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

Record type: Article

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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Citation

Skabara, P. J., Berridge, R., Prescott, K., Goldenberg, L. M., Orti, E., Viruela, R., Pou-Amerigo, R., Batsanov, A. S., Howard, J. A. K., 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. (doi:10.1039/b003910l).

More information

Published date: 2000
Keywords: charge-transfer complex, tcnq, dithiinoquinoxaline derivative charge-transfer salts, organic superconductors, crystal-structures, correlation-energy, reaction field, ab-initio, donors, molecules, complexes, chemistry

Identifiers

Local EPrints ID: 19023
URI: http://eprints.soton.ac.uk/id/eprint/19023
PURE UUID: 98dc1b0c-c89d-4f0a-aded-4983d73629c6

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Date deposited: 18 Jan 2006
Last modified: 17 Jul 2017 16:34

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Contributors

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

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