davideandClaude Sonnet 5.5
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Co-Authored-By: Claude Sonnet 5.5 <noreply@anthropic.com>
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| 31 | ref-31 | verificata | 10.1021/jo2003117 | https://doi.org/10.1021/jo2003117 | 2011 | The Journal of Organic Chemistry | 76 | 2426-2432 | American Chemical Society (ACS) | journal-article |
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[31] Bürckstümmer (2011) - Synthesis and Characterization of Optical and Redox Properties of Bithiophene-Functionalized Diketopyrrolopyrrole Chromophores
Come è scritta nella tesi
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).
Scheda bibliografica
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
- Pubblicato in: The Journal of Organic Chemistry, vol. 76, n. 8, pp. 2426-2432 (2011)
- Editore: American Chemical Society (ACS) · tipo: journal-article
- ISSN: 0022-3263, 1520-6904
- Data di pubblicazione: 2011-03-07
- Lingua: en
Autori e affiliazioni
- Hannah Bürckstümmer - University of Würzburg
- Annike Weißenstein - University of Würzburg
- David Bialas (ORCID) - University of Würzburg
- Frank Würthner (ORCID) - University of Würzburg
Stato della verifica
Verificata (Crossref/OpenAlex) - fonte dati: Crossref + OpenAlex
Dove trovarla
- DOI: https://doi.org/10.1021/jo2003117
- PubMed: https://pubmed.ncbi.nlm.nih.gov/21381701/
- OpenAlex: https://openalex.org/W2321709959
- Accesso: closed - il testo completo richiede un abbonamento dell'editore o l'acquisto
Abstract
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.
(Fonte: Europe PMC. Non è il testo integrale dell'articolo.)
Argomenti e parole chiave
- 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)
- Parole chiave: diketopyrrolopyrrole, bithiophene, palladium-catalyzed cross-coupling, boronic esters, peripheral substituent effects, near-infrared absorption, fluorescence, electrochemical properties, redox properties, organic solar cells
- Concetti: Stille reaction, Chemistry, Thiophene, Negishi coupling, Cyclic voltammetry, Chromophore, Photochemistry, Suzuki reaction, Organic solar cell, Absorption spectroscopy
Contenuto in sintesi
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).
Come è citata nella tesi
- Sez. 1.1.2 Struttura e reattività (
tesi.mdr. 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. - Sez. 1.1.2 Struttura e reattività (
tesi.mdr. 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.
Bibliografia della fonte
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Metriche
- Citata 183 volte (OpenAlex); riferimenti nella fonte: 39
- Citazioni per anno: 2026: 3, 2025: 4, 2024: 6, 2023: 3, 2022: 4, 2021: 13
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