davideandClaude Sonnet 5.5
6412cb2347
- tesi.md rigenerato dal docx (1446 righe); aggiunto raw/tesi.docx - 4 nuove immagini (Fig. 52, Fig. 76, due schemi di §3.2); immagini.json rinumerato e rimappato (80 figure) - bibliografia.json e schede in fonti/ riallineati (63 riferimenti, 4 nuovi) Co-Authored-By: Claude Sonnet 5.5 <noreply@anthropic.com>
141 lines
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141 lines
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---
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id: 31
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anchor: ref-31
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stato: verificata
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doi: 10.1021/jo2003117
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url: https://doi.org/10.1021/jo2003117
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anno: 2011
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rivista: "The Journal of Organic Chemistry"
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volume: "76"
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pagine: "2426-2432"
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editore: "American Chemical Society (ACS)"
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tipo: journal-article
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autori: ["Hannah Bürckstümmer", "Annike Weißenstein", "David Bialas", "Frank Würthner"]
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accesso: closed
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licenza: null
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pmcid: null
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citata_da: 183
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argomenti: ["Organic Electronics and Photovoltaics", "Synthesis and Properties of Aromatic Compounds", "Organic Light-Emitting Diodes Research"]
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parole_chiave: ["diketopyrrolopyrrole", "bithiophene", "palladium-catalyzed cross-coupling", "boronic esters", "peripheral substituent effects", "near-infrared absorption", "fluorescence", "electrochemical properties", "redox properties", "organic solar cells"]
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contenuto_letto: solo_abstract
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tags: [fonte, bibliografia]
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cited_in_sections: [1.1.2]
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---
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# [31] Bürckstümmer (2011) - Synthesis and Characterization of Optical and Redox Properties of Bithiophene-Functionalized Diketopyrrolopyrrole Chromophores
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## Come è scritta nella tesi
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Bürckstümmer, H., Weissenstein, A., Bialas, D. & Würthner, F. Synthesis and Characterization of Optical and Redox Properties of Bithiophene-Functionalized Diketopyrrolopyrrole Chromophores. *J. Org. Chem.* **76**, 2426–2432 (2011).
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## Scheda bibliografica
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**Citazione completa:** Bürckstümmer, H.; Weissenstein, A.; Bialas, D.; Würthner, F. Synthesis and Characterization of Optical and Redox Properties of Bithiophene-Functionalized Diketopyrrolopyrrole Chromophores. *The Journal of Organic Chemistry* **2011**, 76 (8), 2426-2432. https://doi.org/10.1021/jo2003117
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- **Pubblicato in:** The Journal of Organic Chemistry, vol. 76, n. 8, pp. 2426-2432 (2011)
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- **Editore:** American Chemical Society (ACS) · tipo: journal-article
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- **ISSN:** 0022-3263, 1520-6904
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- **Data di pubblicazione:** 2011-03-07
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- **Lingua:** en
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### Autori e affiliazioni
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- Hannah Bürckstümmer - University of Würzburg
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- Annike Weißenstein - University of Würzburg
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- David Bialas ([ORCID](https://orcid.org/0000-0001-5687-5904)) - University of Würzburg
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- Frank Würthner ([ORCID](https://orcid.org/0000-0001-7245-0471)) - University of Würzburg
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## Stato della verifica
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**Verificata (Crossref/OpenAlex)** - fonte dati: Crossref + OpenAlex
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## Dove trovarla
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- **DOI:** https://doi.org/10.1021/jo2003117
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- **PubMed:** https://pubmed.ncbi.nlm.nih.gov/21381701/
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- **OpenAlex:** https://openalex.org/W2321709959
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- **Accesso:** closed - il testo completo richiede un abbonamento dell'editore o l'acquisto
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## Abstract
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A series of six new 2,2'-bithiophene-functionalized diketopyrrolopyrrole (DPP) dyes 7a-f bearing different electron-donating and electron-withdrawing substituents at the terminal thiophene units was synthesized by palladium-catalyzed cross-coupling reactions. The to date unknown diiodinated DPP 2 and the corresponding boronic ester derivative 3 could be prepared in high yields, and these are shown to be versatile building blocks for the synthesis of DPP-based molecular materials by Negishi, Stille, and Suzuki coupling. The influence of the peripheral substituents on the optical and electrochemical properties of the present series of DPP dyes 7a-f were investigated by UV/vis and steady-state fluorescence spectroscopy and cyclic voltammetry, revealing an appreciable effect on the electronic nature of these dyes. The diamino-substituted DPP derivative 7e exhibits a strong absorption band reaching in the near-infrared (NIR) region, which is a highly desirable feature for application in organic photovoltaics.
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*(Fonte: Europe PMC. Non è il testo integrale dell'articolo.)*
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## Argomenti e parole chiave
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- **Argomenti (OpenAlex):** Organic Electronics and Photovoltaics (Electrical and Electronic Engineering); Synthesis and Properties of Aromatic Compounds (Organic Chemistry); Organic Light-Emitting Diodes Research (Electrical and Electronic Engineering)
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- **Parole chiave:** diketopyrrolopyrrole, bithiophene, palladium-catalyzed cross-coupling, boronic esters, peripheral substituent effects, near-infrared absorption, fluorescence, electrochemical properties, redox properties, organic solar cells
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- **Concetti:** Stille reaction, Chemistry, Thiophene, Negishi coupling, Cyclic voltammetry, Chromophore, Photochemistry, Suzuki reaction, Organic solar cell, Absorption spectroscopy
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## Contenuto in sintesi
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Il testo completo non è ad accesso aperto e non è stato consultato: sono disponibili solo i metadati e l'abstract riportati sopra. Per approfondire, aprire la fonte dal DOI (o tramite biblioteca/abbonamento).
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## Come è citata nella tesi
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- **Sez. 1.1.2 Struttura e reattività** (`tesi.md` r. 363): Un' ulteriore alternativa sintetica si basa sulla litiazione in posizione C5. Al pari di altri sistemi tiofenici, i DPP 29, 30 e 31 (Figura 21) reagiscono prontamente con LDA, aprendo la strada a diverse funzionalizzazioni (Figura 29). Come è possibile osservare nello schema, la reazione dell'intermedio litiato con formammidi (es. N-formilpiperidina o DMF) genera la dialdeide 43[30]. 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 44[31] e lo stannano 45[32]. Entrambi questi intermedi risultano di grande utilità per successivi step di cross coupling. Infine, è possibile isolare con buone rese il composto di-iodurato 46[31] effettuando il quenching della reazione con iodio molecolare.
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## Bibliografia della fonte
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La fonte cita 44 riferimenti (mostrati i primi 40; elenco completo: https://api.crossref.org/works/10.1021/jo2003117):
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- dWallquist, O.InHigh-Performance Pigments;Smith, H. M., Ed.Wiley-VCH:Weinheim, 2002, 159−184.
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- Fukuda M. Dyes Pigm. 2002 53 67 https://doi.org/10.1016/S0143-7208(02)00002-5
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- Fukuda M. Dyes Pigm. 2004 63 115 https://doi.org/10.1016/j.dyepig.2004.02.002
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- Langhals H. Angew. Chem., Int. Ed. Engl. 1989 28 478 https://doi.org/10.1002/anie.198904781
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- Cao D. Macromolecules 2006 39 8347 https://doi.org/10.1021/ma0615349
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- Qiao Z. Synth. Met. 2010 160 1544 https://doi.org/10.1016/j.synthmet.2010.05.019
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- Wienk M. M. Adv. Mater. 2008 20 2556 https://doi.org/10.1002/adma.200800456
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- Walker B. Adv. Funct. Mater. 2009 19 3063 https://doi.org/10.1002/adfm.200900832
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- Huo L. Macromolecules 2009 42 6564 https://doi.org/10.1021/ma9012972
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- Bijleveld J. C. Adv. Mater. 2010 22 E242 https://doi.org/10.1002/adma.201001449
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- Düggeli, M.; Zaher Eteish, M.; Hayoz, P.; Aebischer, O. F.; Fonronda Turon, M.; Fontana, M.; Lanz, M.; Turbiez, M. G. R.; Schmidhalter, B.; Flores, J.C.(BASF SE). WO2010049321, 2010.
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- ChemInform Abstract: Synthesis of Conjugated Polymer by the Stille Coupling Reaction. (1993) - https://doi.org/10.1002/chin.199318081 - citato 0 volte
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## Metriche
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- Citata **183** volte (OpenAlex); riferimenti nella fonte: 39
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- Citazioni per anno: 2026: 3, 2025: 4, 2024: 6, 2023: 3, 2022: 4, 2021: 13
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[Torna alla bibliografia della tesi](../tesi.md#ref-31) · Generata dal catalogo `bibliografia.json` e da Crossref, OpenAlex, Europe PMC.
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