---
id: 31
anchor: ref-31
stato: verificata
doi: 10.1021/jo2003117
url: https://doi.org/10.1021/jo2003117
anno: 2011
rivista: "The Journal of Organic Chemistry"
volume: "76"
pagine: "2426-2432"
editore: "American Chemical Society (ACS)"
tipo: journal-article
autori: ["Hannah Bürckstümmer", "Annike Weißenstein", "David Bialas", "Frank Würthner"]
accesso: closed
licenza: null
pmcid: null
citata_da: 183
argomenti: ["Organic Electronics and Photovoltaics", "Synthesis and Properties of Aromatic Compounds", "Organic Light-Emitting Diodes Research"]
parole_chiave: ["diketopyrrolopyrrole", "bithiophene", "palladium-catalyzed cross-coupling", "boronic esters", "peripheral substituent effects", "near-infrared absorption", "fluorescence", "electrochemical properties", "redox properties", "organic solar cells"]
contenuto_letto: solo_abstract
tags: [fonte, bibliografia]
cited_in_sections: [1.1.2]
---

# [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](https://orcid.org/0000-0001-5687-5904)) - University of Würzburg
- Frank Würthner ([ORCID](https://orcid.org/0000-0001-7245-0471)) - 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.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.
- **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.

## 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

[Torna alla bibliografia della tesi](../tesi.md#ref-31) · Generata dal catalogo `bibliografia.json` e da Crossref, OpenAlex, Europe PMC.