Issue 10, 2017

Novel vinylene-bridged donor–acceptor copolymers: synthesis, characterization, properties and effect of cyano substitution

Abstract

Two novel vinylene-bridged π-extended building blocks, (2E,2′E)-3,3′-(2,5-bis(octyloxy)-1,4-phenylene)bis(2-(5-bromothiophen-2-yl)acrylonitrile) (BOPACN) and 5,5′-((1E,1′E)-(2,5-bis(octyloxy)-1,4-phenylene)bis(ethene-1,2-diyl))bis(2-bromothiophene) (BOPA), were synthesized. They were further copolymerized with two diketopyrrolopyrrole (DPP) units possessing different alkyl side chains, and four donor–acceptor copolymers, namely PBOPACN-1, PBOPACN-2, PBOPA-1 and PBOPA-2, were synthesized. The optical, thermal, and electrochemical properties and field-effect properties of all copolymers were systematically investigated by theoretical calculations and experimental methods. Field-effect transistors based on these copolymers exhibited p-type charge transport characteristics in air. The performance implies that cyano substituents exert an important influence on semiconducting behaviours. Furthermore, 2D-GIXRD and theoretical calculations demonstrate that the presence of cyano substituents improves molecular planarity and generates highly-ordered molecular aggregates for PBOPACN-1 and PBOPACN-2.

Graphical abstract: Novel vinylene-bridged donor–acceptor copolymers: synthesis, characterization, properties and effect of cyano substitution

Supplementary files

Article information

Article type
Research Article
Submitted
25 Mai 2017
Accepted
17 Jul 2017
First published
18 Jul 2017

Mater. Chem. Front., 2017,1, 2103-2110

Novel vinylene-bridged donor–acceptor copolymers: synthesis, characterization, properties and effect of cyano substitution

C. Wei, J. Zou, W. Zhang, J. Huang, D. Gao, L. Wang, Y. Liao and G. Yu, Mater. Chem. Front., 2017, 1, 2103 DOI: 10.1039/C7QM00236J

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