Issue 41, 2021

Design, synthesis and characterization of fused bithiazole- and dithiophene-based low bandgap thienylenevinylene copolymers

Abstract

The structural rigidity of fused units in the polymer backbone, in addition to the resulting stabilizing effect of the quinoidal structure, and tunable electronic properties have played a key role in promoting highly-ordered π-stacking moieties, exhibiting promising charge carrier mobilities. The electron-deficient thiazole moiety shows high planarity and effective π–π stacking, which leads to the reduction in the energy levels of the highest occupied and lowest unoccupied molecular orbitals (HOMO/LUMO), and ideally enhances the electron charge mobility. Four heterocycle-based monomers BTzS, BTzSe, DTS, and DTG based on fused bithiazole and dithiophene units incorporated with sulfur, selenium, silicon, and germanium as the bridging atoms were synthesized and characterized. The monomers were copolymerized with the electron-rich alkylated thienylenevinylene (TV) unit to afford copolymers P1–P4. The thermal, optical, and electrochemical properties and crystallinity of the copolymers were thoroughly investigated. Extensive OFET device optimization using different solvents and annealing temperatures resulted in the best charge mobility of 0.09 cm2 V−1 s−1 for the electron-deficient bithiazole BTzS copolymer P1 and 0.36 cm2 V−1 s−1 for the DTS copolymer P3.

Graphical abstract: Design, synthesis and characterization of fused bithiazole- and dithiophene-based low bandgap thienylenevinylene copolymers

Supplementary files

Article information

Article type
Paper
Submitted
09 Jun 2021
Accepted
15 Sep 2021
First published
30 Sep 2021

Polym. Chem., 2021,12, 5942-5951

Author version available

Design, synthesis and characterization of fused bithiazole- and dithiophene-based low bandgap thienylenevinylene copolymers

D. Patra, M. Comí, X. Zhang, G. P. Kini, M. Udayakantha, A. J. Kalin, S. Banerjee, L. Fang, X. Guo and M. Al-Hashimi, Polym. Chem., 2021, 12, 5942 DOI: 10.1039/D1PY00773D

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