Experimental and theoretical studies into thestructural perturbations between neutral, oxidised and reduced forms of 1,4-dithiinoquinoxalinederivatives

Peter J. Skabara; Rory Berridge; Karen Prescott; Leonid M. Goldenberg; Enrique Ortí; Rafael Viruela; Rosendo Pou-Amérigo; Andrei S. Batsanov; Judith A. K. Howard; Simon J. Coles; Michael B. Hursthouse

doi:10.1039/B003910L

Peter J. Skabara,†*^a Rory Berridge,^a Karen Prescott,^a Leonid M. Goldenberg,‡^b Enrique Ortí,*^c Rafael Viruela,^c Rosendo Pou-Amérigo,^c Andrei S. Batsanov,^d Judith A. K. Howard,^d Simon J. Coles^e and Michael B. Hursthouse^e

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* Corresponding authors

^a Division of Chemistry, Sheffield Hallam University, Sheffield, UK
E-mail: P.J.Skabara@man.ac.uk

^b Institute of Problems of Chemical Physics, Russian Academy of Science, Chernogolovka, Russia1

^c Department of Physical Chemistry, University of Valencia, Valencia, Spain

^d Department of Chemistry, University of Durham, Durham, UK

^e Department of Chemistry, University of Southampton, Southampton, UK

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.

Journal of Materials Chemistry

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

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