - ], - "index": 410 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/8b16419f042a8c9093868c26dde981bbd3b916bc37d4f110d9975493fa54977f.png" - } - ] - } - ], - "index": 412, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 55 - Spettro ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "1", - "style": [ - "italic", - "superscript" - ] - }, - { - "type": "text", - "content": "H-NMR del copolimero 3b in CDCl", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "3", - "style": [ - "italic", - "subscript" - ] - } - ] - } - ], - "index": 413, - "type": "image_caption" - } - ], - "index": 412 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/d89d66a28dc9ad9520ea6c139728786591c52e8edfc43669b6b14ee5347aeece.png" - } - ] - } - ], - "index": 414, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 56 - Spettro ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "1", - "style": [ - "italic", - "superscript" - ] - }, - { - "type": "text", - "content": "H-NMR del copolimero 3c in CDCl", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "3", - "style": [ - "italic", - "subscript" - ] - } - ] - } - ], - "index": 415, - "type": "image_caption" - } - ], - "index": 414 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In seguito all’analisi strutturale effettuata tramite spettroscopia NMR, i copolimeri sintetizzati sono stati caratterizzati mediante spettroscopia FT-IR, UV-Vis e di emissione, mentre la distribuzione dei pesi molecolari e il comportamento termico sono stati valutati rispettivamente tramite Cromatografia a Permeazione di Gel (GPC) e Calorimetria a Scansione Differenziale (DSC)." - } - ] - } - ], - "index": 416 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/979f160dc1f93431a828dae823800239399ea6eb43ccdb12ebb1036bfe071e0e.png" - } - ] - } - ], - "index": 417, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 57 - spettro FT-IR dei copolimeri 3a (blu), 3b (verde), 3c (rosso)", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 418, - "type": "image_caption" - } - ], - "index": 417 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'analisi FT-IR (" - }, - { - "type": "text", - "content": "Figura 57", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") conferma l'avvenuta copolimerizzazione per i campioni " - }, - { - "type": "text", - "content": "3a", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " (traccia verde), " - }, - { - "type": "text", - "content": "3b", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " (traccia rossa) e " - }, - { - "type": "text", - "content": "3c", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " (traccia blu). Tutti gli spettri mostrano gli stretching dei legami C-H alifatici (~2920 e ~2850 cm⁻¹) e il segnale a ~820 cm⁻¹ caratteristico dell'anello del 3-esiltiofene. L'incorporazione del DPP è provata dall'intenso picco del carbonile lattamico (C=O) a ~1650 cm⁻¹ e dallo stretching C-O a ~1050 cm⁻¹. Come atteso dai dati NMR, la banda degli ossidrili terminali (3300-3400 cm⁻¹) risulta evidente nei polimeri " - }, - { - "type": "text", - "content": "3b", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " e " - }, - { - "type": "text", - "content": "3c", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", mentre a minore intensità nel " - }, - { - "type": "text", - "content": "3a", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", confermando il minor contenuto di unità DPP in quest'ultimo campione." - } - ] - } - ], - "index": 419 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La caratterizzazione foto-fisica dei copolimeri sintetizzati è stata effettuata combinando spettroscopia di assorbimento (UV-Vis) ed emissione (" - }, - { - "type": "text", - "content": "Figura 58", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", " - }, - { - "type": "text", - "content": "Figura 59", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", " - }, - { - "type": "text", - "content": "Figura 60", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 420 - }, - { - "type": "chart", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "chart", - "content": "
UV-Visibile XUV-Visibile YEmissione XEmissione Y
7004.9098937286178687E-2504.92001340000002-1.2678678855713818E-2
6995.1249626950878771E-2505.97000120000001-1.8844468957529621E-2
6985.1879430772832413E-2506.85998540000003-2.2547852759309095E-2
6975.2579595390031326E-2507.9100037-2.3138905564867859E-2
6965.2177482518068218E-2508.9500122-2.2403132047543434E-2
6955.2867257740675598E-2509.85000609999997-1.997970448167833E-2
6945.4013911143591394E-2510.89001459999997-1.6765936465308752E-2
6935.4486262934556461E-2511.94000240000003-1.2307685335295269E-2
6925.4848255319458063E-2512.97998050000001-9.3127981721869667E-3
6915.6601182305834288E-2513.88000490000002-5.6241982722040141E-3
6905.6842877855508178E-2514.919982900000042.0627448681398361E-3
6895.6863958815068193E-2515.969970699999989.081851218941641E-3
6885.7496409818110078E-2516.859985400000031.7529065971830363E-2
6875.9047288002046186E-2517.90997312.8660005490661632E-2
6866.0088711705376101E-2518.950012199999954.1216162555106871E-2
6856.1171419219237695E-2519.849975599999995.7322364533830661E-2
6846.2122294073102866E-2520.890014599999977.3660682012317152E-2
6836.2669563564611716E-2521.940002400000039.617552559992211E-2
6826.4324483197368124E-2522.979980500000010.12130649680721313
6816.5477130928567134E-2523.880004900000020.15353016751909992
6806.6900303752311083E-2524.919982900000040.17794141154273782
6796.7534533146059963E-2525.969970699999980.20921914993211194
6786.8731775293858349E-2526.859985400000030.25035270392860615
6777.0551960190089788E-2527.90997310.29355943226792369
6767.1004686719136081E-2528.950012199999950.31751392793006633
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", - "image_path": "" - } - ] - } - ], - "index": 425, - "type": "chart_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 60 - spettro UV-Visibile e di emissione del copolimero ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "3c", - "style": [ - "bold", - "italic" - ] - }, - { - "type": "text", - "content": " in THF", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 426, - "type": "chart_caption" - } - ], - "index": 425 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I copolimeri " - }, - { - "type": "text", - "content": "3a", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", " - }, - { - "type": "text", - "content": "3b", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " e " - }, - { - "type": "text", - "content": "3c", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " in soluzione (THF) mostrano profili pressoché identici tra loro e fortemente simili a quello del monomero DPP di partenza (" - }, - { - "type": "text", - "content": "Figura 58", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", " - }, - { - "type": "text", - "content": "Figura 59", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", " - }, - { - "type": "text", - "content": "Figura 60", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "). Sia l'ampia banda di assorbimento, con λ" - }, - { - "type": "text", - "content": "max ", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "a circa 540-545 nm, relativa alla transizione π→π*, sia lo spettro di emissione, con λ" - }, - { - "type": "text", - "content": "max", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": " a circa 550 nm, ricalcano infatti il comportamento foto-fisico del core dichetopirrolopirrolico. Si nota come tutti i campioni presentino uno Stokes shift estremamente ridotto: questa forte sovrapposizione tra le bande di assorbimento ed emissione è indicativa di una notevole rigidità strutturale dello scheletro polimerico, il quale subisce una minima riorganizzazione conformazionale nel passaggio dallo stato fondamentale a quello eccitato." - } - ] - } - ], - "index": 427 - }, - { - "type": "table", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tabella 7 - dati spettroscopici dei copolimeri sintetizzati", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 428, - "type": "table_caption" - }, - { - "lines": [ - { - "spans": [ - { - "type": "table", - "html": "

copolimero

λmax, asb (nm)

λmax, ecc (nm)

Stokes shift (nm)

3a

540

547

7

3b

544

550

6

3c

542

552

10

" - } - ] - } - ], - "index": 429, - "type": "table_body" - } - ], - "index": 429 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tuttavia, sebbene in soluzione diluita i copolimeri mantengano queste eccellenti caratteristiche emissive, il loro comportamento allo stato solido risulta drasticamente differente. Come tipicamente si osserva nei sistemi " - }, - { - "type": "inline_equation", - "content": "\\pi" - }, - { - "type": "text", - "content": "-coniugati altamente planari, la deposizione allo stato solido favorisce una forte interazione intermolecolare. L'intenso impaccamento delle catene porta alla formazione di aggregati che disattivano i fluorofori attraverso percorsi di decadimento non radiativo. Questo effetto è visivamente confermato osservando i campioni polimerici depositati su vetrino: esposti all'illuminazione di una lampada UV (" - }, - { - "type": "text", - "content": "Figura 61", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), i film non mostrano alcuna emissione apprezzabile allo stato solido." - } - ] - } - ], - "index": 430 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/4ee04a7d6b36bbfeef99d8c40233deaab3e5e81eefb4e3d9c7dbce387219c598.jpg" - } - ] - } - ], - "index": 431, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 61 - film solidi dei copolimeri sotto lampada UV, in ordine copolimero ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "3a", - "style": [ - "bold", - "italic" - ] - }, - { - "type": "text", - "content": ", ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "3b", - "style": [ - "bold", - "italic" - ] - }, - { - "type": "text", - "content": ", ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "3c", - "style": [ - "bold", - "italic" - ] - } - ] - } - ], - "index": 432, - "type": "image_caption" - } - ], - "index": 431 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Proprio questa tendenza all'aggregazione, e al conseguente quenching emissivo nei film solidi, rappresenta la principale criticità per l'impiego di tali sistemi lineari in dispositivi optoelettronici. Per superare questo limite strutturale è necessario sfavorire l'avvicinamento incontrollato delle catene principali coniugate. È in quest'ottica che si è reso necessario il passaggio a un design macromolecolare più complesso, che giustifica la progettazione e la sintesi di un'architettura di tipo bottle-brush." - } - ] - } - ], - "index": 433 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Successivamente, i copolimeri sono stati caratterizzati mediante cromatografia a permeazione di gel (GPC) per determinare la distribuzione dei pesi molecolari" - } - ] - } - ], - "index": 434 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I risultati dell'analisi cromatografica riportati in " - }, - { - "type": "text", - "content": "Tabella 8", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " evidenziano masse molecolari medie numerali (" - }, - { - "type": "inline_equation", - "content": "\\overbar{M_{n}}" - }, - { - "type": "text", - "content": ") comprese tra circa 1400 e 2150 Da per i copolimeri sintetizzati. I campioni " - }, - { - "type": "text", - "content": "3a", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " e " - }, - { - "type": "text", - "content": "3c", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " presentano valori di " - }, - { - "type": "inline_equation", - "content": "\\overbar{M_{n}}" - }, - { - "type": "text", - "content": " del tutto equiparabili (rispettivamente 2149 e 2134 Da). Tuttavia, il copolimero " - }, - { - "type": "text", - "content": "3c", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " si distingue per una distribuzione delle catene polimeriche maggiormente omogenea, confermata dal valore di polidispersità più contenuto della serie (PD = 1.979)." - } - ] - } - ], - "index": 435 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'ottenimento di indici di polidispersità di questa entità è del tutto normale e atteso per questo sistema, trattandosi di una polimerizzazione non controllata. Nei processi convenzionali, infatti, l'assenza di un rigoroso controllo sulla cinetica di crescita e sulle reazioni di terminazione o trasferimento di catena porta a distribuzioni dei pesi molecolari ampie, con valori teorici e sperimentali di PD che si assestano tipicamente attorno a 2 (distribuzione più probabile di Flory) o superiori." - }, - { - "type": "text", - "content": "54", - "style": [ - "superscript" - ] - } - ] - } - ], - "index": 436 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il campione " - }, - { - "type": "text", - "content": "3b", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " mostra invece un andamento differente: pur registrando il valore più basso di " - }, - { - "type": "inline_equation", - "content": "\\overbar{M_{n}}" - }, - { - "type": "text", - "content": " (1402 Da), ad esso corrisponde la massa molecolare media ponderale (" - }, - { - "type": "inline_equation", - "content": "\\overbar{M_{w}}" - }, - { - "type": "text", - "content": ") più elevata (6439 Da). Questa discrepanza si traduce in un indice di polidispersità nettamente superiore (PD = 4.592), indicando una distribuzione dei pesi molecolari marcatamente ampia. Tale risultato suggerisce la presenza di una frazione significativa di specie oligomeriche a catena corta, che abbassano la media numerica, e di una porzione di macromolecole a peso molecolare più elevato che incrementano il valore ponderale." - } - ] - } - ], - "index": 437 - }, - { - "type": "table", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tabella 8 - Pesi molecolari e polidispersità determinati mediante GPC per i copolimeri 3a, 3b. 3c", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 438, - "type": "table_caption" - }, - { - "lines": [ - { - "spans": [ - { - "type": "table", - "html": "

Copolimero

Massa molecolare media numerica (Da)

Massa molecolare media ponderale (Da)

Polidispersità

(PD)

3a

2149

5526

2,571

3b

1402

6439

4,592

3c

2134

4223

1,979

" - } - ] - } - ], - "index": 439, - "type": "table_body" - } - ], - "index": 439 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Al fine di valutare le proprietà termiche dei materiali sintetizzati, i tre copolimeri sono stati analizzati mediante calorimetria a scansione differenziale (DSC). Dai termogrammi ottenuti è emerso che per tutti i campioni la temperatura di transizione vetrosa (Tg) si attesta intorno a -10 °C. A differenza di quanto si osserva per il 3HT, per i campioni in esame non si rilevano invece transizioni di fusione. Questo dato conferma l'ottenimento di un copolimero random: l'elevato disordine strutturale che lo caratterizza, infatti, impedisce al materiale di cristallizzare, nonostante i bassi pesi molecolari." - } - ] - } - ], - "index": 440 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "4.3. Polimeri bottle brush", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 441, - "anchor": "_Toc242438081", - "is_numbered_style": false, - "level": 2 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In questa fase del progetto di ricerca, l'attenzione si è focalizzata sulla sintesi e caratterizzazione di architetture polimeriche di tipo bottle brush. Lo scopo principale di questa progettazione strutturale è limitare i fenomeni di impaccamento intermolecolare tra le catene dei copolimeri precedentemente sintetizzati. Ridurre l'aggregazione tra le catene principali è un passaggio fondamentale per ottimizzare le prestazioni del materiale: l'ingombro sterico generato dalle catene laterali permette di isolare i backbone polimerici, portando ad un miglioramento delle proprietà spettroscopiche, limitando lo smorzamento della fluorescenza o quenching da aggregazione e, allo stesso tempo, favorendo una maggiore mobilità e flessibilità delle catene stesse." - } - ] - } - ], - "index": 442 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/af07237d5d3b9056fb6ba8c4a035fa954b1cb19f09ee7b255a2dc1576c9cd544.png" - } - ] - } - ], - "index": 443, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 62 - Effetto dell'intensità dello stacking π-π sull'emissione luminosa", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 444, - "type": "image_caption" - } - ], - "index": 443 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Dal punto di vista sintetico, la realizzazione di tale architettura mediante approccio “grafting from” richiede che la catena polimerica principale sia predisposta per comportarsi come macroiniziatore. Di conseguenza, al fine di innestare successivamente le catene laterali polimeriche, l'unità dichetopirrolopirrolica è stata progettata e sintetizzata introducendo una funzionalità ossidrilica terminale. Tale gruppo -OH costituisce il sito nucleofilo iniziatore per una reazione di polimerizzazione di tipo Ring Opening Polymerization (ROP), la quale permette di regolare il peso molecolare e mantenere una bassa dispersità delle catene laterali in accrescimento, parametri rilevanti per la sintesi di copolimeri bottle brush aventi un'architettura regolare e riproducibile." - } - ] - } - ], - "index": 445 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Stabilita la tecnica di polimerizzazione, per la costituzione delle catene laterali da accrescere la scelta è ricaduta sul policaprolattone (PCL). Tale decisione deriva da precedenti studi condotti all'interno del gruppo di ricerca. L'impiego del PCL offre infatti un duplice vantaggio, sia a livello sintetico che applicativo. La polimerizzazione del caprolattone via ROP, infatti, risulta essere un processo lineare ed efficiente. Per quanto riguarda le proprietà chimico-fisiche, invece, il PCL è caratterizzato da una bassa temperatura di transizione vetrosa (T" - }, - { - "type": "text", - "content": "g", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ") e da una buona solubilità nei comuni solventi organici" - }, - { - "type": "text", - "content": "55", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ". Queste caratteristiche garantiscono una notevole semplicità di lavorazione del prodotto e integrazione del sistema bottle brush all'interno di una matrice polimerica per l'ottenimento dei materiali finali." - } - ] - } - ], - "index": 446 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La reazione di polimerizzazione ROP presenta diversi possibili meccanismi" - }, - { - "type": "text", - "content": "56", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ", uno dei più sfruttati è quello di coordinazione-inserzione del monomero sul centro attivo dell’iniziatore. In particolare, la reazione di apertura dell’anello catalizzata da stagno ottanoato (Sn(Oct)" - }, - { - "type": "text", - "content": "2", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ") richiede generalmente l’aggiunta di co-iniziatori nucleofili come alcol" - }, - { - "type": "text", - "content": "56", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ". Si ha una prima reazione di scambio dei leganti, tra l’alcol e l’ottanoato del catalizzatore creando la specie attiva. A questo punto il centro metallico si coordina al carbonile del caprolattone, rendendo il carbonio più elettrofilo e favorendo l’attacco nucleofilo del gruppo alcolico con conseguente apertura dell’anello. La crescita del PCL prosegue quindi mediante attacchi successivi del terminale ossidrilico, che mantiene la reattività durante tutta la propagazione della catena (" - }, - { - "type": "text", - "content": "Figura 63", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 447 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/5e383d1d45b7de4b9fa9143e4e9ea41713e055a9d72ac00614059c40393f341c.jpg" - } - ] - } - ], - "index": 448, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 63 - meccanismo di reazione della ROP con gruppo alcolico come iniziatore", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 449, - "type": "image_caption" - } - ], - "index": 448 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La purificazione è stata condotta mediante precipitazione in non-solvente: la miscela di reazione è stata addizionata goccia a goccia all'interno di un largo eccesso di metanolo freddo. La scelta di questo specifico non-solvente è dettata dalle differenti solubilità delle specie in soluzione: mentre l'ε-caprolattone residuo e le altre specie a basso peso molecolare presentano un'elevata affinità per il metanolo, il copolimero ad alto peso molecolare vi risulta insolubile. Inoltre, l'impiego della bassa temperatura riduce ulteriormente la solubilità del polimero e ne favorisce la rapida coagulazione, massimizzando la resa del processo di precipitazione. Il polimero così precipitato è stato successivamente recuperato mediante filtrazione." - } - ] - } - ], - "index": 450 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Allo scopo di valutare in modo sistematico l'influenza della lunghezza delle catene laterali sulle proprietà finali del materiale, sono state preparate due serie di polimeri bottle brush. Queste serie sono state ottenute impiegando rispettivamente i copolimeri " - }, - { - "type": "text", - "content": "3b", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " e " - }, - { - "type": "text", - "content": "3c", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " in qualità di macroiniziatori. Sebbene fosse stato sintetizzato anche un terzo copolimero " - }, - { - "type": "text", - "content": "3a", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", il suo impiego per le successive fasi di grafting è stato scartato a causa della scarsa efficienza della sua via sintetica. Nello specifico, le basse rese di reazione e le difficoltà incontrate nel work-up per l'isolamento del prodotto puro portavano a notevoli perdite di materiale. Inoltre, dal punto di vista dell’efficienza di processo, l'isolamento di quantità utili di questo copolimero avrebbe richiesto volumi di solventi e costi di reagenti molto elevati. Di conseguenza, per garantire la fattibilità tecnica ed economica della ricerca, si è scelto di utilizzare esclusivamente i macroiniziatori " - }, - { - "type": "text", - "content": "3b", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " e " - }, - { - "type": "text", - "content": "3c", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 451 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Sfruttando l'elevato grado di controllo della reazione di ROP, è stato possibile modulare la lunghezza delle catene in accrescimento variando il rapporto molare tra il monomero (ε-caprolattone) e i siti iniziatori (-OH) presenti sul backbone. Seguendo questo approccio, per ciascuno dei due precursori copolimerici sono stati sintetizzati tre differenti polimeri dotate di catene laterali in PCL con pesi molecolari di circa 1500 Da, 5000 Da e 10000 Da (" - }, - { - "type": "text", - "content": "Tabella 9", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 452 - }, - { - "type": "table", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tabella 9 - lunghezza delle catene in PCL nei polimeri bottle brush", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 453, - "type": "table_caption" - }, - { - "lines": [ - { - "spans": [ - { - "type": "table", - "html": "

Copolimero

Polimero bottle brush

Lunghezza catene di PCL (Da)

3b

3.1b

1500

3.2b

5000

3.3b

10000

3c

3.1c

1500

3.2c

5000

3.3c

10000

" - } - ] - } - ], - "index": 454, - "type": "table_body" - } - ], - "index": 454 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Al fine di determinare la quantità esatta di monomero necessaria per raggiungere ciascuno di questi pesi molecolari target, è stata impiegata la seguente equazione:" - } - ] - } - ], - "index": 455 - }, - { - "type": "interline_equation", - "lines": [ - { - "spans": [ - { - "type": "interline_equation", - "content": "V_{CL}=\\frac{\\frac{m_{backbone}}{MW_{backbone}}\\times DP_{backbone}\\times \\chi _{DPP}\\times 2\\times Mn_{teorico}}{\\rho _{CL}}" - } - ] - } - ], - "index": 456 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il termine " - }, - { - "type": "inline_equation", - "content": "V_{CL}" - }, - { - "type": "text", - "content": " rappresenta il volume di caprolattone da prelevare e inserire in reazione espresso in mL. Questo parametro è calcolato a partire dalla massa del copolimero lineare di partenza pesata (" - }, - { - "type": "inline_equation", - "content": "m_{backbone}" - }, - { - "type": "text", - "content": ", in g) e dal suo peso molecolare ricavato via GPC (" - }, - { - "type": "inline_equation", - "content": "MW_{backbone}" - }, - { - "type": "text", - "content": ", in g/mol), il cui rapporto restituisce le moli di backbone utilizzate. Tale valore viene moltiplicato per il grado di polimerizzazione del copolimero lineare di partenza (" - }, - { - "type": "inline_equation", - "content": "DP_{backbone}" - }, - { - "type": "text", - "content": "), per la frazione molare delle unità di DPP al suo interno (" - }, - { - "type": "inline_equation", - "content": "\\chi _{DPP}" - }, - { - "type": "text", - "content": ") e per il valore " - }, - { - "type": "inline_equation", - "content": "2" - }, - { - "type": "text", - "content": ", corrispondente al numero di gruppi idrossilici presenti per ogni unità di DPP. Il prodotto ottenuto viene a sua volta moltiplicato per il peso molecolare teorico desiderato per la singola catena laterale di PCL (" - }, - { - "type": "inline_equation", - "content": "Mn_{teorico}" - }, - { - "type": "text", - "content": ", espresso in Da). Infine, l'intero numeratore è diviso per la densità dell'" - }, - { - "type": "inline_equation", - "content": "\\varepsilon" - }, - { - "type": "text", - "content": "-caprolattone liquido alla temperatura di prelievo (" - }, - { - "type": "inline_equation", - "content": "\\rho _{CL}" - }, - { - "type": "text", - "content": ", in g/mL) per convertire la massa totale del monomero nel volume da prelevare." - } - ] - } - ], - "index": 457 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Per confermare l'avvenuta formazione delle catene laterali, tutti i polimeri sintetizzati sono stati analizzati mediante spettroscopia ¹H-NMR. L'effettiva polimerizzazione dell'ε-caprolattone è stata verificata osservando la comparsa dei segnali caratteristici del PCL, in particolare il caratteristico tripletto a circa 4.0 ppm, attribuibile ai protoni metilenici adiacenti all'ossigeno del legame estereo (-CH" - }, - { - "type": "text", - "content": "2", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "-O-), e il segnale a 2.3 ppm relativo ai protoni in alfa al carbonile. Poiché gli spettri risultano del tutto analoghi per l'intera serie di campioni, differendo esclusivamente per i valori di integrazione dei segnali in funzione del peso molecolare, in " - }, - { - "type": "text", - "content": "Figura 64 ", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "riporta lo spettro del polimero " - }, - { - "type": "text", - "content": "3.1b", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", rappresentativo per tutti i composti sintetizzati." - } - ] - } - ], - "index": 458 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/e5c7709e972d150950dac9ce997e72834c0dc9a43529a4cfdacf675b2fbf7dd2.png" - } - ] - } - ], - "index": 459, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 64 - spettro ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "1", - "style": [ - "italic", - "superscript" - ] - }, - { - "type": "text", - "content": "H-NMR del polimero 3.1b in CDCl", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "3", - "style": [ - "italic", - "subscript" - ] - } - ] - } - ], - "index": 460, - "type": "image_caption" - } - ], - "index": 459 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Entrambe le serie di polimeri bottle brush sintetizzati sono state sottoposte a spettroscopia FT-IR. Al fine di evidenziare l'accrescimento delle catene laterali, sono stati riportati gli spettri infrarossi sovrapposti delle due serie polimeriche (" - }, - { - "type": "text", - "content": "Figura 65, Figura 66", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "). Ponendo alla base la traccia del relativo copolimero macroiniziatore, è possibile apprezzare in modo diretto le variazioni spettrali indotte dalle catene laterali di policaprolattone." - } - ] - } - ], - "index": 461 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'analisi comparativa conferma chiaramente il successo della reazione. Per entrambe le serie, nello spettro del precursore (traccia rossa) è visibile un assorbimento largo nella regione tra 3600 e 3200 cm⁻¹, tipico dello stretching del gruppo ossidrilico (-OH) terminale. A seguito della polimerizzazione, tale banda risulta del tutto assente nei profili dei polimeri bottle brush, a conferma del coinvolgimento dell'ossidrile come sito iniziatore per la polimerizzazione. Parallelamente, gli spettri dei copolimeri innestati risultano dominati dai segnali caratteristici del PCL. Spicca in particolar modo la comparsa di un picco molto stretto e ad alta intensità centrato a circa 1720 cm⁻¹, attribuibile allo stretching del gruppo carbonilico (C=O) estereo delle unità di caprolattone. Rispetto al copolimero di riferimento, si osserva inoltre una maggiore definizione delle bande relative allo stretching simmetrico e asimmetrico dei legami C-H alifatici (nella regione 2950-2860 cm⁻¹), insieme ai forti segnali di stretching del legame C-O-C nella regione della fingerprint (1240-1160 cm⁻¹)." - } - ] - } - ], - "index": 462 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Come atteso, all'aumentare del peso molecolare delle catene laterali, il profilo vibrazionale del materiale tende a coincidere quasi interamente con quello del PCL omopolimero. Questo fenomeno è dovuto al fatto che la massa delle lunghe catene di policaprolattone va a coprire progressivamente i segnali meno intensi provenienti dal backbone del fluoroforo." - } - ] - } - ], - "index": 463 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/aee89434079292419db42d834206a12f90edf335898d67af13028f6f3d04c928.png" - } - ] - } - ], - "index": 464, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 65 - spettri FT-IR dei polimeri bottle brush ottenuti a partire dal copolimero 3b (verde):", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 465, - "type": "image_caption" - } - ], - "index": 464 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "polimero 3.1b (arancione), polimero 3.2b (rosa), polimero 3.3b (azzurro)", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 466 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/cbe62cb1e190227f5fd74fe12b543905276918aa81971d52027734db5712c35a.png" - } - ] - } - ], - "index": 467, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 66 - spettri FT-IR dei polimeri bottle brush ottenuti a partire dal copolimero 3c (verde): ", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 468, - "type": "image_caption" - } - ], - "index": 467 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "polimero 3.1c (arancione), polimero 3.2c (rosa), polimero 3.3c (azzurro)", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 469 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La caratterizzazione foto-fisica dei polimeri è stata effettuata mediante spettroscopia di assorbimento (UV-Vis) ed emissione (" - }, - { - "type": "text", - "content": "Figura 67", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 470 - }, - { - "type": "chart", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "chart", - "content": "
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6929.9715444811758924E-2508.04998783.7648081972433776E-3
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", - "image_path": "" - } - ] - } - ], - "index": 476, - "type": "chart_body" - } - ], - "index": 476 - }, - { - "type": "table", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "table", - "html": "
" - } - ] - } - ], - "index": 477, - "type": "table_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 67 - spettri UV-Visibile (linea continua) e di emissione (linea tratteggiata) dei polimeri bottle brush in THF", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 478, - "type": "table_caption" - } - ], - "index": 477 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I massimi di assorbimento per l'intera libreria di polimeri (" - }, - { - "type": "text", - "content": "Tabella 10", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") rientrano in un range molto ristretto, compreso tra 544 e 554 nm, mentre i massimi di emissione ricadono nell'intervallo tra 557 e 564 nm. Le lievi fluttuazioni registrate all'interno delle due serie polimeriche (derivate rispettivamente dai copolimeri " - }, - { - "type": "text", - "content": "3b", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " e " - }, - { - "type": "text", - "content": "3c", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") non seguono un andamento lineare in funzione del peso molecolare del PCL e risultano trascurabili. Tale costanza nei valori di λ" - }, - { - "type": "text", - "content": "max ", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "rappresenta una conferma del fatto che l'incremento dell'ingombro sterico non perturba i livelli energetici e la natura delle transizioni elettroniche del core dichetopirrolopirrolico." - } - ] - } - ], - "index": 479 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Un ulteriore dato quantitativo di particolare rilevanza è rappresentato dai valori dello Stokes shift, i quali si mantengono estremamente ridotti, oscillando in un ristretto intervallo compreso tra gli 8 e i 14 nm. Questo parametro rappresenta una conferma della validità del design molecolare adottato: da un lato, i domini flessibili di policaprolattone generano l’ingombro sterico necessario per allontanare le catene principali tra di loro, limitando l'impaccamento e garantendo una maggiore mobilità al sistema; dall'altro lato, il grafting non introduce distorsioni alla geometria del backbone. Il mantenimento di un basso Stokes shift verifica che il core fluorescente conserva la sua conformazione planare e non subisce rilassamenti indesiderati nel passaggio allo stato eccitato, preservando così intatte le sue proprietà emissive." - } - ] - } - ], - "index": 480 - }, - { - "type": "table", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tabella 10 - dati spettroscopici dei polimeri sintetizzati", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 481, - "type": "table_caption" - }, - { - "lines": [ - { - "spans": [ - { - "type": "table", - "html": "

Polimero

λmax, abs (nm)

λmax, ex(nm)

Stokes shift (nm)

3.1b

554

562

8

3.2b

550

564

14

3.3b

553

563

10

3.1c

547

561

14

3.2c

544

557

13

3.3c

553

564

11

" - } - ] - } - ], - "index": 482, - "type": "table_body" - } - ], - "index": 482 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "A completamento della caratterizzazione strutturale, l'effettivo accrescimento delle catene laterali e le dimensioni macromolecolari dei sistemi bottle brush sono stati valutati mediante Cromatografia a Permeazione di Gel (GPC). Questa indagine risulta fondamentale non solo per determinare i pesi molecolari medi (" - }, - { - "type": "inline_equation", - "content": "\\overbar{M_{n}}" - }, - { - "type": "text", - "content": " e " - }, - { - "type": "inline_equation", - "content": "\\overbar{M_{w}}" - }, - { - "type": "text", - "content": ") e gli indici di dispersità (PD) dei materiali sintetizzati, ma anche per verificare a posteriori il grado di controllo esercitato dalla polimerizzazione per apertura di anello (ROP). Il confronto tra i valori sperimentali ricavati dai cromatogrammi e i pesi molecolari target previsti in fase di progettazione sintetica (rispettivamente 1500, 5000 e 10000 Da) permette infatti di confermare l'efficacia dell'approccio grafting-from e la corretta architettura finale dei copolimeri." - } - ] - } - ], - "index": 483 - }, - { - "type": "table", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tabella 11 - Pesi molecolari e polidispersità dei polimeri bottle brush determinati mediante GPC ", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 484, - "type": "table_caption" - }, - { - "lines": [ - { - "spans": [ - { - "type": "table", - "html": "

Polimero

Massa molecolare media numerale (Da)

Massa molecolare media ponderale (Da)

Polidispersità

(PD)

3.1b

12188

18536

1,521

3.2b

17302

22737

1,314

3.3b

21269

26328

1,238

3.1c

13999

18219

1,301

3.2c

19119

24376

1,275

3.3c

14445

19521

1,351

" - } - ] - } - ], - "index": 485, - "type": "table_body" - } - ], - "index": 485 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I valori di peso molecolare ottenuti tramite GPC (" - }, - { - "type": "text", - "content": "Tabella 11", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") risultano significativamente sottostimati rispetto ai valori teorici a causa del principio di funzionamento della tecnica unito alla particolare architettura bottle brush dei polimeri. La GPC, infatti, separa le macromolecole in base al loro volume idrodinamico, restituendo valori relativi agli standard di calibrazione utilizzati, in questo caso un polimero lineare corrispondente a polistirene. A parità di peso molecolare reale, un polimero altamente ramificato assume una conformazione in soluzione molto più compatta rispetto a un polimero lineare, possedendo quindi un volume idrodinamico nettamente inferiore. Questo fa sì che il polimero ramificato penetri maggiormente nei pori della colonna, eluendo agli stessi tempi di polimeri lineari molto più corti. Tale sottostima è proporzionale all'ingombro delle catene laterali: con innesti in PCL a basso peso molecolare (circa 1500 Da), l'approssimazione a un comportamento lineare risulta più attendibile, restituendo valori GPC attorno ai 12000 Da." - } - ] - } - ], - "index": 486 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Al contrario, aumentando il peso molecolare dei segmenti laterali (ad esempio stimando tre catene per lato, per un peso teorico atteso di circa 62000 Da), la drastica compattazione strutturale porta a una sottostima del peso reale che si aggira intorno al 70%." - }, - { - "type": "text", - "content": "57", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": " In questi sistemi, dunque, i dati ottenuti non indicano il peso molecolare assoluto o una bassa resa, ma confermano indirettamente la presenza di una struttura ramificata altamente impaccata e, sebbene non corrispondenti ai valori reali, permettono un confronto diretto tra i diversi polimeri sintetizzati." - } - ] - } - ], - "index": 487 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tuttavia, il polimero 3.3c presenta un valore di peso molecolare che si discosta dall'andamento generale degli altri campioni; ciò potrebbe essere dovuto al fatto che, essendo il materiale di partenza di natura random, la presenza di possibili elevate concentrazioni locali di dichetopirrolopirroli e relativi ossidrili nel copolimero, abbia causato una ridotta crescita dei polimeri laterali per via dell’ingombro sterico delle catene in crescita. Tali discrepanze nei valori di peso molecolare saranno comunque maggiormente investigate in futuro attraverso ulteriori analisi." - } - ] - } - ], - "index": 488 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Al fine di superare le limitazioni associate all'analisi GPC, si è ricorsi all'utilizzo della spettroscopia H-NMR. Il calcolo si fonda sulla valutazione del grado di polimerizzazione delle singole catene laterali di PCL." - } - ] - } - ], - "index": 489 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'equazione generale utilizzata per ricavare il peso molecolare totale (" - }, - { - "type": "inline_equation", - "content": "MW_{tot}" - }, - { - "type": "text", - "content": ") del copolimero ramificato è la seguente:" - } - ] - } - ], - "index": 490 - }, - { - "type": "interline_equation", - "lines": [ - { - "spans": [ - { - "type": "interline_equation", - "content": "MW_{tot}=MW_{backbone}+\\left[\\left(\\frac{I_{4.05}}{I_{3.65}}\\times MW_{CL}\\right)\\times \\left(DP_{backbone}\\times \\chi _{DPP}\\times 2\\right)\\right]" - } - ] - } - ], - "index": 491 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Equazione 10 - calcolo del peso molecolare dei polimeri bottle brush mediante 1H-NMR", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 492 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Nello specifico, il numero di unità ripetenti per catena laterale è stato ricavato dal rapporto tra l'area del segnale relativo ai protoni metilenici interni alla catena (" - }, - { - "type": "inline_equation", - "content": "I_{4.05}" - }, - { - "type": "text", - "content": " per il gruppo –CH2O–CO–, a circa 4.05 ppm) e l'integrale dei protoni metilenici terminali adiacenti al gruppo ossidrilico (" - }, - { - "type": "inline_equation", - "content": "I_{3.65}" - }, - { - "type": "text", - "content": " per il gruppo –CH2-OH, a circa 3.65 ppm), il cui valore è stato posto convenzionalmente pari a 1." - } - ] - } - ], - "index": 493 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il peso molecolare della singola catena di PCL così ottenuto, pari al termine " - }, - { - "type": "inline_equation", - "content": "\\left(\\frac{I_{4.05}}{I_{3.65}}\\times MW_{CL}\\right)" - }, - { - "type": "text", - "content": " dove " - }, - { - "type": "inline_equation", - "content": "MW_{CL}" - }, - { - "type": "text", - "content": " è il peso molecolare dell'unità ripetente del caprolattone, è stato successivamente moltiplicato per il numero medio di siti di polimerizzazione presenti per macromolecola. Quest'ultimo parametro è stato stimato a partire dal grado di polimerizzazione del copolimero lineare di partenza (" - }, - { - "type": "inline_equation", - "content": "DP_{backbone}" - }, - { - "type": "text", - "content": "), ricavato dai valori GPC, e dal rapporto molare tra le unità di 3HT e DPP ottenuto via NMR (che definisce la frazione molare " - }, - { - "type": "inline_equation", - "content": "\\chi _{DPP}" - }, - { - "type": "text", - "content": "), considerando che ogni unità di DPP reca due gruppi idrossilici di innesco. Infine, il peso molecolare totale dei copolimeri ramificati è stato calcolato sommando la massa complessiva delle catene laterali di PCL al peso molecolare del backbone lineare (" - }, - { - "type": "inline_equation", - "content": "MW_{backbone}" - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 494 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I valori calcolati con questo metodo offrono una stima molto più vicina ai valori teorici e sono riassunti in " - }, - { - "type": "text", - "content": "Tabella 12.", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 495 - }, - { - "type": "table", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tabella 12 - pesi molecolari dei polimeri bottle brush determinati via ", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "1", - "style": [ - "italic", - "superscript" - ] - }, - { - "type": "text", - "content": "H-NMR", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 496, - "type": "table_caption" - }, - { - "lines": [ - { - "spans": [ - { - "type": "table", - "html": "

Polimero

Peso Molecolare teorico (Da)

Peso Molecolare da 1H-NMR (Da)

3.1b

6500

8900

3.2b

18000

20500

3.3b

34500

88000

3.1c

10000

18200

3.2c

28500

35500

3.3c

55000

41300

" - } - ] - } - ], - "index": 497, - "type": "table_body" - } - ], - "index": 497 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Anche per i polimeri bottle brush è stata effettuata l’analisi termica mediante DSC. Dai termogrammi registrati è emerso che le principali transizioni termiche si mantengono pressoché costanti per tutti i polimeri sintetizzati, in quanto dominate dal comportamento del policaprolattone (PCL). Nello specifico, la temperatura di fusione (Tm) risulta compresa nel range tra 55 °C e 60 °C, mentre la temperatura di cristallizzazione (Tc) si attesta nell'intervallo tra 25 °C e 35 °C." - } - ] - } - ], - "index": 498 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Questo comportamento è strettamente legato alla struttura tridimensionale di queste macromolecole: le transizioni termiche osservate sono infatti fondamentalmente governate dai segmenti a base di caprolattone che costituiscono le catene laterali. Data l'elevata densità di grafting e rappresentando il caprolattone la frazione preponderante del sistema, la mobilità di queste catene e la loro propensione a cristallizzare dettano le proprietà termiche dell'intero materiale. Di conseguenza, l'influenza dello scheletro polimerico principale viene minimizzata, rendendo i profili termici essenzialmente indipendenti dalle lievi variazioni strutturali tra i diversi polimeri." - } - ] - } - ], - "index": 499 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/0173034d196ba93044667ab8a1fa2d4b9d69f60d679bad29840de373b8319dea.jpg" - } - ] - } - ], - "index": 500, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 68 - esempio di termogramma dei polimeri bottle brush realizzati (in figura l'analisi del campione 3.1c)", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 501, - "type": "image_caption" - } - ], - "index": 500 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "4.4. Ciclovoltammetrie", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 502, - "anchor": "_Toc242438082", - "is_numbered_style": false, - "level": 2 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La ciclovoltammetria (CV) è una tecnica elettrochimica dinamica, appartenente alla famiglia delle tecniche voltammetriche, ampiamente impiegata per studiare i processi di ossido-riduzione (redox)." - } - ] - } - ], - "index": 503 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In ambito macromolecolare e dei materiali coniugati, questa tecnica risulta utile per investigare le proprietà di trasferimento elettronico, la stabilità elettrochimica e, in particolare, per determinare il gap energetico elettrochimico dei materiali." - } - ] - } - ], - "index": 504 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "4.4.1. Ciclovoltammetrie su polimeri elettroattivi", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 505, - "anchor": "_Toc242438083", - "is_numbered_style": false, - "level": 3 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Alla luce dei principi teorici esposti nel " - }, - { - "type": "text", - "content": "paragrafo 3.3", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", l'impiego della ciclovoltammetria si è rivelato uno step analitico fondamentale per la caratterizzazione dei polimeri sintetizzati in questo progetto di tesi. L'obiettivo primario di tale indagine è stato quello di studiare il comportamento elettrochimico derivante dall'estesa coniugazione π presente lungo la catena macromolecolare. Infatti, il grado di delocalizzazione elettronica all'interno di questo sistema coniugato suggerisce un potenziale comportamento da semiconduttore; la tecnica della ciclovoltammetria ha permesso di supportare questa ipotesi verificando la loro elettroattività e stimando un band gap elettrochimico compatibile con i materiali semiconduttori." - } - ] - } - ], - "index": 506 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Nello specifico, l'analisi è stata condotta per identificare ed analizzare i processi redox a carico dello scheletro polimerico, individuando i potenziali di onsetnecessari per la stima del gap energetico." - } - ] - } - ], - "index": 507 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La tecnica è stata impiegata per indagare la cinetica dei processi redox e il loro grado di reversibilità, un parametro fondamentale per comprendere i limiti strutturali del materiale. In quest'ottica, l'osservazione del profilo voltammetrico e l'andamento delle correnti in scansioni multiple consecutive costituiscono uno strumento di caratterizzazione essenziale: queste due analisi consentono di discriminare tra un sistema in grado di tollerare ciclicamente il trasferimento di carica e l'eventuale presenza di reazioni secondarie di degradazione elettrochimica." - } - ] - } - ], - "index": 508 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Lo studio voltammetrico funge quindi da ponte tra la validazione dell'architettura elettronica dei polimeri bottle brush sintetizzati e l'indagine della loro effettiva stabilità operazionale." - } - ] - } - ], - "index": 509 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "4.4.2. Metodologie di analisi voltammetrica ", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 510, - "anchor": "_Toc242438084", - "is_numbered_style": false, - "level": 3 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'analisi dei voltammogrammi è stata strutturata in due parti: una qualitativa, legata all'osservazione della forma del tracciato, e una quantitativa, basata sull'estrazione di valori numerici specifici." - } - ] - } - ], - "index": 511 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In primo luogo, si è studiato l'andamento delle curve per capire come il polimero risponde allo scambio di elettroni. I materiali coniugati, infatti, possono subire due processi principali: l'estrazione di elettroni dalla loro struttura, che corrisponde a un'ossidazione ed è nota in letteratura come p-doping, e l'iniezione di elettroni, che corrisponde a una riduzione ed è definita n-doping. Osservando la forma dei picchi di ossidazione e riduzione nel grafico, e verificando se sono presenti i rispettivi picchi di ritorno, è possibile capire se il processo è reversibile o meno, valutando così la stabilità del materiale quando viene sottoposto a stress elettrochimico." - } - ] - } - ], - "index": 512 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In secondo luogo, l'analisi si è concentrata sulla determinazione esatta del potenziale al quale questi due processi hanno inizio, chiamati potenziali di onset. Ricavare questi valori dal grafico è il passaggio fondamentale dell'intera analisi, poiché rappresentano i dati di partenza necessari per calcolare il gap energetico del polimero sintetizzato." - } - ] - } - ], - "index": 513 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Per illustrare nel dettaglio la procedura pratica di elaborazione dei dati che è stata applicata a tutti i materiali, si riporta a titolo esemplificativo il voltammogramma ciclico relativo al polimero 3.2.c (" - }, - { - "type": "text", - "content": "Figura 69", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "). L'approccio di analisi descritto per questo specifico tracciato è stato ripetuto sistematicamente su tutti i voltammogrammi acquisiti per ricavare i parametri elettrochimici di ciascun polimero sintetizzato." - } - ] - } - ], - "index": 514 - }, - { - "type": "chart", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "chart", - "content": "
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", - "image_path": "" - } - ] - } - ], - "index": 515, - "type": "chart_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 69 - Voltammogramma ciclico del polimero 3.2.c registrato a una velocità di scansione di 0.05 V/s in soluzione di THF con TBAPF", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "6", - "style": [ - "italic", - "subscript" - ] - }, - { - "type": "text", - "content": " 0.1 M.", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 516, - "type": "chart_caption" - } - ], - "index": 515 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'analisi qualitativa delle curve corrente/potenziale rivela la natura dei processi di ossido-riduzione dello scheletro coniugato, evidenziandone il grado di reversibilità." - } - ] - } - ], - "index": 517 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In un sistema elettrochimicamente reversibile, il processo di trasferimento elettronico si manifesta con la comparsa di un picco diretto e di un corrispondente picco di ritorno durante la scansione inversa, caratterizzati da un rapporto tra l'intensità della corrente anodica e catodica (I" - }, - { - "type": "text", - "content": "pa", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": "/I" - }, - { - "type": "text", - "content": "pc", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ") prossimo all'unità. Nei tracciati registrati per la serie di polimeri in esame, al contrario, si osserva sistematicamente un marcato discostamento da questo comportamento ideale. Dal punto di vista grafico, l'irreversibilità si palesa attraverso lo sviluppo di ampie onde faradiche durante le scansioni di andata, alle quali non fa seguito alcun corrispondente picco di ritorno termodinamicamente simmetrico." - } - ] - } - ], - "index": 518 - }, - { - "type": "chart", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "chart", - "content": "
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", - "image_path": "" - } - ] - } - ], - "index": 519, - "type": "chart_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 70 - Voltammogramma ciclico del polimero 3.2.c registrato a diverse velocità di scansione", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 520, - "type": "chart_caption" - } - ], - "index": 519 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Questo comportamento è chiaramente evidenziato dai voltammogrammi riportati in " - }, - { - "type": "text", - "content": "Figura 70", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ". Analizzando i tracciati ottenuti a velocità di scansione crescenti, non solo si osserva la totale assenza di onde di scarica simmetriche durante la scansione di ritorno, ma si rileva anche una progressiva diminuzione dell'intensità delle onde faradiche. Questa perdita di segnale indica che la specie generata durante l’analisi non è limitata a una semplice irreversibilità del trasferimento di carica, ma risulta intrinsecamente instabile. Il calo della corrente registrata testimonia infatti una degradazione e una conseguente perdita di materiale elettroattivo utile all'interfaccia elettrodo-soluzione." - } - ] - } - ], - "index": 521 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Dal punto di vista chimico e fisico, questo profilo voltammetrico indica che il trasferimento elettronico all'interfaccia elettrodo-soluzione è strettamente accoppiato a fenomeni secondari che consumano o alterano irreversibilmente la specie generata elettronicamente. Quando il polimero neutro viene sottoposto a scansione anodica, ovvero ad un drogaggio elettrochimico di tipo p, la rimozione di elettroni dal sistema π-coniugato comporta la formazione di specie con carica positiva, definibili come polaroni, radicali cationi. Analogamente, ai potenziali catodici, attraverso un drogaggio di tipo n, l'iniezione di elettroni genera le rispettive specie radical-anioniche." - } - ] - } - ], - "index": 522 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La mancanza delle onde voltammetriche di ritorno conferma che queste macromolecole cariche risultano altamente instabili nelle condizioni sperimentali adottate. In un sistema ideale governato da un meccanismo di tipo E, puramente elettrochimico, la reazione si limiterebbe al solo trasferimento di elettroni: la specie ossidata o ridotta rimarrebbe stabile all'interfaccia elettrodo-soluzione e subirebbe il processo elettrochimico inverso in modo simmetrico una volta invertita la direzione della scansione del potenziale. Nei materiali in esame si instaura invece un meccanismo di tipo EC, elettrochimico-chimico, nel quale il trasferimento di carica iniziale (fase E) genera un intermedio altamente reattivo che viene immediatamente consumato da una reazione chimica secondaria (fase C) prima di poter restituire o accettare nuovamente l'elettrone scambiato. Tale instabilità si traduce tipicamente in reazioni chimiche irreversibili di degradazione del materiale, che possono includere reazioni di accoppiamento tra le catene polimeriche radicaliche, sovraossidazione o l'insorgenza di reazioni parassite. Di conseguenza, a causa del consumo chimico della specie elettroattiva transitoria, il materiale non è in grado di ripristinare il proprio stato neutro iniziale, come evidenziato dall'assoluta asimmetria dei cicli voltammetrici registrati." - } - ] - } - ], - "index": 523 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Oltre all'indagine qualitativa, i voltammogrammi sono stati sottoposti a un'elaborazione quantitativa finalizzata all'estrapolazione dei potenziali di " - }, - { - "type": "text", - "content": "onset", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": " (Eonset). Infatti, a causa della marcata irreversibilità e dell'ampiezza delle onde faradiche descritte in precedenza, i potenziali di picco (" - }, - { - "type": "inline_equation", - "content": "E_{p}" - }, - { - "type": "text", - "content": ") sono fortemente alterati dalla rapida degradazione delle specie cariche appena formate. Per questo motivo, non rappresentano un parametro affidabile per calcolare i veri livelli energetici del materiale. L'utilizzo del potenziale di " - }, - { - "type": "text", - "content": "onset", - "style": [ - "subscript" - ] - }, - { - "type": "text", - "content": ", al contrario, consente di approssimare con maggiore accuratezza la minima energia necessaria per innescare i primissimi trasferimenti elettronici all'interfaccia, correlandosi direttamente ai limiti di banda del materiale." - } - ] - } - ], - "index": 524 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La determinazione di questi valori è stata condotta applicando il metodo grafico dell'intersezione delle tangenti (" - }, - { - "type": "text", - "content": "Figura 69", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "). La costruzione geometrica richiede innanzitutto di tracciare la linea di base che precede il picco (baseline). Questa retta modella la risposta del sistema in termini di pura corrente capacitiva, legata alla carica del doppio strato elettrico; essa viene registrata in un intervallo di potenziale in cui il polimero risulta ancora elettrochimicamente inerte, immediatamente prima dell'avvio delle reazioni redox. Successivamente, si procede delineando una seconda retta, tangente al punto di massima pendenza del fronte di salita dell'onda voltammetrica. Questa linea descrive il rapido incremento di corrente associato al vero e proprio processo faradico di drogaggio, ovvero il momento in cui l'iniezione o l'estrazione di elettroni diventa il processo predominante. Il potenziale di onset viene definito graficamente dal punto esatto di intersezione tra l'estrapolazione della corrente capacitiva precedente al picco e la tangente al processo faradico. Proiettando tale intersezione sull'asse delle ascisse, è possibile ricavare il valore in Volt: applicando la procedura all'onda anodica si ottiene il potenziale di onset di ossidazione (" - }, - { - "type": "inline_equation", - "content": "E_{onset}^{ox}" - }, - { - "type": "text", - "content": "), mentre applicandola all'onda catodica si ricava il potenziale di onset di riduzione (" - }, - { - "type": "inline_equation", - "content": "E_{onset}^{red}" - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 525 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Applicando sistematicamente questo metodo a tutti i tracciati sperimentali, è stato possibile escludere l'interferenza della corrente di fondo, individuando l'esatto potenziale redox di ciascun copolimero in modo chiaro e riproducibile." - } - ] - } - ], - "index": 526 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I valori di potenziale estratti graficamente sono quantità relative, strettamente dipendenti dalle caratteristiche specifiche dell'elettrodo di riferimento ad Ag/AgCl impiegato e dalle fluttuazioni termodinamiche del sistema solvente/elettrolita. Per convertire queste misure in parametri energetici assoluti, confrontabili con la letteratura, si rende indispensabile una calibrazione dell'asse dei potenziali. A tale scopo è stato impiegato il ferrocene come standard redox interno." - } - ] - } - ], - "index": 527 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Quest’ultimo costituisce il classico riferimento per le misurazioni elettrochimiche in solventi organici poiché presenta una coppia redox (Fc/Fc" - }, - { - "type": "text", - "content": "+", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": ") altamente reversibile, chimicamente stabile e il cui potenziale è ben noto. Dal punto di vista termodinamico, l'energia associata al processo di ossidazione del ferrocene è convenzionalmente posta a - 4.8 eV rispetto al livello energetico del vuoto. Registrando il voltammogramma del ferrocene al termine di ogni analisi e ricavandone il potenziale di semionda sperimentale, è stato possibile calibrare i dati prima della loro elaborazione grafica. L'asse delle ascisse dei voltammogrammi è stato normalizzato sottraendo il potenziale di semionda del ferrocene a tutti i valori di potenziale registrati, riferendo così i tracciati direttamente alla scala del Fc/Fc" - }, - { - "type": "text", - "content": "+", - "style": [ - "superscript" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 528 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I potenziali di onset ricavati graficamente da questi voltammogrammi normalizzati sono stati quindi impiegati per calcolare i livelli energetici degli orbitali di frontiera HOMO e LUMO dei copolimeri, applicando le seguenti equazioni empiriche:" - } - ] - } - ], - "index": 529 - }, - { - "type": "interline_equation", - "lines": [ - { - "spans": [ - { - "type": "interline_equation", - "content": "E_{HOMO}=-\\left(E_{onset}^{ox}+4.8\\right) eV E_{LUMO}=-\\left(E_{onset}^{red}+4.8\\right) eV" - } - ] - } - ], - "index": 530 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Equazione 11 - calcolo dei livelli energetici HOMO e LUMO", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 531 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Infine, la differenza tra il livello LUMO e il livello HOMO ha permesso di ricavare il bandgap elettrochimico (" - }, - { - "type": "inline_equation", - "content": "E_{g}" - }, - { - "type": "text", - "content": ") per ciascun materiale sintetizzato:" - } - ] - } - ], - "index": 532 - }, - { - "type": "interline_equation", - "lines": [ - { - "spans": [ - { - "type": "interline_equation", - "content": "E_{g}=E_{LUMO}-E_{HOMO}" - } - ] - } - ], - "index": 533 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Equazione 12 - bandgap elettrochimico", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 534 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'applicazione sistematica di queste equazioni ha permesso di tradurre i dati voltammetrici normalizzati in un quadro quantitativo e completo delle proprietà optoelettroniche dei materiali." - } - ] - } - ], - "index": 535 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "4.4.3. Proprietà elettrochimiche dei copolimeri lienari", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 536, - "anchor": "_Toc242438085", - "is_numbered_style": false, - "level": 3 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Definita la metodologia di indagine, l'analisi dei risultati è partita dallo studio dei copolimeri lineari precursori. L'analisi di questi precursori risulta di fondamentale importanza per valutare il comportamento redox dello scheletro coniugato puro, svincolando la lettura dei dati dalle potenziali variazioni conformazionali o dagli effetti di ingombro sterico indotti dai successivi passaggi di funzionalizzazione." - } - ] - } - ], - "index": 537 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'obiettivo primario di questa sezione è, quindi, esaminare in modo sistematico come la frazione reale di unità DPP incorporate lungo la catena polimerica, moduli attivamente l'architettura energetica del sistema. Studiando la risposta voltammetrica di questa serie di copolimeri, è possibile tracciare in modo accurato l'evoluzione dei potenziali termodinamici di iniezione ed estrazione di carica, quantificando l'impatto strutturale del monomero sull'ampiezza del bandgap elettrochimico e sul posizionamento dei livelli HOMO e LUMO." - } - ] - } - ], - "index": 538 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I parametri termodinamici e i livelli energetici degli orbitali di frontiera, estratti dai voltammogrammi ciclici per tutti i copolimeri di partenza indagati, sono raccolti nella " - }, - { - "type": "text", - "content": "Tabella 13", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ". Questa raccolta dati fornisce la base quantitativa essenziale per lo sviluppo delle successive correlazioni." - } - ] - } - ], - "index": 539 - }, - { - "type": "table", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tabella 13 – dati voltammetrici dei copolimeri sintetizzati", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 540, - "type": "table_caption" - }, - { - "lines": [ - { - "spans": [ - { - "type": "table", - "html": "

Polimero

% reale DPP

(V)

(V)

HOMO (eV)

LUMO (eV)

Bandgap (eV)

3a

25

0,238

-0,732

-5,038

-4,068

0,970

3b

32

0,054

-1,262

-4,854

-3,538

1,316

3c

35

0,0006

-1,372

-4,799

-3,428

1,371

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Frazione reale DPPSeries1
0.250.97
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0.351.3714000000000002
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Frazione reale DPPE picco anodicoE picco catodico
0.250.38200000000000001-1.02
0.320.2-1.8129999999999999
0.350.22800000000000001-1.633
", - "image_path": "" - } - ] - } - ], - "index": 549, - "type": "chart_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 72 - correlazione tra E", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "picco", - "style": [ - "italic", - "subscript" - ] - }, - { - "type": "text", - "content": " e frazione reale di DPP nei copolimeri sintetizzati", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 550, - "type": "chart_caption" - } - ], - "index": 549 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La variazione più marcata si osserva a carico del processo di riduzione (drogaggio di tipo n): all'aumentare della frazione di DPP, il potenziale di picco catodico subisce un drastico spostamento verso valori significativamente più negativi. Passando dal copolimero con il contenuto di DPP più basso (25%), con " - }, - { - "type": "inline_equation", - "content": "E_{pc}" - }, - { - "type": "text", - "content": " a circa – 1 V, ai materiali con frazioni superiori (32-35%), il picco si sposta nella regione compresa tra – 1.6 V e – 1.8 V. Questa traslazione indica che il processo di inserzione di elettroni diventa termodinamicamente più sfavorito all'aumentare della percentuale di DPP, richiedendo sovratensioni progressivamente maggiori per innescare la formazione delle specie radical-anioniche." - } - ] - } - ], - "index": 551 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Per quanto riguarda il processo di ossidazione (drogaggio di tipo p), l'impatto del contenuto di DPP risulta meno drastico ma ugualmente rilevabile. Il potenziale di picco anodico (" - }, - { - "type": "inline_equation", - "content": "E_{pa}" - }, - { - "type": "text", - "content": ") mostra un moderato spostamento verso valori meno positivi, passando da circa 0.4 V per il polimero a minor contenuto di DPP a valori stabilizzati attorno a 0.2/0.25 V per le frazioni maggiori." - } - ] - } - ], - "index": 552 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Analizzando il sistema nel suo complesso, l'effetto combinato di queste due traslazioni si traduce in un allargamento della separazione tra i picchi all'aumentare della percentuale di DPP incorporata. Questa divergenza progressiva tra i potenziali di picco è coerente con l'aumento lineare del band gap elettrochimico discusso precedentemente." - } - ] - } - ], - "index": 553 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tuttavia, a causa dell'irreversibilità dei processi e delle cinetiche di degradazione associate ai potenziali di picco, un quadro energetico più accurato si ottiene esaminando i potenziali di onset, i quali rappresentano in modo più rigoroso i potenziali di attivazione termodinamica." - } - ] - } - ], - "index": 554 - }, - { - "type": "chart", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "chart", - "content": "
Frazione reale DPPEonset anodicoE onset catodico
0.250.23799999999999999-0.73199999999999998
0.325.3800000000000001E-2-1.262
0.35-5.9999999999999995E-4-1.3720000000000001
", - "image_path": "" - } - ] - } - ], - "index": 555, - "type": "chart_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 73 - correlazione tra E", - "style": [ - "italic" - ] - }, - { - "type": "text", - "content": "onset ", - "style": [ - "italic", - "subscript" - ] - }, - { - "type": "text", - "content": "e frazione reale di DPP nei copolimeri sintetizzati", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 556, - "type": "chart_caption" - } - ], - "index": 555 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Come illustrato in " - }, - { - "type": "text", - "content": "Figura 73", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", l'andamento dei potenziali di onset in funzione della frazione di DPP rispecchia fedelmente le tendenze osservate per i potenziali di picco. Il potenziale di onset catodico (" - }, - { - "type": "inline_equation", - "content": "E_{onset}^{red}" - }, - { - "type": "text", - "content": "), indicativo dell'energia del LUMO, mostra uno spostamento pronunciato verso valori più negativi, passando da circa – 0.75 V per il copolimero a basso contenuto di DPP a valori prossimi a – 1.4 V per le frazioni maggiori. Parallelamente, il potenziale di onset anodico (" - }, - { - "type": "inline_equation", - "content": "E_{onset}^{ox}" - }, - { - "type": "text", - "content": "), correlato all'energia dell'HOMO, subisce una lieve traslazione verso potenziali meno positivi (da circa 0.25 V a quasi 0 V). La progressiva separazione tra " - }, - { - "type": "inline_equation", - "content": "E_{onset}^{ox}" - }, - { - "type": "text", - "content": " ed " - }, - { - "type": "inline_equation", - "content": "E_{onset}^{red}" - }, - { - "type": "text", - "content": " all'aumentare dell'unità DPP conferma l'allargamento del bandgap, dimostrando come la composizione macromolecolare agisca in modo sistematico sui livelli energetici di frontiera del materiale." - } - ] - } - ], - "index": 557 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "A ulteriore conferma dell'impatto strutturale dell'unità dichetopirrolopirrolo, risulta logico un confronto con il comportamento elettrochimico del poli(3-esiltiofene) (P3HT) omopolimero." - } - ] - } - ], - "index": 558 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il P3HT è un sistema marcatamente elettron-ricco che mostra un processo di ossidazione (p-doping) a potenziali accessibili, ma non presenta contributi faradici significativi a potenziali minori per quanto riguarda i processi di riduzione (n-doping) all'interno della consueta finestra di stabilità dei solventi organici. Al contrario, nei copolimeri qui sintetizzati, l'introduzione del DPP modifica radicalmente la risposta voltammetrica. Agendo da forte porzione elettron-attrattrice all'interno di un'architettura coniugata di tipo donatore-accettore, l'unità DPP stabilizza marcatamente il livello LUMO del sistema. Questa stabilizzazione rende termodinamicamente favorevole l'iniezione di elettroni, giustificando la comparsa delle evidenti onde catodiche a potenziali minori che risultano invece assenti nel P3HT puro. Tale marcato abbassamento del LUMO, accoppiato alla modulazione del livello HOMO governata principalmente dai segmenti di 3-esiltiofene, costituisce il fattore chiave che determina il restringimento del bandgap rispetto all'omopolimero di riferimento." - } - ] - } - ], - "index": 559 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Nel complesso, i risultati dell'indagine voltammetrica attestano la validità del design molecolare adottato: l'elevata sistematicità con cui la composizione influenza la risposta termodinamica convalida l'approccio sintetico come strumento efficace per l'ingegnerizzazione del materiale, definendo un protocollo per la sua ottimizzazione in vista di future applicazioni in ambito optoelettronico." - } - ] - } - ], - "index": 560 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "4.4.4. Effetto del design bottle brush", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 561, - "anchor": "_Toc242438086", - "is_numbered_style": false, - "level": 3 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Dopo aver caratterizzato il comportamento optoelettronico dello scheletro coniugato di base, l'analisi è proseguita valutando l'impatto dell'architettura macromolecolare complessa." - } - ] - } - ], - "index": 562 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "I parametri termodinamici ed energetici finali, calcolati per l'intera serie di composti sintetizzati, sono riassunti in modo sistematico nella " - }, - { - "type": "text", - "content": "Tabella 14", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "." - } - ] - } - ], - "index": 563 - }, - { - "type": "table", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tabella 14 - dati voltammetrici dei polimeri sintetizzati", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 564, - "type": "table_caption" - }, - { - "lines": [ - { - "spans": [ - { - "type": "table", - "html": "

Polimero

(V)

(V)

HOMO (eV)

LUMO (eV)

Bandgap (eV)

3.1.b

-0,183

-1,22

-4,617

-3,580

1,037

3.2.b

-0,175

-1,273

-4,625

-3,527

1,098

3.3.b

-0,17

-1,202

-4,630

-3,598

1,032

3.1.c

-0,0259

-1,547

-4,774

-3,253

1,521

3.2.c

-0,112

-1,531

-4,688

-3,269

1,419

3.3.c

-0,321

-1,25

-4,479

-3,550

0,929

" - } - ] - } - ], - "index": 565, - "type": "table_body" - } - ], - "index": 565 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Dal confronto tra questi dati e quelli dei precursori lineari discussi nel paragrafo XX (XX), è possibile valutare l'impatto dell'innesto delle catene laterali di policaprolattone (PCL) sulle proprietà optoelettroniche del materiale." - } - ] - } - ], - "index": 566 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Innanzitutto, l'analisi evidenzia che i copolimeri bottle-brush mantengono la caratteristica elettroattività dello scheletro coniugato. Questo comportamento dimostra che i processi di ossido-riduzione avvengono coerentemente a carico del core a base di DPP e 3HT, mentre i rami alifatici fungono da matrice dielettrica circostante." - } - ] - } - ], - "index": 567 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Tuttavia, la transizione verso un'architettura macromolecolare più complessa induce delle modulazioni evidenti nei livelli energetici di frontiera. Osservando i valori di HOMO e LUMO, l'introduzione delle ingombranti catene laterali modifica l'assetto energetico rispetto ai polimeri lineari di partenza. Questo effetto si riflette in modo diretto sull'ampiezza del bandgap elettrochimico finale. Tali variazioni possono essere attribuite agli effetti di ingombro sterico indotti dai rami di PCL: la loro presenza volumetrica influenza il grado di coplanarità locale dello scheletro coniugato, alterando di conseguenza l'estensione effettiva della delocalizzazione elettronica lungo la catena principale. Nonostante queste fluttuazioni conformazionali, i valori di bandgap dei copolimeri bottle-brush si attestano in un range compreso tra 0,929 eV e 1,521 eV. Il mantenimento di queste ampiezze conferma che l'ingegnerizzazione dell'architettura mediante PCL non compromette le spiccate potenzialità optoelettroniche del sistema coniugato originario." - } - ] - } - ], - "index": 568 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "4.5. Caratterizzazione spettroscopica allo stato solido", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 569, - "anchor": "_Toc242438087", - "is_numbered_style": false, - "level": 2 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Lo studio delle proprietà ottiche allo stato solido rappresenta un passaggio fondamentale nella caratterizzazione dei materiali polimerici coniugati, specialmente in ottica di una possibile integrazione in dispositivi optoelettronici. Mentre le misurazioni effettuate in soluzione diluita permettono di indagare le proprietà fotofisiche della singola catena polimerica isolata e solvatata, l'analisi allo stato solido rivela il comportamento del materiale nelle sue condizioni operative. In questo stato, la vicinanza tra le macromolecole porta all'instaurarsi di forti interazioni intermolecolari, che alterano significativamente i livelli energetici di banda e, di conseguenza, i processi di assorbimento ed emissione fotonica." - } - ] - } - ], - "index": 570 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Negli spettri di assorbimento UV-Vis registrati allo stato solido, la limitata mobilità conformazionale e il forte impaccamento delle catene inducono generalmente una maggiore planarizzazione dello scheletro coniugato. Rispetto agli spettri in soluzione, questo fenomeno si traduce in una delocalizzazione elettronica più estesa lungo il backbone polimerico, portando a un aumento della lunghezza di coniugazione effettiva. Macroscopicamente, tale effetto genera un tipico spostamento batocromo del massimo di assorbimento e, in molti casi, la comparsa di una struttura vibronica più risolta, indice di un elevato grado di ordine strutturale locale." - } - ] - } - ], - "index": 571 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La tipologia di aggregazione supramolecolare detta le regole di transizione elettronica. Secondo la teoria dell'accoppiamento eccitonico di Kasha, l'impaccamento delle catene coniugate può avvenire prevalentemente secondo due geometrie: gli aggregati di tipo H (impaccamento face-to-face, in cui prevalgono le interazioni π-π laterali) e gli aggregati di tipo J (impaccamento head-to-tail). Nei polimeri coniugati, le forti interazioni π-π favoriscono frequentemente la formazione di aggregati H, i quali presentano una transizione otticamente permessa verso lo stato eccitonico a maggiore energia." - }, - { - "type": "text", - "content": "58", - "style": [ - "superscript" - ] - } - ] - } - ], - "index": 572 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Queste dinamiche di aggregazione hanno ripercussioni molto evidenti sulle proprietà di emissione allo stato solido. Il fenomeno più comunemente osservato nei sistemi π-coniugati altamente planari è l'estinzione dell'emissione causata dall'aggregazione (ACQ). La forte vicinanza tra gli anelli aromatici e la formazione di aggregati H, favoriscono il rilassamento non radiativo degli eccitoni attraverso la formazione di eccimeri o il trasferimento di energia verso siti di smorzamento (difetti conformazionali o trappole energetiche). Di conseguenza, le rese quantiche di fluorescenza allo stato solido subiscono un drastico abbattimento rispetto a quelle misurate in soluzione." - }, - { - "type": "text", - "content": "59", - "style": [ - "superscript" - ] - } - ] - } - ], - "index": 573 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Nei copolimeri alternati a donatore-accettore (D-A), la struttura è ulteriormente arricchita dalla presenza della banda di trasferimento di carica intramolecolare (ICT). L'impaccamento solido riduce le distanze intermolecolari, facilitando anche fenomeni di trasferimento di carica intermolecolare. In sistemi che presentano forti cromofori elettron-accettori e unità elettron-donatrici, come i derivati tiofenici, la tendenza all’impaccamento intermolecolare ed alla cristallizzazione è notevole. Per modulare questi effetti e prevenire un quenching della luminescenza, l'introduzione di ingombri sterici mirati, come catene alchiliche ramificate, innesti polimerici laterali o architetture bottle-brush, diventa una strategia cruciale. Tali modifiche strutturali agiscono da spaziatori fisici: pur mantenendo la coniugazione elettronica sul backbone principale, ostacolano l'eccessivo avvicinamento dei piani π, limitando la formazione di aggregati H non radiativi e preservando in parte le proprietà emissive del materiale." - } - ] - } - ], - "index": 574 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Al fine di indagare l'intricata correlazione tra la struttura supramolecolare e il comportamento fotofisico del sistema sintetizzato, è stata condotta un'analisi spettroscopica combinata in assorbimento UV-Vis e in emissione allo stato solido su uno dei campioni rappresentativi, il polimero bottle brush 3.2.b (" - }, - { - "type": "text", - "content": "Figura 74", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ")." - } - ] - } - ], - "index": 575 - }, - { - "type": "image", - "blocks": [ - { - "lines": [ - { - "spans": [ - { - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/15f01405-8bac-456c-90f5-57cdb8e72d5a/35b98a0a92f2091382ef285d4a9a446a02d3c0ccaff98eeb82d17f4db843ea23.png" - } - ] - } - ], - "index": 576, - "type": "image_body" - }, - { - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Figura 74 - confronto tra spettri UV-Vis (in nero) ed emissione (in rosso) del polimero 3.2.b in soluzione (linea continua) e allo stato solido (linea tratteggiata)", - "style": [ - "italic" - ] - } - ] - } - ], - "index": 577, - "type": "image_caption" - } - ], - "index": 576 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L'analisi comparativa delle proprietà ottiche in soluzione liquida (LS) e allo stato solido (SS) permette di evidenziare l'effetto dell'impaccamento macromolecolare sulle transizioni elettroniche del materiale sintetizzato. Osservando i profili di assorbimento, in soluzione il polimero presenta una banda principale con un massimo di assorbimento centrato a circa 550 nm. Passando allo stato solido, il profilo di assorbimento subisce un significativo allargamento e un marcato spostamento batocromo, riposizionando il massimo di transizione nell'intervallo tra 570 e 580 nm, unitamente a una variazione dell'intensità relativa della spalla vibronica a energie maggiori. Questo slittamento verso lunghezze d'onda superiori è attribuibile alla planarizzazione del backbone coniugato indotta dai vincoli conformazionali dello stato solido, la quale favorisce un'estensione della lunghezza di coniugazione effettiva rispetto alle catene solvatate." - } - ] - } - ], - "index": 578 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Le variazioni più drastiche si riscontrano tuttavia nei profili di emissione. Lo spettro di emissione in soluzione mostra una banda stretta e strutturata, con un massimo a circa 560-565 nm e un ridotto spostamento di Stokes, caratteristico del rilassamento radiativo da singola catena isolata. Al contrario, l'emissione allo stato solido si presenta notevolmente allargata e subisce un elevato red-shift, esibendo un massimo centrato intorno a 650-660 nm. Questo notevole incremento dello spostamento di Stokes tra l'assorbimento e l'emissione allo stato solido (circa 80-90 nm) è probabilmente legato a un maggiore ingombro delle catene polimeriche, che obbliga gli anelli aromatici ad assumere torsioni maggiori, e costituisce al contempo una chiara evidenza della forte aggregazione intermolecolare. Tali evidenze spettrali indicano che, a seguito della fotoeccitazione, l'energia migra efficientemente verso siti a minore energia generati dalla forte vicinanza tra i piani coniugati (interazioni π-π), portando al rilassamento radiativo prevalentemente da stati aggregati o specie eccimeriche, piuttosto che dalle singole catene polimeriche non interagenti." - } - ] - } - ], - "index": 579 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In conclusione, le marcate variazioni spettrali osservate confermano l'instaurarsi di un forte riarrangiamento strutturale allo stato solido, un aspetto determinante che definisce l'effettivo profilo fotofisico del materiale." - } - ] - } - ], - "index": 580 - }, - { - "type": "title", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Conclusioni", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 581, - "anchor": "_Toc242438088", - "is_numbered_style": true, - "level": 1, - "section_number": "5" - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Il presente lavoro di tesi si è prefissato l’obiettivo primario di progettare, sintetizzare e caratterizzare nuove architetture macromolecolari semiconduttrici ed emissive ad architettura a spazzola (bottle brush), al fine di superare una delle più gravicriticità dei materiali π-coniugati nell’ambito della soft optoelectronics: il fenomeno dello spegnimento dell'emissione indotto da aggregazione (Aggregation-Caused Quenching, ACQ). La naturale propensione dei sistemi planari coniugati a instaurare intense interazioni supramolecolari di π-π stacking porta infatti a una drastica dissipazione non radiativa dell’energia eccitonica allo stato solido. Per ovviare a questo limite, la strategia adottata si è basata sulla realizzazione di copolimeri bottle brush, nei quali l'accrescimento di catene polimeriche laterali flessibili lungo uno scheletro elettro- e fotoattivo è stato sfruttato come spaziatore sterico per modulare l'impaccamento intermolecolare, preservando al contempo le proprietà elettroniche del backbone." - } - ] - } - ], - "index": 582 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Dal punto di vista sintetico, il percorso intrapreso ha dimostrato la piena efficacia e riproducibilità di una strategia basata sull'impiego di monomeri ortogonali e multifunzionali derivati dal dichetopirrolopirrolo (DPP). In primo luogo, la reazione di ciclizzazione tra il " - }, - { - "type": "text", - "content": "2", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "-cianotiofene e il diisopropil succinato ha consentito di isolare con successo il fluoroforo tetraciclico " - }, - { - "type": "text", - "content": "1", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ". La successiva funzionalizzazione mediante " - }, - { - "type": "inline_equation", - "content": "N" - }, - { - "type": "text", - "content": "-alchilazione nucleofila con 6-bromo-" - }, - { - "type": "text", - "content": "1", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "-esanolo ha portato all’ottenimento del monomero chiave bis-alchilato (composto " - }, - { - "type": "text", - "content": "2", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": "), confermato per via spettroscopica (-NMR e FT-IR). Tale monomero ha esibito la duplice funzionalità ricercata: la presenza degli eterocicli tiofenici ha fornito i siti reattivi per l'accrescimento della catena principale semiconduttrice, mentre i gruppi ossidrilici primari terminali hanno svolto il ruolo di iniziatori indipendenti per la successiva fase di innesto. La sintesi dello scheletro polimerico coniugato è stata condotta mediante polimerizzazione ossidativa diretta mediata da cloruro ferrico in presenza di nitrometano, accoppiando il monomero di DPP con il 3-esiltiofene (3HT). Questo approccio si è rivelato particolarmente vantaggioso rispetto ai canonici accoppiamenti incrociati mediati da palladio, eliminando la necessità di stadi di pre-funzionalizzazione e operando in condizioni termodinamiche blande. La sintesi di tre differenti copolimeri statistici a rapporto co-monomerico variabile (" - }, - { - "type": "text", - "content": "3a", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ", " - }, - { - "type": "text", - "content": "3b", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " e " - }, - { - "type": "text", - "content": "3c", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": ") ha confermato la versatilità della metodica, permettendo di ottenere materiali processabili con pesi molecolari compresi tra circa 1400 e 2150 Da e un intervallo di lavorabilità termica adeguato, caratterizzato da transizioni vetrose intorno a – 10 °C e temperature di fusione superiori a 110 °C." - } - ] - } - ], - "index": 583 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "L’accrescimento delle architetture bottle brush a partire dai macroiniziatori " - }, - { - "type": "text", - "content": "3b", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " e " - }, - { - "type": "text", - "content": "3c", - "style": [ - "bold" - ] - }, - { - "type": "text", - "content": " è stato realizzato mediante polimerizzazione ad apertura d'anello (ROP) dell' " - }, - { - "type": "inline_equation", - "content": "\\varepsilon" - }, - { - "type": "text", - "content": "-caprolattone, catalizzata da ottanoato di stagno. Attraverso la modulazione del rapporto molare tra monomero ciclico e siti ossidrilici pendenti, sono state sintetizzate con successo due serie di copolimeri a spazzola con catene laterali di PCL a pesi molecolari nominali crescenti (1500, 5000 e 10000 Da). L'avvenuta reazione di innesto è stata verificata tramite FT-IR, registrando la completa scomparsa della banda associata agli ossidrili terminali e la concomitante comparsa dell'intenso assorbimento carbonilico estereo del PCL a circa " - }, - { - "type": "inline_equation", - "content": "1720 cm^{-1}" - }, - { - "type": "text", - "content": ". L'indagine condotta mediante cromatografia a permeazione di gel (GPC) ha evidenziato indici di dispersità contenuti (1.23–1.52). Inoltre, la marcata contrazione del volume idrodinamico in soluzione rilevata rispetto ai pesi teorici lineari ha costituito una prova dell'ottenimento di macromolecole ramificate a densità elevata e struttura altamente compatta. Dal punto di vista termico, il comportamento dei sistemi bottle brush si è dimostrato governato dalla fase semicristallina dominante delle catene laterali di PCL, garantendo un profilo termico omogeneo e indipendente dalle minime oscillazioni della catena principale." - } - ] - } - ], - "index": 584 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "La caratterizzazione ottica in soluzione ha evidenziato che la funzionalizzazione sterica non perturba l'integrità elettronica del core dichetopirrolopirrolico: i massimi di assorbimento (544–554 nm) e di emissione (557–564 nm), unitamente a valori di Stokes shift costantemente contenuti (8–14 nm), hanno confermato la conservazione dell'assetto planare del cromoforo e la minima riorganizzazione strutturale tra stato fondamentale ed eccitato. Al contrario, le indagini spettroscopiche condotte allo stato solido su film sottili (esemplificate sul campione 3.2b) hanno fornito indicazioni determinanti: lo spostamento batocromo dell'assorbimento (fino a 570–580 nm) e l'allargamento spettrale dell'emissione, con un marcato red-shift centrato a circa 650–660 nm, hanno dimostrato come l'impaccamento supramolecolare promuova la migrazione dell'eccitone verso stati aggregati a minore energia. Nonostante l'insorgenza di tali riarrangiamenti, l'architettura bottle brush ha consentito il mantenimento di un'apprezzabile emissione nel rosso, attenuando i percorsi di disattivazione non radiativa totale tipici dell'ACQ non controllato." - } - ] - } - ], - "index": 585 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Infine, l'approfondita indagine elettrochimica condotta mediante ciclovoltammetria ha fornito riscontri fondamentali circa le proprietà semiconduttrici e la struttura a bande dei materiali. Sebbene i polimeri esibiscano un meccanismo di trasferimento di carica irreversibile di tipo elettrochimico-chimico indotto dall'elevata reattività dei cationi e anioni radicalici all'interfaccia elettrodica, l'estrapolazione rigorosa dei potenziali di onset ha consentito di determinare con precisione la posizione dei livelli energetici HOMO e LUMO e l'ampiezza del bandgap elettrochimico. L'analisi comparativa ha evidenziato una correlazione lineare (" - }, - { - "type": "inline_equation", - "content": "R^{2}=0.9719" - }, - { - "type": "text", - "content": ") tra la percentuale reale di DPP incorporata e l'allargamento del bandgap (da 3.42 eV a oltre 4.30 eV), guidata principalmente da uno spostamento del potenziale di riduzione catodica verso valori progressivamente più negativi. Tale sistematicità dimostra che la composizione monomerica funge da eccellente parametro di controllo per calibrare finemente i livelli elettronici di frontiera." - } - ] - } - ], - "index": 586 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "In conclusione, i risultati conseguiti nel presente lavoro di tesi confermano la validità del design macromolecolare proposto: l'approccio ortogonale basato su scheletri semiconduttori DPP-3HT modificati mediante catene laterali di PCL consente di combinare proprietà elettrochimiche modulabili e capacità emissiva allo stato solido." - } - ] - } - ], - "index": 587 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "Bibliografia", - "style": [ - "bold" - ] - } - ] - } - ], - "index": 588 - }, - { - "type": "text", - "lines": [ - { - "spans": [ - { - "type": "text", - "content": "2.\tShaikh, S. A. L. 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L'architettura bottle brush finale è stata realizzata tramite", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 395, - 523, - 405 - ], - "spans": [ - { - "bbox": [ - 70, - 395, - 523, - 405 - ], - "type": "text", - "content": "polimerizzazione ad apertura d'anello (ROP) dell'ε-caprolattone, facendo crescere catene", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 416, - 523, - 425 - ], - "spans": [ - { - "bbox": [ - 70, - 416, - 523, - 425 - ], - "type": "text", - "content": "laterali flessibili di policaprolattone (PCL) con diversi pesi molecolari (1500, 5000 e 10000", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 68, - 434, - 92, - 449 - ], - "spans": [ - { - "bbox": [ - 68, - 434, - 92, - 449 - ], - "type": "text", - "content": "Da).", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 457, - 523, - 467 - ], - "spans": [ - { - "bbox": [ - 70, - 457, - 523, - 467 - ], - "type": "text", - "content": "Le analisi spettroscopiche (1H-NMR e FT-IR) e cromatografiche (GPC) hanno confermato il", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 478, - 523, - 487 - ], - "spans": [ - { - "bbox": [ - 70, - 478, - 523, - 487 - ], - "type": "text", - "content": "successo della sintesi e l'ottenimento di macromolecole ramificate ad alta densità strutturale. La", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 498, - 523, - 507 - ], - "spans": [ - { - "bbox": [ - 70, - 498, - 523, - 507 - ], - "type": "text", - "content": "caratterizzazione ottica ha dimostrato che, mentre in soluzione il core di DPP mantiene intatta", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 519, - 523, - 528 - ], - "spans": [ - { - "bbox": [ - 70, - 519, - 523, - 528 - ], - "type": "text", - "content": "la sua integrità elettronica, allo stato solido l'introduzione delle catene laterali di PCL agisce", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 538, - 523, - 550 - ], - "spans": [ - { - "bbox": [ - 69, - 538, - 523, - 550 - ], - "type": "text", - "content": "efficacemente come spaziatore sterico. Questo ingombro limita l'eccessivo impaccamento", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 560, - 523, - 570 - ], - "spans": [ - { - "bbox": [ - 70, - 560, - 523, - 570 - ], - "type": "text", - "content": "intermolecolare, permettendo al materiale di conservare un'apprezzabile emissione nel rosso e", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 580, - 418, - 590 - ], - "spans": [ - { - "bbox": [ - 70, - 580, - 418, - 590 - ], - "type": "text", - "content": "attenuando così i percorsi di disattivazione non radiativa tipici dell'ACQ", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 602, - 523, - 612 - ], - "spans": [ - { - "bbox": [ - 70, - 602, - 523, - 612 - ], - "type": "text", - "content": "Infine, le indagini elettrochimiche condotte tramite ciclovoltammetria hanno introdotto lo", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 622, - 523, - 632 - ], - "spans": [ - { - "bbox": [ - 70, - 622, - 523, - 632 - ], - "type": "text", - "content": "studio delle proprietà semiconduttrici dei materiali sintetizzati. 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Optical characterization demonstrated that, while in solution the DPP core keeps its", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 478, - 523, - 487 - ], - "spans": [ - { - "bbox": [ - 70, - 478, - 523, - 487 - ], - "type": "text", - "content": "electronic integrity intact, in the solid state the introduction of the PCL side chains acts", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 497, - 523, - 509 - ], - "spans": [ - { - "bbox": [ - 70, - 497, - 523, - 509 - ], - "type": "text", - "content": "effectively as a steric spacer. This steric hindrance limits the excessive intermolecular packing,", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 518, - 522, - 528 - ], - "spans": [ - { - "bbox": [ - 69, - 518, - 522, - 528 - ], - "type": "text", - "content": "allowing the material to retain an appreciable emission in the red and thus attenuating the non", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 539, - 300, - 550 - ], - "spans": [ - { - "bbox": [ - 69, - 539, - 300, - 550 - ], - "type": "text", - "content": "radiative deactivation pathways typical of ACQ.", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 560, - 522, - 569 - ], - "spans": [ - { - "bbox": [ - 70, - 560, - 522, - 569 - ], - "type": "text", - "content": "Finally, electrochemical investigations conducted via cyclic voltammetry were performed to", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 580, - 524, - 592 - ], - "spans": [ - { - "bbox": [ - 69, - 580, - 524, - 592 - ], - "type": "text", - "content": "assess the semiconducting properties of the synthesized materials. 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Introduzione .... 1\n1.1. Dichetopirrolopirroli .... 1\n1.1.1. Storia e sintesi .... 1\n1.1.2. Struttura e reattività .... 10\n1.2. Fluorescenza.... 23\n1.2.1. Shift di Stokes.... 26\n1.2.2. Resa quantica.... 27\n1.2.3. Tempi di vita.... 27\n1.3. Utilizzo di fluorofori in materiali polimerici.... 29\n1.4. Applicazioni.... 32\n2. Scopo.... 36\n3. Procedure sperimentali.... 38\n3.1. Materiali e metodi.... 38\n3.2. Sintesi e procedure.... 39\n3.3. Principi teorici della ciclovoltammetria.... 43\n3.4. Procedure sperimentali delle analisi voltammetriche.... 45\n4. Discussione dei risultati.... 47\n4.1. Dichetopirrolopirroli.... 47\n4.2. Copolimeri coniugati.... 57\n4.3. Polimeri bottle brush.... 68\n4.4. Ciclovoltammetrie.... 80\n4.4.1. Ciclovoltammetrie su polimeri elettroattivi.... 80\n4.4.2. Metodologie di analisi voltammetrica.... 81\n4.4.3. Proprietà elettrochimiche dei copolimeri lienari.... 86\n4.4.4. Effetto del design bottle brush.... 90\n4.5. Caratterizzazione spettroscopica allo stato solido.... 92\n5. Conclusioni.... 95" - } - ] - } - ], - "index": 1 - } - ], - "discarded_blocks": [], - "page_size": [ - 595, - 841 - ], - "page_idx": 4, - "para_blocks": [ - { - "bbox": [ - 67, - 70, - 135, - 88 - ], - "type": "title", - "angle": 0, - "index": 0, - "lines": [ - { - "bbox": [ - 69, - 72, - 133, - 86 - ], - "spans": [ - { - "bbox": [ - 69, - 72, - 133, - 86 - ], - "type": "text", - "content": "Sommario", - "score": 1.0 - } - ] - } - ], - "level": 2 - }, - { - "bbox": [ - 67, - 96, - 526, - 754 - ], - "type": "text", - "angle": 0, - "lines": [ - { - "bbox": [ - 67, - 96, - 526, - 754 - ], - "spans": [ - { - "bbox": [ - 67, - 96, - 526, - 754 - ], - "type": "text", - "content": "1. Introduzione .... 1\n1.1. Dichetopirrolopirroli .... 1\n1.1.1. Storia e sintesi .... 1\n1.1.2. Struttura e reattività .... 10\n1.2. Fluorescenza.... 23\n1.2.1. Shift di Stokes.... 26\n1.2.2. Resa quantica.... 27\n1.2.3. Tempi di vita.... 27\n1.3. Utilizzo di fluorofori in materiali polimerici.... 29\n1.4. Applicazioni.... 32\n2. Scopo.... 36\n3. Procedure sperimentali.... 38\n3.1. Materiali e metodi.... 38\n3.2. Sintesi e procedure.... 39\n3.3. Principi teorici della ciclovoltammetria.... 43\n3.4. Procedure sperimentali delle analisi voltammetriche.... 45\n4. Discussione dei risultati.... 47\n4.1. Dichetopirrolopirroli.... 47\n4.2. Copolimeri coniugati.... 57\n4.3. Polimeri bottle brush.... 68\n4.4. Ciclovoltammetrie.... 80\n4.4.1. Ciclovoltammetrie su polimeri elettroattivi.... 80\n4.4.2. Metodologie di analisi voltammetrica.... 81\n4.4.3. Proprietà elettrochimiche dei copolimeri lienari.... 86\n4.4.4. Effetto del design bottle brush.... 90\n4.5. Caratterizzazione spettroscopica allo stato solido.... 92\n5. 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401, - 524, - 414 - ], - "spans": [ - { - "bbox": [ - 70, - 401, - 524, - 414 - ], - "type": "text", - "content": "attaccare un elettrofilo. 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Recentemente Würthner ed i suoi collaboratori hanno", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 488, - 524, - 501 - ], - "spans": [ - { - "bbox": [ - 69, - 488, - 524, - 501 - ], - "type": "text", - "content": "dimostrato che la reazione SNAr dei DPP può essere eseguita anche utilizzando l’1-fluoro-2-", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 505, - 333, - 521 - ], - "spans": [ - { - "bbox": [ - 69, - 505, - 333, - 521 - ], - "type": "text", - "content": "nitro-4-(trifluorometil)benzene come agente arilante.23", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - }, - { - "bbox": [ - 67, - 549, - 222, - 564 - ], - "type": "title", - "angle": 0, - "index": 4, - "lines": [ - { - "bbox": [ - 70, - 550, - 219, - 562 - ], - "spans": [ - { - "bbox": [ - 70, - 550, - 219, - 562 - ], - "type": "text", - "content": "Reazioni sugli anelli aromatici", - "score": 1.0 - } - ] - } - ], - "level": 2 - }, - { - "bbox": [ - 66, - 569, - 527, - 668 - ], - "type": "text", - "angle": 0, - "index": 5, - "lines": [ - { - "bbox": [ - 68, - 569, - 524, - 584 - ], - "spans": [ - { - "bbox": [ - 68, - 569, - 524, - 584 - ], - "type": "text", - "content": "Sebbene non strettamente parte del core dichetopirrolopirrolico, la maggior parte dei DPP", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 68, - 591, - 525, - 604 - ], - "spans": [ - { - "bbox": [ - 68, - 591, - 525, - 604 - ], - "type": "text", - "content": "presenti in letteratura contengono sostituenti aromatici derivanti dai benzonitrili di partenza e", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 613, - 523, - 624 - ], - "spans": [ - { - "bbox": [ - 70, - 613, - 523, - 624 - ], - "type": "text", - "content": "vengono quindi considerati parte integrante della struttura. I sostituenti arilici, in particolare,", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 68, - 632, - 524, - 646 - ], - "spans": [ - { - "bbox": [ - 68, - 632, - 524, - 646 - ], - "type": "text", - "content": "possono subire reazioni tipiche dei composti aromatici, come sostituzioni elettrofile aromatiche", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 68, - 652, - 105, - 667 - ], - "spans": [ - { - "bbox": [ - 68, - 652, - 105, - 667 - ], - "type": "text", - "content": "(SeAr).", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - }, - { - "bbox": [ - 66, - 672, - 527, - 772 - ], - "type": "text", - "angle": 0, - "index": 6, - "lines": [ - { - "bbox": [ - 70, - 674, - 524, - 686 - ], - "spans": [ - { - "bbox": [ - 70, - 674, - 524, - 686 - ], - "type": "text", - "content": "Ad esempio, il DPP ottenuto mediante l’utilizzo di benzonitrile (3), può essere solfonato con", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 694, - 524, - 708 - ], - "spans": [ - { - "bbox": [ - 69, - 694, - 524, - 708 - ], - "type": "text", - "content": "acido solforico fumante, ottenendo il DPP 26 contenente gruppi solfonici nelle posizioni para", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 715, - 523, - 729 - ], - "spans": [ - { - "bbox": [ - 69, - 715, - 523, - 729 - ], - "type": "text", - "content": "degli anelli benzenici (Figura 20). Il DPP 3 può reagire anche con il bromo ed il cloro gassosi,", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 68, - 735, - 525, - 750 - ], - "spans": [ - { - "bbox": [ - 68, - 735, - 525, - 750 - ], - "type": "text", - "content": "producendo due molecole completamente diverse: mediante l’uso di bromo si provoca una", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 756, - 524, - 769 - ], - "spans": [ - { - "bbox": [ - 69, - 756, - 524, - 769 - ], - "type": "text", - "content": "sostituzione elettrofila aromatica ottenendo il DPP 27 para-dibromurato, mentre utilizzando il", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 73, - 524, - 84 - ], - "spans": [ - { - "bbox": [ - 69, - 73, - 524, - 84 - ], - "type": "text", - "content": "cloro si ottiene il prodotto in cui quest’ultimo viene addizionato ai doppi legami dell’unità", - "score": 1.0, - "cross_page": true - } - ] - }, - { - "bbox": [ - 69, - 92, - 524, - 105 - ], - "spans": [ - { - "bbox": [ - 69, - 92, - 524, - 105 - ], - "type": "text", - "content": "centrale di DPP (28). Sebbene la bromurazione del DPP 3 abbia una buona resa, superiore", - "score": 1.0, - "cross_page": true - } - ] - }, - { - "bbox": [ - 70, - 114, - 524, - 126 - ], - "spans": [ - { - "bbox": [ - 70, - 114, - 524, - 126 - ], - "type": "text", - "content": "all’80%, il DPP 26 si può ottenere più semplicemente partendo dal 4-bromobenzonitrile", - "score": 1.0, - "cross_page": true - } - ] - }, - { - "bbox": [ - 69, - 134, - 379, - 146 - ], - "spans": [ - { - "bbox": [ - 69, - 134, - 379, - 146 - ], - "type": "text", - "content": "utilizzando il metodo di Iqbal riportato nella sezione precedente.", - "score": 1.0, - "cross_page": true - } - ] - } - ], - "merge_prev": false - } - ] - }, - { - "preproc_blocks": [ - { - "bbox": [ - 66, - 70, - 527, - 148 - ], - "type": "text", - "angle": 0, - "index": 0, - "lines": [ - { - "bbox": [ - 69, - 73, - 524, - 84 - ], - "spans": [ - { - "bbox": [ - 69, - 73, - 524, - 84 - ], - "type": "text", - "content": "cloro si ottiene il prodotto in cui quest’ultimo viene addizionato ai doppi legami dell’unità", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 92, - 524, - 105 - ], - "spans": [ - { - "bbox": [ - 69, - 92, - 524, - 105 - ], - "type": "text", - "content": "centrale di DPP (28). Sebbene la bromurazione del DPP 3 abbia una buona resa, superiore", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 114, - 524, - 126 - ], - "spans": [ - { - "bbox": [ - 70, - 114, - 524, - 126 - ], - "type": "text", - "content": "all’80%, il DPP 26 si può ottenere più semplicemente partendo dal 4-bromobenzonitrile", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 134, - 379, - 146 - ], - "spans": [ - { - "bbox": [ - 69, - 134, - 379, - 146 - ], - "type": "text", - "content": "utilizzando il metodo di Iqbal riportato nella sezione precedente.", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - }, - { - "type": "image", - "bbox": [ - 148, - 165, - 443, - 377 - ], - "blocks": [ - { - "bbox": [ - 148, - 165, - 443, - 377 - ], - "type": "image_body", - "angle": 0, - "lines": [ - { - "bbox": [ - 148, - 165, - 443, - 377 - ], - "spans": [ - { - "bbox": [ - 148, - 165, - 443, - 377 - ], - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/2450b4ec-54d1-41b5-85f2-f45c8f45084f/a6d0c2b1e32b84cb966e857c4cb74e90468ba7853ea4180a685a1f3226e2caad.jpg" - } - ] - } - ], - "index": 1 - }, - { - "bbox": [ - 149, - 386, - 445, - 400 - ], - "type": "image_caption", - "angle": 0, - "index": 2, - "lines": [ - { - "bbox": [ - 152, - 389, - 442, - 398 - ], - "spans": [ - { - "bbox": [ - 152, - 389, - 442, - 398 - ], - "type": "text", - "content": "Figura 20 - reazioni di sostituzione elettrofile aromatiche sugli anelli del DPP 3", - "score": 1.0 - } - ] - } - ] - } - ], - "index": 1 - }, - { - "bbox": [ - 66, - 410, - 527, - 510 - ], - "type": "text", - "angle": 0, - "index": 3, - "lines": [ - { - "bbox": [ - 70, - 412, - 523, - 423 - ], - "spans": [ - { - "bbox": [ - 70, - 412, - 523, - 423 - ], - "type": "text", - "content": "Una delle reazioni più utili per le successive funzionalizzazioni è la bromurazione dei DPP N-", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 431, - 523, - 445 - ], - "spans": [ - { - "bbox": [ - 69, - 433, - 238, - 445 - ], - "type": "text", - "content": "N’-disostituiti che, nelle posizioni", - "score": 1.0 - }, - { - "bbox": [ - 238, - 431, - 268, - 445 - ], - "type": "inline_equation", - "content": "3 \\mathrm { ~ e ~ } 6 ,", - "score": 0.5849 - }, - { - "bbox": [ - 268, - 433, - 523, - 445 - ], - "type": "text", - "content": "possiedono sostituenti eteroaromatici come tiofene,", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 452, - 524, - 465 - ], - "spans": [ - { - "bbox": [ - 69, - 452, - 524, - 465 - ], - "type": "text", - "content": "furano o selenofene (Figura 21). A causa della loro alta densità elettronica, questi eterocicli", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 474, - 524, - 486 - ], - "spans": [ - { - "bbox": [ - 69, - 474, - 524, - 486 - ], - "type": "text", - "content": "reagiscono facilmente con NBS per dare i corrispondenti derivati bromurati con buone rese. La", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 492, - 499, - 507 - ], - "spans": [ - { - "bbox": [ - 69, - 495, - 179, - 506 - ], - "type": "text", - "content": "bromurazione del DPP", - "score": 1.0 - }, - { - "bbox": [ - 181, - 492, - 219, - 507 - ], - "type": "inline_equation", - "content": "2 9 \\mathrm { ~ e ~ } 3 0", - "score": 0.4543 - }, - { - "bbox": [ - 220, - 496, - 499, - 506 - ], - "type": "text", - "content": "può essere effettuata anche utilizzando bromo elementare.", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - }, - { - "type": "image", - "bbox": [ - 131, - 526, - 462, - 660 - ], - "blocks": [ - { - "bbox": [ - 131, - 526, - 462, - 660 - ], - "type": "image_body", - "angle": 0, - "lines": [ - { - "bbox": [ - 131, - 526, - 462, - 660 - ], - "spans": [ - { - "bbox": [ - 131, - 526, - 462, - 660 - ], - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/2450b4ec-54d1-41b5-85f2-f45c8f45084f/b933e7c220a76882cc561e62bcab44a9ed60335dcafa353618f0a3a8eb36ade4.jpg" - } - ] - } - ], - "index": 4 - }, - { - "bbox": [ - 142, - 666, - 451, - 679 - ], - "type": "image_caption", - "angle": 0, - "index": 5, - "lines": [ - { - "bbox": [ - 145, - 668, - 449, - 677 - ], - "spans": [ - { - "bbox": [ - 145, - 668, - 449, - 677 - ], - "type": "text", - "content": "Figura 21 - bromurazione del DPP con sostituenti eteroaromatici in posizione 3 e 6", - "score": 1.0 - } - ] - } - ] - } - ], - "index": 4 - }, - { - "bbox": [ - 67, - 698, - 526, - 735 - ], - "type": "text", - "angle": 0, - "index": 6, - "lines": [ - { - "bbox": [ - 69, - 699, - 524, - 711 - ], - "spans": [ - { - "bbox": [ - 69, - 699, - 524, - 711 - ], - "type": "text", - "content": "La sintesi dei DPP 32, 33 e 34 è difficile da realizzare mediante il metodo che sfrutta gli esteri", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 719, - 524, - 733 - ], - "spans": [ - { - "bbox": [ - 69, - 719, - 524, - 733 - ], - "type": "text", - "content": "succinici combinati con i corrispondenti nitrili: questo è dovuto al fatto che, in condizioni", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - } - ], - "discarded_blocks": [ - { - "bbox": [ - 511, - 785, - 525, - 798 - ], - "type": "page_number", - "angle": 0, - "index": 7, - "lines": [ - { - "bbox": [ - 510, - 786, - 525, - 798 - ], - "spans": [ - { - "bbox": [ - 510, - 786, - 525, - 798 - ], - "type": "text", - "content": "16", - "score": 1.0 - } - ] - } - ] - } - ], - "page_size": [ - 595, - 841 - ], - "page_idx": 21, - "para_blocks": [ - { - "bbox": [ - 66, - 70, - 527, - 148 - ], - "type": "text", - "angle": 0, - "index": 0, - "lines": [], - "merge_prev": false, - "lines_deleted": true - }, - { - "type": "image", - "bbox": [ - 148, - 165, - 443, - 377 - ], - "blocks": [ - { - "bbox": [ - 148, - 165, - 443, - 377 - ], - "type": "image_body", - "angle": 0, - "lines": [ - { - "bbox": [ - 148, - 165, - 443, - 377 - ], - "spans": [ - { - "bbox": [ - 148, - 165, - 443, - 377 - ], - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/2450b4ec-54d1-41b5-85f2-f45c8f45084f/a6d0c2b1e32b84cb966e857c4cb74e90468ba7853ea4180a685a1f3226e2caad.jpg" - } - ] - } - ], - "index": 1 - }, - { - "bbox": [ - 149, - 386, - 445, - 400 - ], - "type": "image_caption", - "angle": 0, - "index": 2, - "lines": [ - { - "bbox": [ - 152, - 389, - 442, - 398 - ], - "spans": [ - { - "bbox": [ - 152, - 389, - 442, - 398 - ], - "type": "text", - "content": "Figura 20 - reazioni di sostituzione elettrofile aromatiche sugli anelli del DPP 3", - "score": 1.0 - } - ] - } - ] - } - ], - "index": 1 - }, - { - "bbox": [ - 66, - 410, - 527, - 510 - ], - "type": "text", - "angle": 0, - "index": 3, - "lines": [ - { - "bbox": [ - 70, - 412, - 523, - 423 - ], - "spans": [ - { - "bbox": [ - 70, - 412, - 523, - 423 - ], - "type": "text", - "content": "Una delle reazioni più utili per le successive funzionalizzazioni è la bromurazione dei DPP N-", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 431, - 523, - 445 - ], - "spans": [ - { - "bbox": [ - 69, - 433, - 238, - 445 - ], - "type": "text", - "content": "N’-disostituiti che, nelle posizioni", - "score": 1.0 - }, - { - "bbox": [ - 238, - 431, - 268, - 445 - ], - "type": "inline_equation", - "content": "3 \\mathrm { ~ e ~ } 6 ,", - "score": 0.5849 - }, - { - "bbox": [ - 268, - 433, - 523, - 445 - ], - "type": "text", - "content": "possiedono sostituenti eteroaromatici come tiofene,", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 452, - 524, - 465 - ], - "spans": [ - { - "bbox": [ - 69, - 452, - 524, - 465 - ], - "type": "text", - "content": "furano o selenofene (Figura 21). A causa della loro alta densità elettronica, questi eterocicli", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 474, - 524, - 486 - ], - "spans": [ - { - "bbox": [ - 69, - 474, - 524, - 486 - ], - "type": "text", - "content": "reagiscono facilmente con NBS per dare i corrispondenti derivati bromurati con buone rese. 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200, - 505, - 216 - ], - "type": "image_caption", - "angle": 0, - "index": 2, - "lines": [ - { - "bbox": [ - 70, - 201, - 504, - 214 - ], - "spans": [ - { - "bbox": [ - 70, - 201, - 504, - 214 - ], - "type": "text", - "content": "Sono stati sintetizzati tre copolimeri in base alla percentuale di DPP utilizzata (Tabella 3).", - "score": 1.0 - } - ] - } - ] - } - ], - "index": 1 - }, - { - "type": "table", - "bbox": [ - 69, - 235, - 524, - 321 - ], - "blocks": [ - { - "bbox": [ - 223, - 221, - 372, - 232 - ], - "type": "table_caption", - "angle": 0, - "index": 3, - "lines": [ - { - "bbox": [ - 224, - 222, - 370, - 232 - ], - "spans": [ - { - "bbox": [ - 224, - 222, - 370, - 232 - ], - "type": "text", - "content": "Tabella 3 - composizione dei copolimeri", - "score": 1.0 - } - ] - } - ] - }, - { - "bbox": [ - 69, - 235, - 524, - 321 - ], - "type": "table_body", - "angle": 0, - "lines": [ - { - "bbox": [ - 69, - 235, - 524, - 321 - ], - "spans": [ - { - "bbox": [ - 69, - 235, - 524, - 321 - 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CopolimeroDPP (mmol)DPP (eq)3HT (mmol)3HT (eq)
3a0.20.20.80.8
3b0.50.50.50.5
3c0.80.80.20.2
", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/2450b4ec-54d1-41b5-85f2-f45c8f45084f/bdab0a9fb6418bb2cfa88117b9fcf9c5ba879eed3568327895694371a3968cde.jpg" - } - ] - } - ], - "index": 4 - } - ], - "index": 4 - }, - { - "bbox": [ - 67, - 334, - 526, - 495 - ], - "type": "text", - "angle": 0, - "index": 5, - "lines": [ - { - "bbox": [ - 69, - 335, - 524, - 348 - ], - "spans": [ - { - "bbox": [ - 69, - 335, - 524, - 348 - ], - "type": "text", - "content": "La procedura sperimentale risulta analoga per ognuno dei copolimeri sintetizzati. In un pallone", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 357, - 524, - 368 - ], - "spans": [ - { - "bbox": [ - 69, - 357, - 524, - 368 - ], - "type": "text", - "content": "a tre colli posto in atmosfera d’azoto, vengono aggiunti 40 mL di cloroformio anidro (CHCl3)", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 377, - 524, - 389 - ], - "spans": [ - { - "bbox": [ - 70, - 377, - 524, - 389 - ], - "type": "text", - "content": "ed i due monomeri nelle proporzioni corrette. La completa solubilizzazione del prodotto 2 viene", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 396, - 524, - 410 - ], - "spans": [ - { - "bbox": [ - 69, - 396, - 524, - 410 - ], - "type": "text", - "content": "favorita mediante sonicatore. In parallelo, si prepara una soluzione di 818 mg di tricloruro", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 417, - 524, - 431 - ], - "spans": [ - { - "bbox": [ - 69, - 418, - 351, - 430 - ], - "type": "text", - "content": "ferrico (FeCl3) (5.05 mmol, 5 eq) in 10 mL di nitrometano", - "score": 1.0 - }, - { - "bbox": [ - 353, - 417, - 404, - 431 - ], - "type": "inline_equation", - "content": "\\mathrm { ( C H } _ { 3 } \\mathrm { N O } _ { 2 } \\mathrm { ) }", - "score": 0.8382 - }, - { - "bbox": [ - 404, - 419, - 524, - 429 - ], - "type": "text", - "content": ", lasciandola anch'essa in", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 439, - 524, - 451 - ], - "spans": [ - { - "bbox": [ - 69, - 439, - 524, - 451 - ], - "type": "text", - "content": "sonicatore per alcuni minuti per agevolarne la dissoluzione. La soluzione ossidante viene", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 460, - 524, - 471 - ], - "spans": [ - { - "bbox": [ - 70, - 460, - 524, - 471 - ], - "type": "text", - "content": "sgocciolata nel pallone mantenendo il sistema in agitazione per 1 h. Al termine, si aggiungono", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 481, - 421, - 492 - ], - "spans": [ - { - "bbox": [ - 69, - 481, - 421, - 492 - ], - "type": "text", - "content": "30 mL di THF sbiancato e si lascia nuovamente in agitazione per 30 min.", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - }, - { - "bbox": [ - 67, - 500, - 527, - 682 - ], - "type": "text", - "angle": 0, - "index": 6, - "lines": [ - { - "bbox": [ - 70, - 501, - 524, - 513 - ], - "spans": [ - { - "bbox": [ - 70, - 501, - 524, - 513 - ], - "type": "text", - "content": "Successivamente, si trasferisce il grezzo di reazione in imbuto separatore e si lava con HCl 0.6", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 521, - 523, - 533 - ], - "spans": [ - { - "bbox": [ - 69, - 521, - 523, - 533 - ], - "type": "text", - "content": "M finché la fase acquosa sottoposta al saggio con tiocianato non risulta trasparente (la", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 542, - 524, - 555 - ], - "spans": [ - { - "bbox": [ - 69, - 542, - 524, - 555 - ], - "type": "text", - "content": "persistenza del colore rosso indica la presenza di tracce residue di tricloruro ferrico; il test si", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 562, - 525, - 575 - ], - "spans": [ - { - "bbox": [ - 69, - 562, - 525, - 575 - ], - "type": "text", - "content": "esegue a partire dal terzo lavaggio). La fase organica viene estratta con una soluzione satura di", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 584, - 524, - 596 - ], - "spans": [ - { - "bbox": [ - 69, - 584, - 524, - 596 - ], - "type": "text", - "content": "NaCl in acqua, anidrificata e evaporata mediante rotavapor. Per separare il polimero dai", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 604, - 524, - 617 - ], - "spans": [ - { - "bbox": [ - 69, - 604, - 524, - 617 - ], - "type": "text", - "content": "possibili sottoprodotti (poli-3esiltiofene) e dalle molecole a basso peso molecolare viene", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 624, - 524, - 637 - ], - "spans": [ - { - "bbox": [ - 70, - 624, - 524, - 637 - ], - "type": "text", - "content": "effettuata una precipitazione in non-solvente. Il prodotto viene solubilizzato nella minima", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 646, - 524, - 659 - ], - "spans": [ - { - "bbox": [ - 70, - 646, - 524, - 659 - ], - "type": "text", - "content": "quantità di THF e si fa gocciolare in 150 mL di metanolo freddo. 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CopolimeroDPP (mmol)DPP (eq)3HT (mmol)3HT (eq)
3a0.20.20.80.8
3b0.50.50.50.5
3c0.80.80.20.2
", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/2450b4ec-54d1-41b5-85f2-f45c8f45084f/bdab0a9fb6418bb2cfa88117b9fcf9c5ba879eed3568327895694371a3968cde.jpg" - } - ] - } - ], - "index": 4 - } - ], - "index": 4 - }, - { - "bbox": [ - 67, - 334, - 526, - 495 - ], - "type": "text", - "angle": 0, - "index": 5, - "lines": [ - { - "bbox": [ - 69, - 335, - 524, - 348 - ], - "spans": [ - { - "bbox": [ - 69, - 335, - 524, - 348 - ], - "type": "text", - "content": "La procedura sperimentale risulta analoga per ognuno dei copolimeri sintetizzati. In un pallone", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 357, - 524, - 368 - ], - "spans": [ - { - "bbox": [ - 69, - 357, - 524, - 368 - ], - "type": "text", - "content": "a tre colli posto in atmosfera d’azoto, vengono aggiunti 40 mL di cloroformio anidro (CHCl3)", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 377, - 524, - 389 - ], - "spans": [ - { - "bbox": [ - 70, - 377, - 524, - 389 - ], - "type": "text", - "content": "ed i due monomeri nelle proporzioni corrette. La completa solubilizzazione del prodotto 2 viene", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 396, - 524, - 410 - ], - "spans": [ - { - "bbox": [ - 69, - 396, - 524, - 410 - ], - "type": "text", - "content": "favorita mediante sonicatore. In parallelo, si prepara una soluzione di 818 mg di tricloruro", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 417, - 524, - 431 - ], - "spans": [ - { - "bbox": [ - 69, - 418, - 351, - 430 - ], - "type": "text", - "content": "ferrico (FeCl3) (5.05 mmol, 5 eq) in 10 mL di nitrometano", - "score": 1.0 - }, - { - "bbox": [ - 353, - 417, - 404, - 431 - ], - "type": "inline_equation", - "content": "\\mathrm { ( C H } _ { 3 } \\mathrm { N O } _ { 2 } \\mathrm { ) }", - "score": 0.8382 - }, - { - "bbox": [ - 404, - 419, - 524, - 429 - ], - "type": "text", - "content": ", lasciandola anch'essa in", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 439, - 524, - 451 - ], - "spans": [ - { - "bbox": [ - 69, - 439, - 524, - 451 - ], - "type": "text", - "content": "sonicatore per alcuni minuti per agevolarne la dissoluzione. La soluzione ossidante viene", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 460, - 524, - 471 - ], - "spans": [ - { - "bbox": [ - 70, - 460, - 524, - 471 - ], - "type": "text", - "content": "sgocciolata nel pallone mantenendo il sistema in agitazione per 1 h. Al termine, si aggiungono", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 481, - 421, - 492 - ], - "spans": [ - { - "bbox": [ - 69, - 481, - 421, - 492 - ], - "type": "text", - "content": "30 mL di THF sbiancato e si lascia nuovamente in agitazione per 30 min.", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - }, - { - "bbox": [ - 67, - 500, - 527, - 682 - ], - "type": "text", - "angle": 0, - "index": 6, - "lines": [ - { - "bbox": [ - 70, - 501, - 524, - 513 - ], - "spans": [ - { - "bbox": [ - 70, - 501, - 524, - 513 - ], - "type": "text", - "content": "Successivamente, si trasferisce il grezzo di reazione in imbuto separatore e si lava con HCl 0.6", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 521, - 523, - 533 - ], - "spans": [ - { - "bbox": [ - 69, - 521, - 523, - 533 - ], - "type": "text", - "content": "M finché la fase acquosa sottoposta al saggio con tiocianato non risulta trasparente (la", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 542, - 524, - 555 - ], - "spans": [ - { - "bbox": [ - 69, - 542, - 524, - 555 - ], - "type": "text", - "content": "persistenza del colore rosso indica la presenza di tracce residue di tricloruro ferrico; il test si", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 562, - 525, - 575 - ], - "spans": [ - { - "bbox": [ - 69, - 562, - 525, - 575 - ], - "type": "text", - "content": "esegue a partire dal terzo lavaggio). La fase organica viene estratta con una soluzione satura di", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 584, - 524, - 596 - ], - "spans": [ - { - "bbox": [ - 69, - 584, - 524, - 596 - ], - "type": "text", - "content": "NaCl in acqua, anidrificata e evaporata mediante rotavapor. Per separare il polimero dai", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 604, - 524, - 617 - ], - "spans": [ - { - "bbox": [ - 69, - 604, - 524, - 617 - ], - "type": "text", - "content": "possibili sottoprodotti (poli-3esiltiofene) e dalle molecole a basso peso molecolare viene", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 624, - 524, - 637 - ], - "spans": [ - { - "bbox": [ - 70, - 624, - 524, - 637 - ], - "type": "text", - "content": "effettuata una precipitazione in non-solvente. 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CopolimeroMn teoricoCaprolattone
V (ml)mol
3b1500 Da (3.1b)1.060.01
5000 Da (3.2b)4.650.04
10000 Da (3.3b)9.290.09
3c1500 Da (3.1c)1.720.02
5000 Da (3.2c)7.430.07
10000 Da (3.3c)14.870.1
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Il sistema è stato riscaldato mediante bagno", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 565, - 524, - 577 - ], - "spans": [ - { - "bbox": [ - 70, - 565, - 524, - 577 - ], - "type": "text", - "content": "ad olio siliconico ed il solvente è stato rimosso a pressione ridotta utilizzando una pompa a", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 586, - 524, - 597 - ], - "spans": [ - { - "bbox": [ - 69, - 586, - 524, - 597 - ], - "type": "text", - "content": "membrana. Ottenuto un residuo secco, il pallone è stato posto in atmosfera inerte di azoto. Sono", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 607, - 524, - 618 - ], - "spans": [ - { - "bbox": [ - 70, - 607, - 524, - 618 - ], - "type": "text", - "content": "stati quindi aggiunti 2 mL di toluene e la quantità di caprolattone indicata in Tabella 4. La", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 625, - 524, - 640 - ], - "spans": [ - { - "bbox": [ - 69, - 628, - 295, - 640 - ], - "type": "text", - "content": "soluzione è stata portata alla temperatura di", - "score": 1.0 - }, - { - "bbox": [ - 298, - 625, - 336, - 640 - ], - "type": "inline_equation", - "content": "1 1 0 ~ ^ { \\circ } \\mathrm { C } .", - "score": 0.6482 - }, - { - "bbox": [ - 337, - 628, - 524, - 640 - ], - "type": "text", - "content": ", e successivamente, è stato aggiunto", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 647, - 524, - 660 - ], - "spans": [ - { - "bbox": [ - 69, - 647, - 524, - 660 - ], - "type": "text", - "content": "Sn(Oct)2 in quantità catalitica. La miscela di reazione è stata mantenuta a reflusso per 24 h. Il", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 669, - 523, - 681 - ], - "spans": [ - { - "bbox": [ - 69, - 669, - 523, - 681 - ], - "type": "text", - "content": "prodotto è stato purificato mediante precipitazione in non-solvente usando metanolo freddo.", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 689, - 524, - 700 - ], - "spans": [ - { - "bbox": [ - 69, - 689, - 524, - 700 - ], - "type": "text", - "content": "Infine, il polimero precipitato è stato recuperato tramite filtrazione su imbuto Büchner ed", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 710, - 524, - 723 - ], - "spans": [ - { - "bbox": [ - 69, - 710, - 524, - 723 - ], - "type": "text", - "content": "essiccato all'aria sotto cappa aspirante in modo da allontanare ogni eventuale traccia di solvente", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 67, - 729, - 110, - 742 - ], - "spans": [ - { - "bbox": [ - 67, - 729, - 110, - 742 - ], - "type": "text", - "content": "residuo.", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - } - ], - "discarded_blocks": [ - { - "bbox": [ - 511, - 785, - 525, - 797 - ], - "type": "page_number", - "angle": 0, - "index": 6, - "lines": [ - { - "bbox": [ - 509, - 786, - 525, - 798 - ], - "spans": [ - { - "bbox": [ - 509, - 786, - 525, - 798 - ], - "type": "text", - "content": "42", - "score": 1.0 - } - ] - } - ] - } - ], - "page_size": [ - 595, - 841 - ], - "page_idx": 47, - "para_blocks": [ - { - "bbox": [ - 68, - 71, - 229, - 85 - ], - "type": "title", - "angle": 0, - "index": 0, - "lines": [ - { - "bbox": [ - 70, - 72, - 227, - 84 - ], - "spans": [ - { - "bbox": [ - 70, - 72, - 227, - 84 - ], - "type": "text", - "content": "Sintesi dei polimeri bottle brush", - "score": 1.0 - } - ] - } - ], - "level": 2 - }, - { - "type": "image", - "bbox": [ - 70, - 104, - 522, - 186 - ], - "blocks": [ - { - "bbox": [ - 70, - 104, - 522, - 186 - ], - "type": "image_body", - "angle": 0, - "lines": [ - { - "bbox": [ - 70, - 104, - 522, - 186 - ], - "spans": [ - { - "bbox": [ - 70, - 104, - 522, - 186 - ], - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/2450b4ec-54d1-41b5-85f2-f45c8f45084f/136800375cf0b441570672093e255d90a47c45a009bd254929fb74b1f17b382d.jpg" - } - ] - } - ], - "index": 1 - } - ], - "index": 1 - }, - { - "bbox": [ - 67, - 206, - 526, - 285 - ], - "type": "text", - "angle": 0, - "index": 2, - "lines": [ - { - "bbox": [ - 69, - 208, - 525, - 220 - ], - "spans": [ - { - "bbox": [ - 69, - 208, - 525, - 220 - ], - "type": "text", - "content": "A partire dai campioni 3b e 3c sono stati realizzati copolimeri con struttura bottle-brush a", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 229, - 525, - 241 - ], - "spans": [ - { - "bbox": [ - 69, - 229, - 525, - 241 - ], - "type": "text", - "content": "diverso peso molecolare. 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CopolimeroMn teoricoCaprolattone
V (ml)mol
3b1500 Da (3.1b)1.060.01
5000 Da (3.2b)4.650.04
10000 Da (3.3b)9.290.09
3c1500 Da (3.1c)1.720.02
5000 Da (3.2c)7.430.07
10000 Da (3.3c)14.870.1
", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/2450b4ec-54d1-41b5-85f2-f45c8f45084f/712add6c345484326022d45f29fa41a2aa219c4df9ef664e336e3025855726e8.jpg" - } - ] - } - ], - "index": 4 - } - ], - "index": 4 - }, - { - "bbox": [ - 67, - 502, - 527, - 745 - ], - "type": "text", - "angle": 0, - "index": 5, - "lines": [ - { - "bbox": [ - 69, - 503, - 524, - 515 - ], - "spans": [ - { - "bbox": [ - 69, - 503, - 524, - 515 - ], - "type": "text", - "content": "La procedura sintetica adottata è risultata analoga per tutti i polimeri descritti in Tabella 4.", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 523, - 524, - 535 - ], - "spans": [ - { - "bbox": [ - 70, - 523, - 524, - 535 - ], - "type": "text", - "content": "All'interno di un pallone da 30 mL dotato di rubinetto è stato introdotto il copolimero (nei", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 544, - 524, - 557 - ], - "spans": [ - { - "bbox": [ - 70, - 544, - 524, - 557 - ], - "type": "text", - "content": "quantitativi indicati in Tabella 4) sciolto in THF. 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Il compito del controelettrodo è", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 412, - 524, - 423 - ], - "spans": [ - { - "bbox": [ - 69, - 412, - 524, - 423 - ], - "type": "text", - "content": "quello di permettere il passaggio della corrente necessaria a bilanciare la reazione faradica che", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 433, - 236, - 445 - ], - "spans": [ - { - "bbox": [ - 70, - 433, - 236, - 445 - ], - "type": "text", - "content": "si sviluppa sull'elettrodo di lavoro.", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - }, - { - "bbox": [ - 66, - 452, - 527, - 738 - ], - "type": "text", - "angle": 0, - "index": 3, - "lines": [ - { - "bbox": [ - 69, - 454, - 524, - 465 - ], - "spans": [ - { - "bbox": [ - 69, - 454, - 524, - 465 - ], - "type": "text", - "content": "Il principio fondamentale della tecnica consiste nell'imporre all'elettrodo di lavoro un potenziale", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 475, - 523, - 486 - ], - "spans": [ - { - "bbox": [ - 69, - 475, - 523, - 486 - ], - "type": "text", - "content": "che varia linearmente nel tempo secondo un'onda triangolare. 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La formazione di tale picco si verifica poiché lo strato di soluzione immediatamente", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 218, - 524, - 230 - ], - "spans": [ - { - "bbox": [ - 69, - 218, - 524, - 230 - ], - "type": "text", - "content": "adiacente all'elettrodo si impoverisce rapidamente della specie reagente, rendendo il processo", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 238, - 524, - 251 - ], - "spans": [ - { - "bbox": [ - 69, - 238, - 524, - 251 - ], - "type": "text", - "content": "limitato dalla velocità di diffusione del materiale dal bulk della soluzione. Subito dopo il", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 260, - 524, - 272 - ], - "spans": [ - { - "bbox": [ - 69, - 260, - 524, - 272 - ], - "type": "text", - "content": "superamento del picco, lo strato di diffusione si espande verso l'interno della soluzione", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 280, - 524, - 293 - ], - "spans": [ - { - "bbox": [ - 69, - 280, - 524, - 293 - ], - "type": "text", - "content": "attenuando il gradiente di concentrazione, e conseguentemente la corrente decresce", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 299, - 525, - 314 - ], - "spans": [ - { - "bbox": [ - 69, - 302, - 175, - 314 - ], - "type": "text", - "content": "proporzionalmente a", - "score": 1.0 - }, - { - "bbox": [ - 176, - 299, - 195, - 313 - ], - "type": "inline_equation", - "content": "\\mathrm { t } ^ { - 1 / 2 }", - "score": 0.5897 - }, - { - "bbox": [ - 195, - 302, - 525, - 314 - ], - "type": "text", - "content": ", seguendo l'equazione di Cottrell (Equazione 7) dove �(�) è la", - 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"score": 0.595 - }, - { - "bbox": [ - 93, - 364, - 469, - 377 - ], - "type": "text", - "content": "la concentrazione della specie reagente nel bulk della soluzione e � è il tempo.", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - }, - { - "bbox": [ - 247, - 396, - 346, - 428 - ], - "type": "interline_equation", - "angle": 0, - "lines": [ - { - "bbox": [ - 247, - 396, - 346, - 428 - ], - "spans": [ - { - "bbox": [ - 247, - 396, - 346, - 428 - ], - "type": "interline_equation", - "content": "I (t) = \\frac {n F A D ^ {1 / 2} C ^ {*}}{\\pi^ {1 / 2} t ^ {1 / 2}}", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/2450b4ec-54d1-41b5-85f2-f45c8f45084f/dec2be3c0dcdc29da5fb3e031ad282d1de9208ee241f5b35ead53f6a5b558a0e.jpg" - } - ] - } - ], - "index": 4 - }, - { - "bbox": [ - 230, - 436, - 364, - 449 - ], - "type": "text", - "angle": 0, - "index": 5, - "lines": [ - { - "bbox": [ - 233, - 439, - 361, - 448 - ], - "spans": [ - { - "bbox": [ - 233, - 439, - 361, - 448 - 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186, - 583, - 406, - 600 - ], - "type": "interline_equation", - "content": "I _ {p} = (2. 6 9 \\times 1 0 ^ {5}) \\cdot n ^ {3 / 2} \\cdot A \\cdot D ^ {1 / 2} \\cdot C \\cdot v ^ {1 / 2}", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/2450b4ec-54d1-41b5-85f2-f45c8f45084f/46f970280fb1d95468a231478412d650ef993f70477cea26b3d3b0d067ccfa97.jpg" - } - ] - } - ], - "index": 8 - }, - { - "bbox": [ - 216, - 607, - 377, - 619 - ], - "type": "interline_equation", - "angle": 0, - "lines": [ - { - "bbox": [ - 216, - 607, - 377, - 619 - ], - "spans": [ - { - "bbox": [ - 216, - 607, - 377, - 619 - ], - "type": "interline_equation", - "content": "E q u a z i o n e 8 - e q u a z i o n e d i R a n d l e s - S e v c i k", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/2450b4ec-54d1-41b5-85f2-f45c8f45084f/7ac3d95eab44bfce7ca7ce350ce18f11e29e7a06cb1e37a88c2056a1cf141437.jpg" - } - ] - } - ], - "index": 9 - }, - { - "bbox": [ - 66, - 629, - 527, - 753 - ], - "type": "text", - 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Procedure sperimentali delle analisi voltammetriche", - "score": 1.0 - } - ] - } - ], - "level": 2 - }, - { - "bbox": [ - 66, - 101, - 526, - 199 - ], - "type": "text", - "angle": 0, - "index": 1, - "lines": [ - { - "bbox": [ - 69, - 102, - 523, - 114 - ], - "spans": [ - { - "bbox": [ - 69, - 102, - 523, - 114 - ], - "type": "text", - "content": "Le caratterizzazioni elettrochimiche sono state condotte a temperatura ambiente impiegando un", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 122, - 524, - 134 - ], - "spans": [ - { - "bbox": [ - 69, - 122, - 524, - 134 - ], - "type": "text", - "content": "potenziostato CHI660C (CH Instruments), interfacciato con una cella elettrochimica standard", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 143, - 524, - 156 - ], - "spans": [ - { - "bbox": [ - 69, - 143, - 524, - 156 - ], - "type": "text", - "content": "a tre elettrodi. 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A circa 3400", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 425, - 524, - 439 - ], - "spans": [ - { - "bbox": [ - 69, - 425, - 94, - 439 - ], - "type": "inline_equation", - "content": "\\mathrm { c m } ^ { - 1 }", - "score": 0.6163 - }, - { - "bbox": [ - 95, - 426, - 524, - 439 - ], - "type": "text", - "content": "si osserva una banda larga attribuibile allo stretching del legame O-H dei gruppi alcolici", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 445, - 524, - 459 - ], - "spans": [ - { - "bbox": [ - 69, - 446, - 240, - 459 - ], - "type": "text", - "content": "terminali. I segnali deboli intorno a", - "score": 1.0 - }, - { - "bbox": [ - 240, - 445, - 291, - 459 - ], - "type": "inline_equation", - "content": "3 1 0 0 \\mathrm { c m } ^ { - 1 }", - "score": 0.6068 - }, - { - "bbox": [ - 293, - 446, - 524, - 459 - ], - "type": "text", - "content": "corrispondono allo stretching dei C-H aromatici", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 465, - 524, - 481 - ], - "spans": [ - { - "bbox": [ - 70, - 468, - 302, - 478 - ], - "type": "text", - "content": "degli anelli tiofenici, mentre i due picchi netti a", - "score": 1.0 - }, - { - "bbox": [ - 302, - 465, - 392, - 481 - ], - "type": "inline_equation", - "content": "2 9 3 0 \\textup { e } 2 8 5 0 \\textup { c m } ^ { - 1 }", - "score": 0.6021 - }, - { - "bbox": [ - 393, - 467, - 524, - 480 - ], - "type": "text", - "content": "sono tipici dello stretching", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 488, - 525, - 500 - ], - "spans": [ - { - "bbox": [ - 69, - 488, - 525, - 500 - ], - "type": "text", - "content": "(asimmetrico e simmetrico) dei C-H alifatici dei gruppi metilenici. 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Infine, nella zona del", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 571, - 524, - 583 - ], - "spans": [ - { - "bbox": [ - 70, - 571, - 524, - 583 - ], - "type": "text", - "content": "fingerprint, sono presenti dei picchi compatibili lo stretching C-O degli alcol primari e ai", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 592, - 195, - 602 - ], - "spans": [ - { - "bbox": [ - 70, - 592, - 195, - 602 - ], - "type": "text", - "content": "bending dei C-H tiofenici.", - "score": 1.0 - } - ] - } - ] - }, - { - "bbox": [ - 67, - 610, - 526, - 668 - ], - "type": "chart_caption", - "angle": 0, - "index": 3, - "lines": [ - { - "bbox": [ - 69, - 613, - 524, - 624 - ], - "spans": [ - { - "bbox": [ - 69, - 613, - 524, - 624 - ], - "type": "text", - "content": "Per completare la caratterizzazione, il fluoroforo è stato analizzato mediante spettroscopia di", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 633, - 523, - 645 - ], - "spans": [ - { - "bbox": [ - 69, - 633, - 523, - 645 - ], - "type": "text", - "content": "assorbimento (UV-Visibile) e di emissione, in modo da poter confrontare le proprietà foto-", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 654, - 316, - 666 - ], - "spans": [ - { - "bbox": [ - 70, - 654, - 316, - 666 - ], - "type": "text", - "content": "fisiche con quelle del DPP di partenza (Figura 50).", - "score": 1.0 - } - ] - } - ] - } - ], - "index": 1 - } - ], - "discarded_blocks": [ - { - "bbox": [ - 513, - 72, - 525, - 84 - ], - "type": "page_number", - "angle": 0, - "index": 0, - "lines": [ - { - "bbox": [ - 513, - 71, - 525, - 84 - ], - "spans": [ - { - "bbox": [ - 513, - 71, - 525, - 84 - ], - "type": "text", - "content": "in", - "score": 1.0 - } - ] - } - ] - }, - { - "bbox": [ - 511, - 785, - 525, - 798 - ], - "type": "page_number", - "angle": 0, - "index": 4, - "lines": [ - { - "bbox": [ - 509, - 786, - 525, - 799 - ], - "spans": [ - { - "bbox": [ - 509, - 786, - 525, - 799 - ], - "type": "text", - "content": "55", - "score": 1.0 - } - ] - } - ] - } - ], - "page_size": [ - 595, - 841 - ], - "page_idx": 60, - "para_blocks": [ - { - "type": "chart", - "bbox": [ - 70, - 69, - 525, - 398 - ], - "blocks": [ - { - "bbox": [ - 70, - 69, - 525, - 398 - ], - "type": "chart_body", - "angle": 0, - "lines": [ - { - "bbox": [ - 70, - 69, - 525, - 398 - ], - "spans": [ - { - "bbox": [ - 70, - 69, - 525, - 398 - ], - "type": "chart", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/2450b4ec-54d1-41b5-85f2-f45c8f45084f/b2202b1bdc46f9dfa32c389d472cf74b117adeb1b500d2e8c526871dd08ee8ae.jpg" - } - ] - } - ], - "index": 1 - }, - { - "bbox": [ - 67, - 404, - 526, - 606 - ], - "type": "chart_caption", - "angle": 0, - "index": 2, - "lines": [ - { - "bbox": [ - 70, - 405, - 524, - 417 - ], - "spans": [ - { - "bbox": [ - 70, - 405, - 524, - 417 - ], - "type": "text", - "content": "Figura 49 si possono osservare picchi coerenti con la struttura del DPP alchilato. A circa 3400", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 425, - 524, - 439 - ], - "spans": [ - { - "bbox": [ - 69, - 425, - 94, - 439 - ], - "type": "inline_equation", - "content": "\\mathrm { c m } ^ { - 1 }", - "score": 0.6163 - }, - { - "bbox": [ - 95, - 426, - 524, - 439 - ], - "type": "text", - "content": "si osserva una banda larga attribuibile allo stretching del legame O-H dei gruppi alcolici", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 445, - 524, - 459 - ], - "spans": [ - { - "bbox": [ - 69, - 446, - 240, - 459 - ], - "type": "text", - "content": "terminali. 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Allo stato", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 462, - 524, - 476 - ], - "spans": [ - { - "bbox": [ - 69, - 463, - 366, - 475 - ], - "type": "text", - "content": "solido e in solventi non coordinanti come il cloroformio, il", - "score": 1.0 - }, - { - "bbox": [ - 367, - 462, - 396, - 476 - ], - "type": "inline_equation", - "content": "\\mathrm { F e C l } _ { 3 }", - "score": 0.634 - }, - { - "bbox": [ - 398, - 463, - 524, - 474 - ], - "type": "text", - "content": "tende a formare dimeri o", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 484, - 524, - 496 - ], - "spans": [ - { - "bbox": [ - 69, - 484, - 524, - 496 - ], - "type": "text", - "content": "aggregati, nei quali i siti attivi per l'ossidazione sono limitati alla superficie o ai difetti strutturali", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 503, - 523, - 517 - ], - "spans": [ - { - "bbox": [ - 69, - 503, - 523, - 517 - ], - "type": "text", - "content": "dei cluster. L'introduzione del nitrometano nella miscela di reazione risolve questa criticità:", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 526, - 524, - 538 - ], - "spans": [ - { - "bbox": [ - 70, - 526, - 524, - 538 - ], - "type": "text", - "content": "agendo come legante, esso rompe i ponti alogeno intermolecolari, spezzando i dimeri e", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 546, - 525, - 558 - ], - "spans": [ - { - "bbox": [ - 69, - 546, - 525, - 558 - ], - "type": "text", - "content": "solvatando il cloruro ferrico. La formazione di questi complessi di coordinazione con il", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 567, - 524, - 579 - ], - "spans": [ - { - "bbox": [ - 69, - 567, - 524, - 579 - ], - "type": "text", - "content": "nitrometano attiva di fatto il sistema, generando una soluzione omogenea di centri metallici", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 587, - 525, - 599 - ], - "spans": [ - { - "bbox": [ - 70, - 587, - 525, - 599 - ], - "type": "text", - "content": "discreti e stericamente accessibili per il trasferimento elettronico. Parallelamente, la", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 608, - 523, - 619 - ], - "spans": [ - { - "bbox": [ - 70, - 608, - 523, - 619 - ], - "type": "text", - "content": "coordinazione del ferro con il nitrometano ne modera sensibilmente sia la forte acidità di Lewis", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 629, - 524, - 640 - ], - "spans": [ - { - "bbox": [ - 70, - 629, - 524, - 640 - ], - "type": "text", - "content": "che il potenziale ossidante. Questa azione attenuatrice è essenziale per indirizzare la cinetica di", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 650, - 523, - 661 - ], - "spans": [ - { - "bbox": [ - 69, - 650, - 523, - 661 - ], - "type": "text", - "content": "reazione: controllando la forza dell'ossidante, si prevengono reazioni secondarie come l'iper-", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 671, - 524, - 682 - ], - "spans": [ - { - "bbox": [ - 70, - 671, - 524, - 682 - ], - "type": "text", - "content": "ossidazione della catena o l'insorgere di difetti di reticolazione (cross-linking). Di conseguenza", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 691, - 524, - 703 - ], - "spans": [ - { - "bbox": [ - 70, - 691, - 524, - 703 - ], - "type": "text", - "content": "si migliora la regioselettività della polimerizzazione, massimizzando la regolarità strutturale e", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 712, - 451, - 724 - ], - "spans": [ - { - "bbox": [ - 69, - 712, - 451, - 724 - ], - "type": "text", - "content": "l'estensione della π-coniugazione nel copolimero semiconduttore 3 sintetizzato.", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - }, - { - "bbox": [ - 67, - 731, - 526, - 767 - ], - "type": "text", - "angle": 0, - "index": 4, - "lines": [ - { - "bbox": [ - 70, - 733, - 523, - 744 - ], - "spans": [ - { - "bbox": [ - 70, - 733, - 523, - 744 - ], - "type": "text", - "content": "Come solvente di reazione, invece, è stato scelto di utilizzare il cloroformio anidro, necessario", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 752, - 524, - 766 - ], - "spans": [ - { - "bbox": [ - 69, - 752, - 524, - 766 - ], - "type": "text", - "content": "per prevenire reazioni secondarie indotte dall'umidità. L'acqua, agendo come nucleofilo e base", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 72, - 524, - 84 - ], - "spans": [ - { - "bbox": [ - 70, - 72, - 524, - 84 - ], - "type": "text", - "content": "di Lewis, potrebbe interferire con il processo di polimerizzazione attraverso due meccanismi", - "score": 1.0, - "cross_page": true - } - ] - }, - { - "bbox": [ - 69, - 93, - 524, - 104 - ], - "spans": [ - { - "bbox": [ - 69, - 93, - 524, - 104 - ], - "type": "text", - "content": "competitivi. In primo luogo, si potrebbe coordinare al FeCl3 formando specie idrate stabili; ciò", - "score": 1.0, - "cross_page": true - } - ] - }, - { - "bbox": [ - 69, - 114, - 524, - 126 - ], - "spans": [ - { - "bbox": [ - 69, - 114, - 524, - 126 - ], - "type": "text", - "content": "saturerebbe la sfera di coordinazione del metallo, riducendone il potenziale ossidativo e", - "score": 1.0, - "cross_page": true - } - ] - }, - { - "bbox": [ - 70, - 134, - 524, - 146 - ], - "spans": [ - { - "bbox": [ - 70, - 134, - 524, - 146 - ], - "type": "text", - "content": "inibendo l'innesco della reazione. In secondo luogo, l'acqua potrebbe causare il quenching degli", - "score": 1.0, - "cross_page": true - } - ] - }, - { - "bbox": [ - 69, - 155, - 524, - 167 - ], - "spans": [ - { - "bbox": [ - 69, - 155, - 524, - 167 - ], - "type": "text", - "content": "intermedi cationico-radicalici in propagazione. Questo attacco nucleofilo porterebbe alla", - "score": 1.0, - "cross_page": true - } - ] - }, - { - "bbox": [ - 69, - 175, - 523, - 188 - ], - "spans": [ - { - "bbox": [ - 69, - 175, - 523, - 188 - ], - "type": "text", - "content": "terminazione prematura della catena polimerica e all'introduzione di difetti strutturali, i quali", - "score": 1.0, - "cross_page": true - } - ] - }, - { - "bbox": [ - 69, - 196, - 524, - 208 - ], - "spans": [ - { - "bbox": [ - 69, - 196, - 524, - 208 - ], - "type": "text", - "content": "interromperebbero la coniugazione della catena compromettendo le proprietà semiconduttrici", - "score": 1.0, - "cross_page": true - } - ] - }, - { - "bbox": [ - 69, - 216, - 154, - 230 - ], - "spans": [ - { - "bbox": [ - 69, - 216, - 154, - 230 - ], - "type": "text", - "content": "del copolimero 3.", - "score": 1.0, - "cross_page": true - } - ] - } - ], - "merge_prev": false - } - ] - }, - { - "preproc_blocks": [ - { - "bbox": [ - 67, - 71, - 527, - 231 - ], - "type": "text", - "angle": 0, - "index": 0, - "lines": [ - { - "bbox": [ - 70, - 72, - 524, - 84 - ], - "spans": [ - { - "bbox": [ - 70, - 72, - 524, - 84 - ], - "type": "text", - "content": "di Lewis, potrebbe interferire con il processo di polimerizzazione attraverso due meccanismi", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 93, - 524, - 104 - ], - "spans": [ - { - "bbox": [ - 69, - 93, - 524, - 104 - ], - "type": "text", - "content": "competitivi. In primo luogo, si potrebbe coordinare al FeCl3 formando specie idrate stabili; ciò", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 114, - 524, - 126 - ], - "spans": [ - { - "bbox": [ - 69, - 114, - 524, - 126 - ], - "type": "text", - "content": "saturerebbe la sfera di coordinazione del metallo, riducendone il potenziale ossidativo e", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 134, - 524, - 146 - ], - "spans": [ - { - "bbox": [ - 70, - 134, - 524, - 146 - ], - "type": "text", - "content": "inibendo l'innesco della reazione. In secondo luogo, l'acqua potrebbe causare il quenching degli", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 155, - 524, - 167 - ], - "spans": [ - { - "bbox": [ - 69, - 155, - 524, - 167 - ], - "type": "text", - "content": "intermedi cationico-radicalici in propagazione. 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La completa rimozione dell’ossidante inorganico è un requisito", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 361, - 524, - 374 - ], - "spans": [ - { - "bbox": [ - 69, - 361, - 524, - 374 - ], - "type": "text", - "content": "fondamentale per mantenere l’elettronica del copolimero realizzato: tracce di metalli di", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 382, - 524, - 394 - ], - "spans": [ - { - "bbox": [ - 69, - 382, - 524, - 394 - ], - "type": "text", - "content": "transizione all’interno del backbone polimerico abbatterebbero la mobilità dei portatori di", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 403, - 523, - 415 - ], - "spans": [ - { - "bbox": [ - 70, - 403, - 523, - 415 - ], - "type": "text", - "content": "carica e spegnerebbero la fluorescenza del materiale. Per monitorare l'efficacia dell'estrazione,", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 423, - 524, - 436 - ], - "spans": [ - { - "bbox": [ - 69, - 423, - 524, - 436 - ], - "type": "text", - "content": "le acque di lavaggio sono state sottoposte al saggio del tiocianato. L'aggiunta dello ione SCN-", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 444, - 523, - 456 - ], - "spans": [ - { - "bbox": [ - 70, - 444, - 523, - 456 - ], - "type": "text", - "content": "genera, in presenza di ioni Fe3+, un complesso di coordinazione caratterizzato da un'intensa", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 465, - 524, - 477 - ], - "spans": [ - { - "bbox": [ - 69, - 465, - 524, - 477 - ], - "type": "text", - "content": "colorazione rossa. I lavaggi acidi sono stati ripetuti fino all'ottenimento di un saggio negativo", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 486, - 523, - 497 - ], - "spans": [ - { - "bbox": [ - 69, - 486, - 523, - 497 - ], - "type": "text", - "content": "(soluzione incolore), a riprova della totale purificazione del sistema organico dai residui", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 507, - 122, - 519 - ], - "spans": [ - { - "bbox": [ - 69, - 507, - 122, - 519 - ], - "type": "text", - "content": "inorganici.", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - }, - { - "bbox": [ - 67, - 526, - 527, - 645 - ], - "type": "text", - "angle": 0, - "index": 3, - "lines": [ - { - "bbox": [ - 69, - 527, - 524, - 539 - ], - "spans": [ - { - "bbox": [ - 69, - 527, - 524, - 539 - ], - "type": "text", - "content": "L'ultimo lavaggio con una soluzione acquosa mezza satura di cloruro di sodio (NaCl) sfrutta", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 68, - 546, - 524, - 560 - ], - "spans": [ - { - "bbox": [ - 68, - 546, - 524, - 560 - ], - "type": "text", - "content": "l'elevata forza ionica del sale per massimizzare l'effetto di salting-out: l'ambiente acquoso salino", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 568, - 524, - 581 - ], - "spans": [ - { - "bbox": [ - 69, - 568, - 524, - 581 - ], - "type": "text", - "content": "favorisce l'estrazione dell'acqua parzialmente disciolta nel solvente organico. 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Copolimeromoli DPP 2moli 3HT% DPP teorica (mol/mol)% DPP reale (mol/mol)
3a0.20.82025.2
3b0.50.55032.6
3c0.80.28035.3
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Copolimeromoli DPP 2moli 3HT% DPP teorica (mol/mol)% DPP reale (mol/mol)
3a0.20.82025.2
3b0.50.55032.6
3c0.80.28035.3
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Copolimero\\lambda_{\\text{max, asb (nm)}}\\lambda_{\\text{max, ecc (nm)}}Stokes shift (nm)
3a5405477
3b5445506
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], - "spans": [ - { - "bbox": [ - 70, - 155, - 524, - 167 - ], - "type": "text", - "content": "fisico del core dichetopirrolopirrolico. Si nota come tutti i campioni presentino uno Stokes shift", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 175, - 524, - 187 - ], - "spans": [ - { - "bbox": [ - 70, - 175, - 524, - 187 - ], - "type": "text", - "content": "estremamente ridotto: questa forte sovrapposizione tra le bande di assorbimento ed emissione", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 68, - 195, - 524, - 208 - ], - "spans": [ - { - "bbox": [ - 68, - 195, - 524, - 208 - ], - "type": "text", - "content": "è indicativa di una notevole rigidità strutturale dello scheletro polimerico, il quale subisce una", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 217, - 523, - 229 - ], - "spans": [ - { - "bbox": [ - 69, - 217, - 523, - 229 - ], - "type": "text", - "content": "minima riorganizzazione conformazionale nel passaggio dallo stato fondamentale a quello", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 238, - 112, - 250 - ], - "spans": [ - { - "bbox": [ - 69, - 238, - 112, - 250 - ], - "type": "text", - "content": "eccitato.", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - }, - { - "type": "table", - "bbox": [ - 114, - 283, - 478, - 375 - ], - "blocks": [ - { - "bbox": [ - 193, - 268, - 401, - 280 - ], - "type": "table_caption", - "angle": 0, - "index": 1, - "lines": [ - { - "bbox": [ - 195, - 269, - 399, - 279 - ], - "spans": [ - { - "bbox": [ - 195, - 269, - 399, - 279 - ], - "type": "text", - "content": "Tabella 7 - dati spettroscopici dei copolimeri sintetizzati", - "score": 1.0 - } - ] - } - ] - }, - { - "bbox": [ - 114, - 283, - 478, - 375 - ], - "type": "table_body", - "angle": 0, - "lines": [ - { - "bbox": [ - 114, - 283, - 478, - 375 - ], - "spans": [ - { - "bbox": [ - 114, - 283, - 478, - 375 - ], - "type": "table", - "html": "
Copolimero\\lambda_{\\text{max, asb (nm)}}\\lambda_{\\text{max, ecc (nm)}}Stokes shift (nm)
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3c54255210
", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/2450b4ec-54d1-41b5-85f2-f45c8f45084f/dc906c2beb12c30ef0ff5cdc833e911a12ac273ba4d08e0300d6e6061388ac5d.jpg" - } - ] - } - ], - "index": 2 - } - ], - "index": 2 - }, - { - "bbox": [ - 67, - 417, - 527, - 578 - ], - "type": "text", - "angle": 0, - "index": 3, - "lines": [ - { - "bbox": [ - 70, - 419, - 524, - 431 - ], - "spans": [ - { - "bbox": [ - 70, - 419, - 524, - 431 - ], - "type": "text", - "content": "Tuttavia, sebbene in soluzione diluita i copolimeri mantengano queste eccellenti caratteristiche", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 440, - 524, - 451 - ], - "spans": [ - { - "bbox": [ - 70, - 440, - 524, - 451 - ], - "type": "text", - "content": "emissive, il loro comportamento allo stato solido risulta drasticamente differente. Come", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 461, - 523, - 473 - ], - "spans": [ - { - "bbox": [ - 70, - 461, - 523, - 473 - ], - "type": "text", - "content": "tipicamente si osserva nei sistemi �-coniugati altamente planari, la deposizione allo stato solido", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 481, - 524, - 493 - ], - "spans": [ - { - "bbox": [ - 69, - 481, - 524, - 493 - ], - "type": "text", - "content": "favorisce una forte interazione intermolecolare. L'intenso impaccamento delle catene porta alla", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 502, - 524, - 514 - ], - "spans": [ - { - "bbox": [ - 69, - 502, - 524, - 514 - ], - "type": "text", - "content": "formazione di aggregati che disattivano i fluorofori attraverso percorsi di decadimento non", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 523, - 524, - 534 - ], - "spans": [ - { - "bbox": [ - 69, - 523, - 524, - 534 - ], - "type": "text", - "content": "radiativo. Questo effetto è visivamente confermato osservando i campioni polimerici depositati", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 543, - 524, - 555 - ], - "spans": [ - { - "bbox": [ - 69, - 543, - 524, - 555 - ], - "type": "text", - "content": "su vetrino: esposti all'illuminazione di una lampada UV (Figura 61), i film non mostrano alcuna", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 565, - 264, - 576 - ], - "spans": [ - { - "bbox": [ - 70, - 565, - 264, - 576 - ], - "type": "text", - "content": "emissione apprezzabile allo stato solido.", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - }, - { - "type": "image", - "bbox": [ - 108, - 595, - 229, - 719 - ], - "blocks": [ - { - "bbox": [ - 108, - 595, - 229, - 719 - ], - "type": "image_body", - "angle": 0, - "lines": [ - { - "bbox": [ - 108, - 595, - 229, - 719 - ], - "spans": [ - { - "bbox": [ - 108, - 595, - 229, - 719 - ], - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/2450b4ec-54d1-41b5-85f2-f45c8f45084f/295f958dc5bc25492bb41127bf21d1ef1d5ba7268f652ab7432d268fa341daa2.jpg" - } - ] - } - ], - "index": 4 - } - ], - "index": 4 - }, - { - "type": "image", - "bbox": [ - 238, - 595, - 356, - 719 - ], - "blocks": [ - { - "bbox": [ - 238, - 595, - 356, - 719 - ], - "type": "image_body", - "angle": 0, - "lines": [ - { - "bbox": [ - 238, - 595, - 356, - 719 - ], - "spans": [ - { - "bbox": [ - 238, - 595, - 356, - 719 - ], - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/2450b4ec-54d1-41b5-85f2-f45c8f45084f/9f2325e919b4f36932bf30c91ec89129de1e34945b6ba9b1255e8a59575ae7a2.jpg" - } - ] - } - ], - "index": 5 - } - ], - "index": 5 - }, - { - "type": "image", - "bbox": [ - 364, - 596, - 485, - 719 - ], - "blocks": [ - { - "bbox": [ - 364, - 596, - 485, - 719 - ], - "type": "image_body", - "angle": 0, - "lines": [ - { - "bbox": [ - 364, - 596, - 485, - 719 - ], - "spans": [ - { - "bbox": [ - 364, - 596, - 485, - 719 - ], - "type": "image", - "image_path": "https://cdn-mineru.openxlab.org.cn/result/2026-10-09/2450b4ec-54d1-41b5-85f2-f45c8f45084f/5e1a2c9d56c2b4d44c1175bc8c4db711a5d31d7d50cdc1638b30642000cd9a12.jpg" - } - ] - } - ], - "index": 6 - }, - { - "bbox": [ - 135, - 728, - 459, - 740 - ], - "type": "image_caption", - "angle": 0, - "index": 7, - "lines": [ - { - "bbox": [ - 136, - 729, - 458, - 739 - ], - "spans": [ - { - "bbox": [ - 136, - 729, - 458, - 739 - ], - "type": "text", - "content": "Figura 61 -film solidi dei copolimeri sotto lampada UV, in ordine copolimero 3a, 3b, 3c", - "score": 1.0 - } - ] - } - ] - } - ], - "index": 6 - } - ] - }, - { - "preproc_blocks": [ - { - "bbox": [ - 67, - 71, - 526, - 189 - ], - "type": "text", - "angle": 0, - "index": 0, - "lines": [ - { - "bbox": [ - 69, - 72, - 524, - 84 - ], - "spans": [ - { - "bbox": [ - 69, - 72, - 524, - 84 - ], - "type": "text", - "content": "Proprio questa tendenza all'aggregazione, e al conseguente quenching emissivo nei film solidi,", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 92, - 524, - 105 - ], - "spans": [ - { - "bbox": [ - 69, - 92, - 524, - 105 - ], - "type": "text", - "content": "rappresenta la principale criticità per l'impiego di tali sistemi lineari in dispositivi", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 113, - 524, - 125 - ], - "spans": [ - { - "bbox": [ - 69, - 113, - 524, - 125 - ], - "type": "text", - "content": "optoelettronici. Per superare questo limite strutturale è necessario sfavorire l'avvicinamento", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 130, - 525, - 146 - ], - "spans": [ - { - "bbox": [ - 69, - 134, - 304, - 146 - ], - "type": "text", - "content": "incontrollato delle catene principali coniugate.", - "score": 1.0 - }, - { - "bbox": [ - 304, - 130, - 315, - 146 - ], - "type": "inline_equation", - "content": "\\dot { \\mathrm { ~ E ~ } }", - "score": 0.4745 - }, - { - "bbox": [ - 315, - 134, - 525, - 146 - ], - "type": "text", - "content": "in quest'ottica che si è reso necessario il", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 155, - 524, - 168 - ], - "spans": [ - { - "bbox": [ - 69, - 155, - 524, - 168 - ], - "type": "text", - "content": "passaggio a un design macromolecolare più complesso, che giustifica la progettazione e la", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 175, - 282, - 187 - ], - "spans": [ - { - "bbox": [ - 70, - 175, - 282, - 187 - ], - "type": "text", - "content": "sintesi di un'architettura di tipo bottle-brush.", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - }, - { - "bbox": [ - 67, - 195, - 525, - 231 - ], - "type": "text", - "angle": 0, - "index": 1, - "lines": [ - { - "bbox": [ - 70, - 197, - 523, - 208 - ], - "spans": [ - { - "bbox": [ - 70, - 197, - 523, - 208 - ], - "type": "text", - "content": "Successivamente, i copolimeri sono stati caratterizzati mediante cromatografia a permeazione", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 216, - 381, - 227 - ], - "spans": [ - { - "bbox": [ - 70, - 216, - 381, - 227 - ], - "type": "text", - "content": "di gel (GPC) per determinare la distribuzione dei pesi molecolari", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - }, - { - "bbox": [ - 67, - 236, - 526, - 336 - ], - "type": "text", - "angle": 0, - "index": 2, - "lines": [ - { - "bbox": [ - 69, - 238, - 524, - 250 - ], - "spans": [ - { - "bbox": [ - 69, - 238, - 524, - 250 - ], - "type": "text", - "content": "I risultati dell'analisi cromatografica riportati in Tabella 8 evidenziano masse molecolari medie", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 257, - 525, - 272 - ], - "spans": [ - { - "bbox": [ - 69, - 257, - 114, - 272 - ], - "type": "text", - "content": "numerali", - "score": 1.0 - }, - { - "bbox": [ - 115, - 258, - 139, - 272 - ], - "type": "inline_equation", - "content": "( \\overline { { M _ { n } } } )", - "score": 0.8945 - }, - { - "bbox": [ - 139, - 257, - 525, - 272 - ], - "type": "text", - "content": "comprese tra circa 1400 e 2150 Da per i copolimeri sintetizzati. 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CopolimeroMassa molecolare media numerica \\overline{M_n} (Da)Massa molecolare media ponderale \\overline{M_w} (Da)Polidispersità (PD)
3a214955262,571
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CopolimeroMassa molecolare media numerica \\overline{M_n} (Da)Massa molecolare media ponderale \\overline{M_w} (Da)Polidispersità (PD)
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La scelta", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 615, - 524, - 627 - ], - "spans": [ - { - "bbox": [ - 69, - 615, - 524, - 627 - ], - "type": "text", - "content": "di questo specifico non-solvente è dettata dalle differenti solubilità delle specie in soluzione:", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 635, - 524, - 647 - ], - "spans": [ - { - "bbox": [ - 69, - 635, - 524, - 647 - ], - "type": "text", - "content": "mentre l'ε-caprolattone residuo e le altre specie a basso peso molecolare presentano un'elevata", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 656, - 523, - 668 - ], - "spans": [ - { - "bbox": [ - 70, - 656, - 523, - 668 - ], - "type": "text", - "content": "affinità per il metanolo, il copolimero ad alto peso molecolare vi risulta insolubile. 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Il polimero così", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 68, - 719, - 394, - 730 - ], - "spans": [ - { - "bbox": [ - 68, - 719, - 394, - 730 - ], - "type": "text", - "content": "precipitato è stato successivamente recuperato mediante filtrazione.", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - } - ] - }, - { - "preproc_blocks": [ - { - "bbox": [ - 66, - 71, - 527, - 293 - ], - "type": "text", - "angle": 0, - "index": 0, - "lines": [ - { - "bbox": [ - 70, - 73, - 524, - 84 - ], - "spans": [ - { - "bbox": [ - 70, - 73, - 524, - 84 - ], - "type": "text", - "content": "Allo scopo di valutare in modo sistematico l'influenza della lunghezza delle catene laterali sulle", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 93, - 524, - 105 - ], - "spans": [ - { - "bbox": [ - 69, - 93, - 524, - 105 - ], - "type": "text", - "content": "proprietà finali del materiale, sono state preparate due serie di polimeri bottle brush. Queste", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 114, - 524, - 126 - ], - "spans": [ - { - "bbox": [ - 69, - 114, - 524, - 126 - ], - "type": "text", - "content": "serie sono state ottenute impiegando rispettivamente i copolimeri 3b e 3c in qualità di", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 134, - 524, - 146 - ], - "spans": [ - { - "bbox": [ - 69, - 134, - 524, - 146 - ], - "type": "text", - "content": "macroiniziatori. Sebbene fosse stato sintetizzato anche un terzo copolimero 3a, il suo impiego", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 68, - 154, - 524, - 167 - ], - "spans": [ - { - "bbox": [ - 68, - 154, - 524, - 167 - ], - "type": "text", - "content": "per le successive fasi di grafting è stato scartato a causa della scarsa efficienza della sua via", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 175, - 525, - 187 - ], - "spans": [ - { - "bbox": [ - 69, - 175, - 525, - 187 - ], - "type": "text", - "content": "sintetica. Nello specifico, le basse rese di reazione e le difficoltà incontrate nel work-up per", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 196, - 524, - 208 - ], - "spans": [ - { - "bbox": [ - 69, - 196, - 524, - 208 - ], - "type": "text", - "content": "l'isolamento del prodotto puro portavano a notevoli perdite di materiale. Inoltre, dal punto di", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 68, - 216, - 524, - 230 - ], - "spans": [ - { - "bbox": [ - 68, - 216, - 524, - 230 - ], - "type": "text", - "content": "vista dell’efficienza di processo, l'isolamento di quantità utili di questo copolimero avrebbe", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 68, - 236, - 525, - 250 - ], - "spans": [ - { - "bbox": [ - 68, - 236, - 525, - 250 - ], - "type": "text", - "content": "richiesto volumi di solventi e costi di reagenti molto elevati. 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Seguendo questo approccio, per", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 361, - 525, - 374 - ], - "spans": [ - { - "bbox": [ - 70, - 361, - 525, - 374 - ], - "type": "text", - "content": "ciascuno dei due precursori copolimerici sono stati sintetizzati tre differenti polimeri dotate di", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 381, - 521, - 395 - ], - "spans": [ - { - "bbox": [ - 69, - 381, - 521, - 395 - ], - "type": "text", - "content": "catene laterali in PCL con pesi molecolari di circa 1500 Da, 5000 Da e 10000 Da (Tabella 9).", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - }, - { - "type": "table", - "bbox": [ - 68, - 428, - 523, - 577 - ], - "blocks": [ - { - "bbox": [ - 173, - 413, - 420, - 425 - ], - "type": "table_caption", - "angle": 0, - "index": 2, - "lines": [ - { - "bbox": [ - 176, - 415, - 418, - 423 - ], - "spans": [ - { - "bbox": [ - 176, - 415, - 418, - 423 - ], - "type": "text", - "content": "Tabella 9 - lunghezza delle catene in PCL nei polimeri bottle brush", - "score": 1.0 - } - ] - } - ] - }, - { - "bbox": [ - 68, - 428, - 523, - 577 - ], - "type": "table_body", - "angle": 0, - "lines": [ - { - "bbox": [ - 68, - 428, - 523, - 577 - ], - "spans": [ - { - "bbox": [ - 68, - 428, - 523, - 577 - ], - "type": "table", - "html": "
CopolimeroPolimero bottle brushLunghezza catene di PCL (Da)
3b3.1b1500
3.2b5000
3.3b10000
3c3.1c1500
3.2c5000
3.3c10000
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CopolimeroPolimero bottle brushLunghezza catene di PCL (Da)
3b3.1b1500
3.2b5000
3.3b10000
3c3.1c1500
3.2c5000
3.3c10000
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Ponendo alla base la traccia del relativo copolimero macroiniziatore, è possibile", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 437, - 523, - 449 - ], - "spans": [ - { - "bbox": [ - 70, - 437, - 523, - 449 - ], - "type": "text", - "content": "apprezzare in modo diretto le variazioni spettrali indotte dalle catene laterali di policaprolattone.", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 458, - 523, - 470 - ], - "spans": [ - { - "bbox": [ - 69, - 458, - 523, - 470 - ], - "type": "text", - "content": "L'analisi comparativa conferma chiaramente il successo della reazione. 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Spicca in particolar modo la comparsa di un picco molto stretto e ad alta intensità", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 600, - 524, - 615 - ], - "spans": [ - { - "bbox": [ - 70, - 603, - 146, - 613 - ], - "type": "text", - "content": "centrato a circa", - "score": 1.0 - }, - { - "bbox": [ - 150, - 600, - 201, - 615 - ], - "type": "inline_equation", - "content": "1 7 2 0 \\ \\mathrm { c m } ^ { - 1 }", - "score": 0.7611 - }, - { - "bbox": [ - 201, - 602, - 524, - 615 - ], - "type": "text", - "content": ", attribuibile allo stretching del gruppo carbonilico (C=O) estereo", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 624, - 524, - 634 - ], - "spans": [ - { - "bbox": [ - 70, - 624, - 524, - 634 - ], - "type": "text", - "content": "delle unità di caprolattone. 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3.3c55356411
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3.2b17302227371,314
3.3b21269263281,238
3.1c13999182191,301
3.2c19119243761,275
3.3c14445195211,351
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PolimeroPeso Molecolare teorico (Da)Peso Molecolare da ^{1}H-NMR (Da)
3.1b65008900
3.2b1800020500
3.3b3450088000
3.1c1000018200
3.2c2850035500
3.3c5500041300
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PolimeroE_{onset}^{ox} (V)E_{onset}^{red} (V)HOMO (eV)LUMO (eV)Bandgap (eV)
3.1.b-0,183-1,22-4,617-3,5801,037
3.2.b-0,175-1,273-4,625-3,5271,098
3.3.b-0,17-1,202-4,630-3,5981,032
3.1.c-0,0259-1,547-4,774-3,2531,521
3.2.c-0,112-1,531-4,688-3,2691,419
3.3.c-0,321-1,25-4,479-3,5500,929
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PolimeroE_{onset}^{ox} (V)E_{onset}^{red} (V)HOMO (eV)LUMO (eV)Bandgap (eV)
3.1.b-0,183-1,22-4,617-3,5801,037
3.2.b-0,175-1,273-4,625-3,5271,098
3.3.b-0,17-1,202-4,630-3,5981,032
3.1.c-0,0259-1,547-4,774-3,2531,521
3.2.c-0,112-1,531-4,688-3,2691,419
3.3.c-0,321-1,25-4,479-3,5500,929
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Questo approccio si è rivelato particolarmente", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 600, - 524, - 613 - ], - "spans": [ - { - "bbox": [ - 69, - 600, - 524, - 613 - ], - "type": "text", - "content": "vantaggioso rispetto ai canonici accoppiamenti incrociati mediati da palladio, eliminando la", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 621, - 524, - 633 - ], - "spans": [ - { - "bbox": [ - 69, - 621, - 524, - 633 - ], - "type": "text", - "content": "necessità di stadi di pre-funzionalizzazione e operando in condizioni termodinamiche blande.", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 641, - 524, - 653 - ], - "spans": [ - { - "bbox": [ - 69, - 641, - 524, - 653 - ], - "type": "text", - "content": "La sintesi di tre differenti copolimeri statistici a rapporto co-monomerico variabile (3a, 3b e", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 662, - 524, - 674 - ], - "spans": [ - { - "bbox": [ - 69, - 662, - 524, - 674 - ], - "type": "text", - "content": "3c) ha confermato la versatilità della metodica, permettendo di ottenere materiali processabili", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 683, - 523, - 695 - ], - "spans": [ - { - "bbox": [ - 69, - 683, - 523, - 695 - ], - "type": "text", - "content": "con pesi molecolari compresi tra circa 1400 e 2150 Da e un intervallo di lavorabilità termica", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 703, - 524, - 716 - ], - "spans": [ - { - "bbox": [ - 69, - 704, - 339, - 716 - ], - "type": "text", - "content": "adeguato, caratterizzato da transizioni vetrose intorno", - "score": 1.0 - }, - { - "bbox": [ - 342, - 703, - 396, - 715 - ], - "type": "inline_equation", - "content": "\\mathrm { ~ a ~ - ~ } 1 0 ~ ^ { \\circ } \\mathrm { C }", - "score": 0.8189 - }, - { - "bbox": [ - 401, - 703, - 524, - 716 - ], - "type": "text", - "content": "e temperature di fusione", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 724, - 158, - 737 - ], - "spans": [ - { - "bbox": [ - 69, - 724, - 122, - 737 - ], - "type": "text", - "content": "superiori a", - "score": 1.0 - }, - { - "bbox": [ - 124, - 724, - 158, - 736 - ], - "type": "inline_equation", - "content": "1 1 0 ~ ^ { \\circ } \\mathrm { C }", - "score": 0.7958 - } - ] - } - ], - "merge_prev": false - } - ], - "discarded_blocks": [ - { - "bbox": [ - 510, - 785, - 525, - 797 - ], - "type": "page_number", - "angle": 0, - "index": 3, - "lines": [ - { - "bbox": [ - 510, - 786, - 525, - 799 - ], - "spans": [ - { - "bbox": [ - 510, - 786, - 525, - 799 - ], - "type": "text", - "content": "99", - "score": 1.0 - } - ] - } - ] - } - ], - "page_size": [ - 595, - 841 - ], - "page_idx": 104, - "para_blocks": [ - { - "bbox": [ - 67, - 72, - 177, - 89 - ], - "type": "title", - "angle": 0, - "index": 0, - "lines": [ - { - "bbox": [ - 68, - 72, - 176, - 89 - ], - "spans": [ - { - "bbox": [ - 68, - 72, - 176, - 89 - ], - "type": "text", - "content": "5. 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La naturale propensione dei sistemi", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 206, - 524, - 218 - ], - "spans": [ - { - "bbox": [ - 69, - 206, - 395, - 218 - ], - "type": "text", - "content": "planari coniugati a instaurare intense interazioni supramolecolari di", - "score": 1.0 - }, - { - "bbox": [ - 396, - 206, - 414, - 217 - ], - "type": "inline_equation", - "content": "\\pi { - } \\pi", - "score": 0.5821 - }, - { - "bbox": [ - 415, - 206, - 524, - 218 - ], - "type": "text", - "content": "stacking porta infatti a", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 227, - 524, - 238 - ], - "spans": [ - { - "bbox": [ - 70, - 227, - 524, - 238 - ], - "type": "text", - "content": "una drastica dissipazione non radiativa dell’energia eccitonica allo stato solido. Per ovviare a", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 248, - 524, - 259 - ], - "spans": [ - { - "bbox": [ - 70, - 248, - 524, - 259 - ], - "type": "text", - "content": "questo limite, la strategia adottata si è basata sulla realizzazione di copolimeri bottle brush, nei", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 268, - 524, - 280 - ], - "spans": [ - { - "bbox": [ - 70, - 268, - 524, - 280 - ], - "type": "text", - "content": "quali l'accrescimento di catene polimeriche laterali flessibili lungo uno scheletro elettro- e", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 288, - 523, - 301 - ], - "spans": [ - { - "bbox": [ - 69, - 288, - 523, - 301 - ], - "type": "text", - "content": "fotoattivo è stato sfruttato come spaziatore sterico per modulare l'impaccamento", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 310, - 459, - 321 - ], - "spans": [ - { - "bbox": [ - 70, - 310, - 459, - 321 - ], - "type": "text", - "content": "intermolecolare, preservando al contempo le proprietà elettroniche del backbone.", - "score": 1.0 - } - ] - } - ], - "merge_prev": false - }, - { - "bbox": [ - 66, - 328, - 527, - 739 - ], - "type": "text", - "angle": 0, - "index": 2, - "lines": [ - { - "bbox": [ - 69, - 330, - 524, - 342 - ], - "spans": [ - { - "bbox": [ - 69, - 330, - 524, - 342 - ], - "type": "text", - "content": "Dal punto di vista sintetico, il percorso intrapreso ha dimostrato la piena efficacia e", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 351, - 524, - 363 - ], - "spans": [ - { - "bbox": [ - 69, - 351, - 524, - 363 - ], - "type": "text", - "content": "riproducibilità di una strategia basata sull'impiego di monomeri ortogonali e multifunzionali", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 371, - 524, - 382 - ], - "spans": [ - { - "bbox": [ - 69, - 371, - 524, - 382 - ], - "type": "text", - "content": "derivati dal dichetopirrolopirrolo (DPP). In primo luogo, la reazione di ciclizzazione tra il 2-", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 391, - 524, - 404 - ], - "spans": [ - { - "bbox": [ - 69, - 391, - 524, - 404 - ], - "type": "text", - "content": "cianotiofene e il diisopropil succinato ha consentito di isolare con successo il fluoroforo", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 412, - 524, - 423 - ], - "spans": [ - { - "bbox": [ - 70, - 413, - 508, - 423 - ], - "type": "text", - "content": "tetraciclico 1. La successiva funzionalizzazione mediante �-alchilazione nucleofila con", - "score": 1.0 - }, - { - "bbox": [ - 512, - 412, - 524, - 423 - ], - "type": "inline_equation", - "content": "6 \\textdegree", - "score": 0.4583 - } - ] - }, - { - "bbox": [ - 70, - 434, - 524, - 445 - ], - "spans": [ - { - "bbox": [ - 70, - 434, - 524, - 445 - ], - "type": "text", - "content": "bromo-1-esanolo ha portato all’ottenimento del monomero chiave bis-alchilato (composto 2),", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 454, - 524, - 469 - ], - "spans": [ - { - "bbox": [ - 69, - 456, - 236, - 469 - ], - "type": "text", - "content": "confermato per via spettroscopica", - "score": 1.0 - }, - { - "bbox": [ - 239, - 454, - 336, - 468 - ], - "type": "inline_equation", - "content": "( ^ { 1 } \\mathrm { H - N M R } \\mathrm { ~ e ~ } \\mathrm { F T - I R } )", - "score": 0.8457 - }, - { - "bbox": [ - 336, - 456, - 524, - 468 - ], - "type": "text", - "content": ". Tale monomero ha esibito la duplice", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 476, - 524, - 488 - ], - "spans": [ - { - "bbox": [ - 69, - 476, - 524, - 488 - ], - "type": "text", - "content": "funzionalità ricercata: la presenza degli eterocicli tiofenici ha fornito i siti reattivi per", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 497, - 524, - 509 - ], - "spans": [ - { - "bbox": [ - 69, - 497, - 524, - 509 - ], - "type": "text", - "content": "l'accrescimento della catena principale semiconduttrice, mentre i gruppi ossidrilici primari", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 518, - 524, - 529 - ], - "spans": [ - { - "bbox": [ - 69, - 518, - 524, - 529 - ], - "type": "text", - "content": "terminali hanno svolto il ruolo di iniziatori indipendenti per la successiva fase di innesto. La", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 68, - 538, - 524, - 550 - ], - "spans": [ - { - "bbox": [ - 68, - 538, - 524, - 550 - ], - "type": "text", - "content": "sintesi dello scheletro polimerico coniugato è stata condotta mediante polimerizzazione", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 559, - 524, - 571 - ], - "spans": [ - { - "bbox": [ - 69, - 559, - 524, - 571 - ], - "type": "text", - "content": "ossidativa diretta mediata da cloruro ferrico in presenza di nitrometano, accoppiando il", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 580, - 524, - 592 - ], - "spans": [ - { - "bbox": [ - 69, - 580, - 524, - 592 - ], - "type": "text", - "content": "monomero di DPP con il 3-esiltiofene (3HT). Questo approccio si è rivelato particolarmente", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 600, - 524, - 613 - ], - "spans": [ - { - "bbox": [ - 69, - 600, - 524, - 613 - ], - "type": "text", - "content": "vantaggioso rispetto ai canonici accoppiamenti incrociati mediati da palladio, eliminando la", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 621, - 524, - 633 - ], - "spans": [ - { - "bbox": [ - 69, - 621, - 524, - 633 - ], - "type": "text", - "content": "necessità di stadi di pre-funzionalizzazione e operando in condizioni termodinamiche blande.", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 641, - 524, - 653 - ], - "spans": [ - { - "bbox": [ - 69, - 641, - 524, - 653 - ], - "type": "text", - "content": "La sintesi di tre differenti copolimeri statistici a rapporto co-monomerico variabile (3a, 3b e", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 662, - 524, - 674 - ], - "spans": [ - { - "bbox": [ - 69, - 662, - 524, - 674 - ], - "type": "text", - "content": "3c) ha confermato la versatilità della metodica, permettendo di ottenere materiali processabili", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 683, - 523, - 695 - ], - "spans": [ - { - "bbox": [ - 69, - 683, - 523, - 695 - ], - "type": "text", - "content": "con pesi molecolari compresi tra circa 1400 e 2150 Da e un intervallo di lavorabilità termica", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 703, - 524, - 716 - ], - "spans": [ - { - "bbox": [ - 69, - 704, - 339, - 716 - ], - "type": "text", - "content": "adeguato, caratterizzato da transizioni vetrose intorno", - "score": 1.0 - }, - { - "bbox": [ - 342, - 703, - 396, - 715 - ], - "type": "inline_equation", - "content": "\\mathrm { ~ a ~ - ~ } 1 0 ~ ^ { \\circ } \\mathrm { C }", - "score": 0.8189 - }, - { - "bbox": [ - 401, - 703, - 524, - 716 - ], - "type": "text", - "content": "e temperature di fusione", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 724, - 158, - 737 - ], - "spans": [ - { - "bbox": [ - 69, - 724, - 122, - 737 - ], - "type": "text", - "content": "superiori a", - "score": 1.0 - }, - { - "bbox": [ - 124, - 724, - 158, - 736 - ], - "type": "inline_equation", - "content": "1 1 0 ~ ^ { \\circ } \\mathrm { C }", - "score": 0.7958 - } - ] - } - ], - "merge_prev": false - } - ] - }, - { - "preproc_blocks": [ - { - "bbox": [ - 66, - 71, - 527, - 377 - ], - "type": "text", - "angle": 0, - "index": 0, - "lines": [ - { - "bbox": [ - 69, - 72, - 524, - 84 - ], - "spans": [ - { - "bbox": [ - 69, - 72, - 524, - 84 - ], - "type": "text", - "content": "L’accrescimento delle architetture bottle brush a partire dai macroiniziatori 3b e 3c è stato", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 93, - 523, - 105 - ], - "spans": [ - { - "bbox": [ - 69, - 93, - 523, - 105 - ], - "type": "text", - "content": "realizzato mediante polimerizzazione ad apertura d'anello (ROP) dell' �-caprolattone,", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 114, - 524, - 126 - ], - "spans": [ - { - "bbox": [ - 69, - 114, - 524, - 126 - ], - "type": "text", - "content": "catalizzata da ottanoato di stagno. Attraverso la modulazione del rapporto molare tra monomero", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 135, - 524, - 147 - ], - "spans": [ - { - "bbox": [ - 69, - 135, - 524, - 147 - ], - "type": "text", - "content": "ciclico e siti ossidrilici pendenti, sono state sintetizzate con successo due serie di copolimeri a", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 155, - 524, - 167 - ], - "spans": [ - { - "bbox": [ - 69, - 155, - 524, - 167 - ], - "type": "text", - "content": "spazzola con catene laterali di PCL a pesi molecolari nominali crescenti (1500, 5000 e 10000", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 176, - 524, - 188 - ], - "spans": [ - { - "bbox": [ - 69, - 176, - 524, - 188 - ], - "type": "text", - "content": "Da). L'avvenuta reazione di innesto è stata verificata tramite FT-IR, registrando la completa", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 196, - 524, - 208 - ], - "spans": [ - { - "bbox": [ - 69, - 196, - 524, - 208 - ], - "type": "text", - "content": "scomparsa della banda associata agli ossidrili terminali e la concomitante comparsa dell'intenso", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 216, - 524, - 230 - ], - "spans": [ - { - "bbox": [ - 70, - 219, - 312, - 229 - ], - "type": "text", - "content": "assorbimento carbonilico estereo del PCL a circa", - "score": 1.0 - }, - { - "bbox": [ - 315, - 216, - 372, - 230 - ], - "type": "inline_equation", - "content": "1 7 2 0 \\mathrm { c m } ^ { - 1 }", - "score": 0.6265 - }, - { - "bbox": [ - 372, - 218, - 524, - 230 - ], - "type": "text", - "content": ". L'indagine condotta mediante", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 239, - 524, - 251 - ], - "spans": [ - { - "bbox": [ - 70, - 239, - 524, - 251 - ], - "type": "text", - "content": "cromatografia a permeazione di gel (GPC) ha evidenziato indici di dispersità contenuti (1.23–", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 70, - 259, - 524, - 271 - ], - "spans": [ - { - "bbox": [ - 70, - 259, - 524, - 271 - ], - "type": "text", - "content": "1.52). Inoltre, la marcata contrazione del volume idrodinamico in soluzione rilevata rispetto ai", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 280, - 525, - 292 - ], - "spans": [ - { - "bbox": [ - 69, - 280, - 525, - 292 - ], - "type": "text", - "content": "pesi teorici lineari ha costituito una prova dell'ottenimento di macromolecole ramificate a", - "score": 1.0 - } - ] - }, - { - "bbox": [ - 69, - 301, - 524, - 313 - ], - "spans": [ - { - "bbox": [ - 69, - 301, - 524, - 313 - ], - "type": "text", - "content": "densità elevata e struttura altamente compatta. 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