davideandClaude Sonnet 5.5
0f495b198e
- Sposta tesi.md, immagini, cataloghi e schede fonti in raw/ (immutabile); rimuove CHANGELOG, tesi.pdf e tesi.docx
- Riscrive CLAUDE.md: dominio, regole sui dati, ingest per capitolo, tesi_loc
- Aggiunge scripts/gen_figures.py e le 78 note in wiki/figures/ da raw/immagini.json
- Aggiunge index.md, log.md, wiki/tesi.md (mappa) e le cartelle wiki/{compounds,techniques,concepts,analyses}
Co-Authored-By: Claude Sonnet 5.5 <noreply@anthropic.com>
145 lines
11 KiB
Markdown
145 lines
11 KiB
Markdown
---
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id: 29
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anchor: ref-29
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stato: verificata
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doi: 10.1039/c2ta01318e
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url: https://doi.org/10.1039/c2ta01318e
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anno: 2013
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rivista: "Journal of Materials Chemistry A"
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volume: "1"
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pagine: "2795"
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editore: "Royal Society of Chemistry (RSC)"
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tipo: journal-article
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autori: ["Shiyong Liu", "Minmin Shi", "Jia-Chi Huang", "Zhengneng Jin", "Xiaolian Hu", "Junying Pan", "Hanying Li", "Alex K.‐Y. Jen", "Hongzheng Chen"]
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accesso: closed
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licenza: null
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pmcid: null
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citata_da: 131
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argomenti: ["Catalytic C–H Functionalization Methods", "Catalytic Cross-Coupling Reactions", "Synthesis and Properties of Aromatic Compounds"]
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parole_chiave: ["diketopyrrolopyrrole", "C–H activation", "palladium catalysis", "direct arylation", "conjugated molecules", "phosphine-free catalysis", "atom economy", "optical properties", "electrochemical properties"]
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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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# [29] Liu (2013) - C–H activation: making diketopyrrolopyrrole derivatives easily accessible
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## Come è scritta nella tesi
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Liu, S.-Y. *et al.* C–H activation: making diketopyrrolopyrrole derivatives easily accessible. *J. Mater. Chem. A* **1**, 2795 (2013).
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## Scheda bibliografica
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**Citazione completa:** Liu, S. Y.; Shi, M. M.; Huang, J. C.; Jin, Z. N.; Hu, X. L.; Pan, J. Y.; Li, H. Y.; Jen, A. K. Y.; Chen, H. Z. C–H activation: making diketopyrrolopyrrole derivatives easily accessible. *Journal of Materials Chemistry A* **2013**, 1 (8), 2795. https://doi.org/10.1039/c2ta01318e
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- **Pubblicato in:** Journal of Materials Chemistry A, vol. 1, n. 8, pp. 2795 (2013)
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- **Editore:** Royal Society of Chemistry (RSC) · tipo: journal-article
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- **ISSN:** 2050-7488, 2050-7496
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- **Data di pubblicazione:** 2012-12-21
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- **Lingua:** en
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### Autori e affiliazioni
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- Shiyong Liu ([ORCID](https://orcid.org/0000-0002-3569-3826)) - State Key Laboratory of Silicon Materials; Taizhou University; Zhejiang University
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- Minmin Shi ([ORCID](https://orcid.org/0000-0001-7692-2624)) - State Key Laboratory of Silicon Materials; Zhejiang University
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- Jia-Chi Huang - State Key Laboratory of Silicon Materials; Zhejiang University
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- Zhengneng Jin - State Key Laboratory of Silicon Materials; Taizhou University; Zhejiang University
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- Xiaolian Hu - State Key Laboratory of Silicon Materials; Zhejiang University
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- Junying Pan - State Key Laboratory of Silicon Materials; Zhejiang University
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- Hanying Li ([ORCID](https://orcid.org/0000-0002-5841-6805)) - State Key Laboratory of Silicon Materials; Zhejiang University
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- Alex K.‐Y. Jen ([ORCID](https://orcid.org/0000-0002-9219-7749)) - University of Washington; State Key Laboratory of Silicon Materials; Zhejiang University
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- Hongzheng Chen ([ORCID](https://orcid.org/0000-0002-5922-9550)) - State Key Laboratory of Silicon Materials; Zhejiang University
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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/10.1039/c2ta01318e
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- **OpenAlex:** https://openalex.org/W2052052579
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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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Diketopyrrolopyrrole (DPP) derivatives are an important class of high-performance pigment used in inks, paints, plastics, and organic electronics. Until now, DPP derivatives containing sophisticated aryl units at the DPP core have usually been obtained via Suzuki, Stille, or Negishi cross-coupling reactions, which require organometallic precursors. In this work, a series of DPP-based π-conjugated molecules bearing diverse aryl substituents on the thiophene- or benzene-DPPs were facilely synthesized in moderate to excellent yields through the Pd-catalyzed direct arylation of C–H bonds. The synthetic procedures feature advantages over traditional C–C cross-coupling reactions such as: (1) avoidance of the use of organometallic reagents in the starting materials leading to simpler byproducts and higher atom economy, (2) fewer synthetic steps, (3) higher yields, (4) better compatibility with chemically sensitive functional groups, and (5) simpler catalytic systems free of phosphine ligands. These advantages make the present protocol an ideal and versatile strategy for the synthesis of DPP derivatives, especially for structurally complicated DPPs that may possess chemically sensitive functionalities. The optical and electrochemical properties of the synthesized DPPs (17 compounds) were systematically investigated using UV-vis spectroscopy, steady-state fluorescence spectroscopy, and cyclic voltammetry (CV).
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*(Fonte: OpenAlex. Non è il testo integrale dell'articolo.)*
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## Argomenti e parole chiave
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- **Argomenti (OpenAlex):** Catalytic C–H Functionalization Methods (Organic Chemistry); Catalytic Cross-Coupling Reactions (Organic Chemistry); Synthesis and Properties of Aromatic Compounds (Organic Chemistry)
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- **Parole chiave:** diketopyrrolopyrrole, C–H activation, palladium catalysis, direct arylation, conjugated molecules, phosphine-free catalysis, atom economy, optical properties, electrochemical properties
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- **Concetti:** Stille reaction, Negishi coupling, Aryl, Combinatorial chemistry, Chemistry, Thiophene, Conjugated system, Catalysis, Cyclic voltammetry, Molecule
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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. 339): In due studi indipendenti, i gruppi di ricerca guidati da Marder e Chen[29] hanno esplorato con successo le potenzialità di un particolare precursore DPP (29), impiegandolo come molecola di partenza per reazioni di arilazione diretta condotte in presenza di diversi bromoareni (Figura 25).
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## Bibliografia della fonte
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La fonte cita 53 riferimenti (mostrati i primi 40; elenco completo: https://api.crossref.org/works/10.1039/c2ta01318e):
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- Farnum Tetrahedron Lett. 1974 29 2549 https://doi.org/10.1016/S0040-4039(01)93202-2
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- Wallquist Macromol. Symp. 2002 187 617 https://doi.org/10.1002/1521-3900(200209)187:1<617::AID-MASY617>3.0.CO;2-5
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- Qu Chem. Commun. 2012 48 3039 https://doi.org/10.1039/c2cc17886a
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- Biniek J. Mater. Chem. 2012 22 14803 https://doi.org/10.1039/c2jm31943h
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- Beaujuge J. Am. Chem. Soc. 2011 133 20009 https://doi.org/10.1021/ja2073643
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- Huo Macromolecules 2009 42 6564 https://doi.org/10.1021/ma9012972
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- Lin Chem. Commun. 2012 48 4773 https://doi.org/10.1039/c2cc31511d
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- Chen J. Phys. Chem. C 2011 115 11282 https://doi.org/10.1021/jp201104s
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- Hu J. Mater. Chem. 2012 22 15710 https://doi.org/10.1039/c2jm31700a
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- Hu Polymer 2011 52 2559 https://doi.org/10.1016/j.polymer.2011.03.057
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- Cheng Chem. Mater. 2011 23 2361 https://doi.org/10.1021/cm200041v
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- Chen Adv. Mater. 2012 24 4618 https://doi.org/10.1002/adma.201201318
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- Li Org. Electron. 2012 13 2450 https://doi.org/10.1016/j.orgel.2012.07.011
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- Yi Chem. Mater. 2012 24 4350 https://doi.org/10.1021/cm302341m
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- Lee Macromol. Rapid Commun. 2012 33 140 https://doi.org/10.1002/marc.201100643
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- Walker Adv. Funct. Mater. 2009 19 3063 https://doi.org/10.1002/adfm.200900832
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- Chen J. Mater. Chem. A 2013 1 105 https://doi.org/10.1039/C2TA00148A
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- Kylberg Energy Environ. Sci. 2011 4 3617 https://doi.org/10.1039/c1ee01544c
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- Lee Adv. Mater. 2011 23 5359 https://doi.org/10.1002/adma.201103177
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- Tamayo Appl. Phys. Lett. 2009 94 103301 https://doi.org/10.1063/1.3086897
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- Sonar J. Mater. Chem. 2010 20 3626 https://doi.org/10.1039/b924404b
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- Karsten Macromol. Rapid Commun. 2010 31 1554 https://doi.org/10.1002/marc.201000133
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- Lin Chem. Commun. 2012 48 4773 https://doi.org/10.1039/c2cc31511d
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- Walker Chem. Mater. 2011 23 470 https://doi.org/10.1021/cm102189g
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- Suraru Chem. Commun. 2011 47 1767 https://doi.org/10.1039/C0CC04395H
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- Qu Chem. Commun. 2012 48 6972 https://doi.org/10.1039/c2cc31998e
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- Qu Org. Lett. 2010 12 3320 https://doi.org/10.1021/ol101081m
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- Yamagata Tetrahedron Lett. 2010 51 1596 https://doi.org/10.1016/j.tetlet.2010.01.069
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- Deng J. Org. Chem. 2011 76 9294 https://doi.org/10.1021/jo201487m
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- Burckstummer J. Org. Chem. 2011 76 2426 https://doi.org/10.1021/jo2003117
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- Lafrance J. Am. Chem. Soc. 2006 128 8754 https://doi.org/10.1021/ja062509l
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- Lafrance J. Am. Chem. Soc. 2006 128 16496 https://doi.org/10.1021/ja067144j
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- García-Cuadrado J. Am. Chem. Soc. 2006 128 1066 https://doi.org/10.1021/ja056165v
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- Gorelsky J. Org. Chem. 2012 77 658 https://doi.org/10.1021/jo202342q
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- Liégault J. Org. Chem. 2009 74 1826 https://doi.org/10.1021/jo8026565
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- Gorelsky J. Am. Chem. Soc. 2008 130 10848 https://doi.org/10.1021/ja802533u
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- Lapointe Chem. Lett. 2010 39 1118 https://doi.org/10.1246/cl.2010.1118
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- Potavathri J. Am. Chem. Soc. 2010 132 14676 https://doi.org/10.1021/ja107159b
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- Campeau J. Am. Chem. Soc. 2008 130 3276 https://doi.org/10.1021/ja7107068
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- Caron Org. Lett. 2008 10 4533 https://doi.org/10.1021/ol801839w
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## Lavori correlati (OpenAlex)
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- Synthesis of Mixed Thiophene/Furan Oligomers by Stille Coupling (1998) - https://doi.org/10.1021/jo981159l - citato 66 volte
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- Halogenated 2‘-Chlorobithiazoles via Pd-Catalyzed Cross-Coupling Reactions (2006) - https://doi.org/10.1021/jo0601009 - citato 58 volte
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- Introduction of Aromatic and Heteroaromatic Groups in the 2‐ and 8‐Positions of the Tröger’s Base Core by Suzuki, Stille and Negishi Cross‐Coupling Reactions – A Comparative Study (2005) - https://doi.org/10.1002/ejoc.200500213 - citato 40 volte
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- Comparative Study on the Reactivity of 6‐Haloimidazo[1,2‐a]pyridine Derivatives towards Negishi‐ and Stille‐Coupling Reactions (2003) - https://doi.org/10.1002/hlca.200390290 - citato 20 volte
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- Comparative Study on the Reactivity of 6‐Haloimidazo[1,2‐a]pyridine Derivatives Towards Negishi‐ and Stille‐Coupling Reactions. (2004) - https://doi.org/10.1002/chin.200410143 - citato 1 volte
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- Preparation of 5-Heteroaryl Substituted 1-(4-Fluorophenyl)-1H-indoles via Palladium-Catalyzed Negishi and Stille Cross-Coupling Reactions (2002) - https://doi.org/10.1055/s-2002-33338 - citato 5 volte
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- Preparation of 5‐Heteroaryl Substituted 1‐(4‐Fluorophenyl)‐1H‐indoles via Palladium‐Catalyzed Negishi and Stille Cross‐Coupling Reactions. (2002) - https://doi.org/10.1002/chin.200250087 - citato 1 volte
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- Research Progress of Pd Catalyzed Cross-coupling Reactions Utilized in Solid Phase Organic Synthesis (2011) - citato 0 volte
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## Metriche
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- Citata **131** volte (OpenAlex); riferimenti nella fonte: 54
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- Citazioni per anno: 2026: 3, 2025: 3, 2024: 7, 2023: 2, 2022: 9, 2021: 6
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[Torna alla bibliografia della tesi](../tesi.md#ref-29) · Generata dal catalogo `bibliografia.json` e da Crossref, OpenAlex, Europe PMC.
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