Pang, H., Skabara, P.J., Crouch, D.J., Duffy, W., Heeney, M., McCulloch, I., Coles, S.J., Horton, P.N. and Hursthouse, M.B. (2007) Structural and electronic effects of 1,3,4-thiadiazole units incorporated into polythiophene chains. Macromolecules, 40 (18), 6585-6593. (doi:10.1021/ma071242n).
Abstract
A series of conjugated triaryl compounds have been synthesized, consisting of thiophene or selenophene peripheral units and a central 1,3,4-thiadiazole (TDA) heterocycle. X-ray crystallographic studies on four of the materials reveal that the molecules are planar in the solid state and feature an array of intramolecular (heteroatomic) and intermolecular (heteroatomic and -) noncovalent close contacts. Electrochemical oxidative polymerization affords insoluble polymers for EDOT-TDA-EDOT and EDTT-TDA-EDTT. The band gaps of the polymers have been deduced by cyclic voltammetry and electronic absorption spectroscopy and were found to be 1.8-1.9 eV. Both polymers show good stability toward n-doping and the EDTT analogue is more readily reduced than the EDOT-containing system. The enhanced stability toward n-doping, compared with the homopolymers PEDTT and PEDOT, is attributed to the presence of the electron deficient thiadiazole unit. The LUMO of poly(EDTT-TDA-EDTT) is 0.3 eV lower than that of poly(EDOT-TDA-EDOT), demonstrating that the substituent effect of the chalcogen atom is an important contributor to the electronic properties of the polymers.
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