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

Abby Casey; Yang Han; Zhuping Fei; Andrew J.P. White; Thomas D. Anthopoulos; Martin Heeney

doi:10.1039/c4tc02008a

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

Abby Casey, Yang Han, Zhuping Fei^*, Andrew J.P. White, Thomas D. Anthopoulos, Martin Heeney

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

94 Scopus citations

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.

Original language	English (US)
Pages (from-to)	265-275
Number of pages	11
Journal	JOURNAL OF MATERIALS CHEMISTRY C
Volume	3
Issue number	2
DOIs	https://doi.org/10.1039/c4tc02008a
State	Published - Jan 14 2015
Externally published	Yes

ASJC Scopus subject areas

General Chemistry
Materials Chemistry

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title = "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.",

author = "Abby Casey and Yang Han and Zhuping Fei and White, {Andrew J.P.} and Anthopoulos, {Thomas D.} and Martin Heeney",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2015.",

year = "2015",

month = jan,

day = "14",

doi = "10.1039/c4tc02008a",

language = "English (US)",

volume = "3",

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T1 - Cyano substituted benzothiadiazole

T2 - A novel acceptor inducing n-type behaviour in conjugated polymers

AU - Casey, Abby

AU - Han, Yang

AU - Fei, Zhuping

AU - White, Andrew J.P.

AU - Anthopoulos, Thomas D.

AU - Heeney, Martin

PY - 2015/1/14

Y1 - 2015/1/14

N2 - 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.

AB - 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.

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U2 - 10.1039/c4tc02008a

DO - 10.1039/c4tc02008a

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VL - 3

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JF - JOURNAL OF MATERIALS CHEMISTRY C

IS - 2

ER -

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

Abstract

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