CC BY-NC-ND 4.0 · Organic Materials 2023; 5(01): 35-47
DOI: 10.1055/a-1972-5895
Original Article

Broadly Applicable Synthesis of Heteroarylated Dithieno[3,2-b:2′,3′-d]pyrroles for Advanced Organic Materials – Part 1: Conducting Electropolymers

Christoph Lorenz
a   Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany
,
Astrid Vogt
a   Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany
,
b   Dpto. de Química – Facultad de Ciencia y Tecnología, Universidad de la Rioja, Madre de Dios, 53, 26006 Logroño-La Rioja, España
,
a   Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany
,
a   Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany
› Institutsangaben


Abstract

Herein, a novel and versatile method for the synthesis of N-heteroarylated dithieno[3,2-b:2,3′-d]pyrroles (DTPs) is reported. By microwave-assisted Cu-catalyzed coupling of parent H-DTP 1 with 5- and 6-membered heteroaromatic halides, a variety of novel N-functionalized DTPs were obtained. Supported by quantum chemical calculations and X-ray structure analysis, structural and optoelectronic properties of the π-conjugated systems were investigated and led to valuable structure–property relationships. Selected derivatives were electropolymerized to corresponding conducting DTP polymers.



Publikationsverlauf

Eingereicht: 12. August 2022

Angenommen nach Revision: 27. Oktober 2022

Accepted Manuscript online:
04. November 2022

Artikel online veröffentlicht:
27. Januar 2023

© 2023. The authors. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany