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.