Issue 2, 2015

Cyano substituted benzothiadiazole: a novel acceptor inducing n-type behaviour in conjugated polymers

Abstract

We report the synthesis of the novel acceptor, 4,7-di(thiophen-2-yl)-5,6-dicyano-2,1,3-benzothiadiazole (DTDCNBT) and compare its properties to those of the previously reported 4,7-di(thiophen-2-yl)-5,6-difluoro-2,1,3-benzothiadiazole (DTDFBT). Co-polymers of both monomers with the donor monomers indacenodithiophene (IDT) and dithienogermole (DTG) were prepared and investigated. The DTDCNBT unit was found to be a much stronger electron acceptor than DTDFBT. The electron affinity of the cyanated polymers was increased by up to ∼0.4 eV, resulting in red-shifted absorptions and reduced optical band gaps. In field effect transistors it was found that replacing the fluorine substituents of the polymers with cyano groups changed the charge transport from unipolar p-type to unipolar n-type.

Graphical abstract: Cyano substituted benzothiadiazole: a novel acceptor inducing n-type behaviour in conjugated polymers

Supplementary files

Article information

Article type
Paper
Submitted
08 Sep 2014
Accepted
17 Oct 2014
First published
21 Oct 2014
This article is Open Access
Creative Commons BY license

J. Mater. Chem. C, 2015,3, 265-275

Author version available

Cyano substituted benzothiadiazole: a novel acceptor inducing n-type behaviour in conjugated polymers

A. Casey, Y. Han, Z. Fei, A. J. P. White, T. D. Anthopoulos and M. Heeney, J. Mater. Chem. C, 2015, 3, 265 DOI: 10.1039/C4TC02008A

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