davideandClaude Sonnet 5.5
60aaca3418
Una scheda per fonte in fonti/ (metadati verificati con Crossref/OpenAlex/ Europe PMC, DOI e link, abstract, riassunto del contenuto per le fonti ad accesso aperto lette, citazioni nella tesi, bibliografia della fonte). bibliografia.json: campo fonte per ogni voce; CLAUDE.md aggiornato. Co-Authored-By: Claude Sonnet 5.5 <noreply@anthropic.com>
142 lines
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142 lines
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Markdown
---
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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): 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]. 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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- **Sez. 1.1.2 Struttura e reattività** (`tesi.md` r. 363): 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]. 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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- 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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- Novel Diketopyrrolopyrrole-Based π-Conjugated Molecules Synthesized Via One-Pot Direct Arylation Reaction (2019) - https://doi.org/10.3390/molecules24091760 - citato 14 volte
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- Preparation of π-conjugated polymers consisting of 2-decylbenzimidazole and thiophene units and chemical properties of the polymers (2002) - https://doi.org/10.1016/s0032-3861(01)00681-4 - citato 36 volte
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- Donor–acceptor molecules containing thiophene chromophore: synthesis, spectroscopic study and electrogenerated chemiluminescence (2006) - https://doi.org/10.1016/j.tetlet.2006.04.154 - citato 16 volte
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- Influence of thiophene spacer on conjugated polymer for organic photovoltaics (2016) - https://doi.org/10.1109/pvsc.2016.7749900 - citato 0 volte
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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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