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

Poly(3,4-ethylenediselena)thiophene - the selenium equivalent of PEDOT
Poly(3,4-ethylenediselena)thiophene - the selenium equivalent of PEDOT
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).
field-effect transistors, solid-state synthesis, electrochromic devices, 2, 5-dibromothiophene, polythiophene, derivatives, copolymers, efficiency, chemistry, polymers
0897-4756
301-307
Pang, Hao
438515e5-79fd-48c5-9b8d-ea22ddeb47c0
Skabara, Peter J.
7138e414-7d50-41c7-933e-0bccad2fa4cd
Gordeyev, Sergey
358486ae-2e98-47ea-ace0-840aafd8737e
McDouall, Joseph J.W.
4ca54dfa-6b19-41d4-b531-a5cf701fdd68
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Pang, Hao
438515e5-79fd-48c5-9b8d-ea22ddeb47c0
Skabara, Peter J.
7138e414-7d50-41c7-933e-0bccad2fa4cd
Gordeyev, Sergey
358486ae-2e98-47ea-ace0-840aafd8737e
McDouall, Joseph J.W.
4ca54dfa-6b19-41d4-b531-a5cf701fdd68
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da

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).

Record type: Article

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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More information

Published date: 2007
Keywords: field-effect transistors, solid-state synthesis, electrochromic devices, 2, 5-dibromothiophene, polythiophene, derivatives, copolymers, efficiency, chemistry, polymers

Identifiers

Local EPrints ID: 44595
URI: http://eprints.soton.ac.uk/id/eprint/44595
ISSN: 0897-4756
PURE UUID: aca2ca76-b690-4a3c-891f-bd3fb8aee8f5
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 06 Mar 2007
Last modified: 16 Mar 2024 03:05

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Contributors

Author: Hao Pang
Author: Peter J. Skabara
Author: Sergey Gordeyev
Author: Joseph J.W. McDouall
Author: Simon J. Coles ORCID iD

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