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

Hao Pang, Peter Skabara, Sergey Gordeyev, Joseph J. W. McDouall, Simon J. Coles, Michael B. Hursthouse

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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 PEDSTthe 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).
Original languageUndefined/Unknown
Pages (from-to)301-307
Number of pages7
JournalChemistry of Materials
Volume19
Issue number2
DOIs
Publication statusPublished - 23 Jan 2007

Keywords

  • selenium
  • PEDOT
  • selenium analogue

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