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Broadly Applicable Synthesis of Arylated Dithieno[3,2-b:2',3'-d]pyrroles as Building Blocks for Organic Electronic Materials.

ABSTRACT: A novel and versatile method for the N-arylation of dithieno[3,2-b:2',3'-d]pyrrole (DTP) is presented. By Pd- or Cu-catalyzed coupling a variety of arenes and acenes were directly attached at the DTP-nitrogen yielding a variety of functionalized DTPs. Investigations on optical and redox properties led to valuable structure-property relationships, which were corroborated by quantum chemical calculations. Further functionalization and elongation of the conjugation of an acceptor-substituted DTP was elaborated to result in complex cruciform-type donor-acceptor oligomers, which were investigated and implemented in single material organic solar cells.

SUBMITTER: Vogt A

PROVIDER: S-EPMC8456814 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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Broadly Applicable Synthesis of Arylated Dithieno[3,2-b:2',3'-d]pyrroles as Building Blocks for Organic Electronic Materials.

Vogt Astrid A Schwer Fabian F Förtsch Sebastian S Lorenz Christoph C Mena-Osteritz Elena E Aubele Anna A Kraus Teresa T Bäuerle Peter P

Chemistry (Weinheim an der Bergstrasse, Germany) 20210729 48

A novel and versatile method for the N-arylation of dithieno[3,2-b:2',3'-d]pyrrole (DTP) is presented. By Pd- or Cu-catalyzed coupling a variety of arenes and acenes were directly attached at the DTP-nitrogen yielding a variety of functionalized DTPs. Investigations on optical and redox properties led to valuable structure-property relationships, which were corroborated by quantum chemical calculations. Further functionalization and elongation of the conjugation of an acceptor-substituted DTP wa ...[more]

PMID: 34152046

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