Poly(3,4-ethylenediselena)thiophene - the selenium equivalent of PEDOT

Pang, Hao, Skabara, Peter J., Gordeyev, Sergey, McDouall, Joseph J.W., Coles, Simon J. and Hursthouse, Michael B. (2007) Poly(3,4-ethylenediselena)thiophene - the selenium equivalent of PEDOT. Chemistry of Materials, 19 (2), 301-307. (doi:10.1021/cm062242p).

Abstract

The first synthesis of the selenium analogue of EDOT, together with its electrochemical polymerization and redox and electronic properties of the resulting polymer, poly(3,4-ethylenediselena)thiophene (PEDST), is reported. The HOMO and LUMO values for the polymer (calculated from cyclic voltammetry experiments) are -4.8 and -3.3 eV, respectively, whereas the experimental band gap is 1.55 eV. Within the related series of polymersPEDOT, PEDTT, and PEDST the selenium analogue has a significantly lower LUMO value than the oxygen or sulfur derivatives (by ca. 0.55 eV). Quantum chemical calculations on trimers ((EDXT)(3), where X = O, S, or Se) show that the most planar conformation within the conjugated chain is achieved by EDOT systems. However, the calculated energy of a fixed planar conformation for PEDST is 13.9 kJ mol(-1) lower than the corresponding unconstrained conformer, indicating that a planar structure is preferred; this data corroborates the lower experimental band gap observed for PEDST (1.55 eV) compared to PEDTT (2.19 eV).

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Contributors

Author: Simon J. Coles

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