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

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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.
Original languageEnglish
Pages (from-to)2448-2457
Number of pages9
JournalJournal of Materials Chemistry
Volume10
Issue number11
DOIs
Publication statusPublished - 2000

Keywords

  • charge-transfer complex
  • TCNQ
  • dithiinoquinoxaline derivative

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    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. (2000). Experimental and theoretical studies into the structural perturbations between neutral, oxidised and reduced forms of 1,4-dithiinoquinoxaline derivatives. Journal of Materials Chemistry, 10(11), 2448-2457. https://doi.org/10.1039/b003910l