Experimental and theoretical studies into the structural perturbations between neutral, oxidised and reduced forms of 1,4-dithiinoquinoxaline derivatives

P.J. Skabara, R. Berridge, K. Prescott, L.M. Goldenberg, E. Ortí, R. Viruela, R. Pou-Amerigo, A.S. Batsanov, J.A.K. Howard, S.J. Coles, M.B. Hursthouse

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The syntheses and electrochemistry of thieno[3',4'∶5,6][1,4]dithiino[2,3-b]quinoxaline (9), 2,3-bis(methylsulfanyl)[1,4]dithiino[2,3-b]quinoxaline (16) and 2,3-ethylenedisulfanyl[1,4]dithiino[2,3-b]quinoxaline (17) are reported, together with the X-ray crystal structures of 9, 16 and the charge-transfer complex 9.TCNQ. In the thieno derivative 9, the molecular structure undergoes a significant change from a boat conformer to a planar system, upon oxidation with TCNQ. Theoretical calculations show that oxidation leads to planarisation of the molecular structure due to the aromatisation of the dithiine moiety. The study of the oxidised/reduced species helps to rationalise the electrochemical behaviour observed experimentally.
LanguageEnglish
Pages2448-2457
Number of pages9
JournalJournal of Materials Chemistry
Volume10
Issue number11
DOIs
Publication statusPublished - 2000

Fingerprint

Quinoxalines
Molecular structure
Derivatives
Aromatization
Oxidation
Boats
Electrochemistry
Charge transfer
Crystal structure
X rays
tetracyanoquinodimethane

Keywords

  • charge-transfer complex
  • TCNQ
  • dithiinoquinoxaline derivative

Cite this

Skabara, P.J. ; Berridge, R. ; Prescott, K. ; Goldenberg, L.M. ; Ortí, E. ; Viruela, R. ; Pou-Amerigo, R. ; Batsanov, A.S. ; Howard, J.A.K. ; Coles, S.J. ; Hursthouse, M.B. / Experimental and theoretical studies into the structural perturbations between neutral, oxidised and reduced forms of 1,4-dithiinoquinoxaline derivatives. In: Journal of Materials Chemistry. 2000 ; Vol. 10, No. 11. pp. 2448-2457.
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Skabara, PJ, Berridge, R, Prescott, K, Goldenberg, LM, Ortí, E, Viruela, R, Pou-Amerigo, R, Batsanov, AS, Howard, JAK, Coles, SJ & Hursthouse, MB 2000, 'Experimental and theoretical studies into the structural perturbations between neutral, oxidised and reduced forms of 1,4-dithiinoquinoxaline derivatives' Journal of Materials Chemistry, vol. 10, no. 11, pp. 2448-2457. https://doi.org/10.1039/b003910l

Experimental and theoretical studies into the structural perturbations between neutral, oxidised and reduced forms of 1,4-dithiinoquinoxaline derivatives. / Skabara, P.J.; Berridge, R.; Prescott, K.; Goldenberg, L.M.; Ortí, E.; Viruela, R.; Pou-Amerigo, R.; Batsanov, A.S.; Howard, J.A.K.; Coles, S.J.; Hursthouse, M.B.

In: Journal of Materials Chemistry, Vol. 10, No. 11, 2000, p. 2448-2457.

Research output: Contribution to journalArticle

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T1 - Experimental and theoretical studies into the structural perturbations between neutral, oxidised and reduced forms of 1,4-dithiinoquinoxaline derivatives

AU - Skabara, P.J.

AU - Berridge, R.

AU - Prescott, K.

AU - Goldenberg, L.M.

AU - Ortí, E.

AU - Viruela, R.

AU - Pou-Amerigo, R.

AU - Batsanov, A.S.

AU - Howard, J.A.K.

AU - Coles, S.J.

AU - Hursthouse, M.B.

PY - 2000

Y1 - 2000

N2 - The syntheses and electrochemistry of thieno[3',4'∶5,6][1,4]dithiino[2,3-b]quinoxaline (9), 2,3-bis(methylsulfanyl)[1,4]dithiino[2,3-b]quinoxaline (16) and 2,3-ethylenedisulfanyl[1,4]dithiino[2,3-b]quinoxaline (17) are reported, together with the X-ray crystal structures of 9, 16 and the charge-transfer complex 9.TCNQ. In the thieno derivative 9, the molecular structure undergoes a significant change from a boat conformer to a planar system, upon oxidation with TCNQ. Theoretical calculations show that oxidation leads to planarisation of the molecular structure due to the aromatisation of the dithiine moiety. The study of the oxidised/reduced species helps to rationalise the electrochemical behaviour observed experimentally.

AB - The syntheses and electrochemistry of thieno[3',4'∶5,6][1,4]dithiino[2,3-b]quinoxaline (9), 2,3-bis(methylsulfanyl)[1,4]dithiino[2,3-b]quinoxaline (16) and 2,3-ethylenedisulfanyl[1,4]dithiino[2,3-b]quinoxaline (17) are reported, together with the X-ray crystal structures of 9, 16 and the charge-transfer complex 9.TCNQ. In the thieno derivative 9, the molecular structure undergoes a significant change from a boat conformer to a planar system, upon oxidation with TCNQ. Theoretical calculations show that oxidation leads to planarisation of the molecular structure due to the aromatisation of the dithiine moiety. The study of the oxidised/reduced species helps to rationalise the electrochemical behaviour observed experimentally.

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