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

Skabara, P.J. and Berridge, R. and Prescott, K. and Goldenberg, L.M. and Ortí, E. and Viruela, R. and Pou-Amerigo, R. and Batsanov, A.S. and Howard, J.A.K. and Coles, S.J. and 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). pp. 2448-2457. ISSN 0959-9428

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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.