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

Research output: Contribution to journalArticle

42 Citations (Scopus)

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).
LanguageUndefined/Unknown
Pages301-307
Number of pages7
JournalChemistry of Materials
Volume19
Issue number2
DOIs
Publication statusPublished - 23 Jan 2007

Keywords

  • selenium
  • PEDOT
  • selenium analogue

Cite this

Pang, H., Skabara, P., Gordeyev, S., McDouall, J. J. W., Coles, S. J., & Hursthouse, M. B. (2007). Poly(3,4-ethylenediselena)thiophene - the selenium equivalent of PEDOT. Chemistry of Materials, 19(2), 301-307. https://doi.org/10.1021/cm062242p
Pang, Hao ; Skabara, Peter ; Gordeyev, Sergey ; McDouall, Joseph J. W. ; Coles, Simon J. ; Hursthouse, Michael B. / Poly(3,4-ethylenediselena)thiophene - the selenium equivalent of PEDOT. In: Chemistry of Materials. 2007 ; Vol. 19, No. 2. pp. 301-307.
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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).",
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Pang, H, Skabara, P, Gordeyev, S, McDouall, JJW, Coles, SJ & Hursthouse, MB 2007, 'Poly(3,4-ethylenediselena)thiophene - the selenium equivalent of PEDOT' Chemistry of Materials, vol. 19, no. 2, pp. 301-307. https://doi.org/10.1021/cm062242p

Poly(3,4-ethylenediselena)thiophene - the selenium equivalent of PEDOT. / Pang, Hao; Skabara, Peter; Gordeyev, Sergey; McDouall, Joseph J. W.; Coles, Simon J.; Hursthouse, Michael B.

In: Chemistry of Materials, Vol. 19, No. 2, 23.01.2007, p. 301-307.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Poly(3,4-ethylenediselena)thiophene - the selenium equivalent of PEDOT

AU - Pang, Hao

AU - Skabara, Peter

AU - Gordeyev, Sergey

AU - McDouall, Joseph J. W.

AU - Coles, Simon J.

AU - Hursthouse, Michael B.

PY - 2007/1/23

Y1 - 2007/1/23

N2 - 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).

AB - 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).

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KW - PEDOT

KW - selenium analogue

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Pang H, Skabara P, Gordeyev S, McDouall JJW, Coles SJ, Hursthouse MB. Poly(3,4-ethylenediselena)thiophene - the selenium equivalent of PEDOT. Chemistry of Materials. 2007 Jan 23;19(2):301-307. https://doi.org/10.1021/cm062242p