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., 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), 2448-2457. (doi: 10.1039/b003910l).

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Description/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.

Item Type: Article
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Keywords: charge-transfer complex, tcnq, dithiinoquinoxaline derivative charge-transfer salts, organic superconductors, crystal-structures, correlation-energy, reaction field, ab-initio, donors, molecules, complexes, chemistry
Subjects: Q Science
Q Science > QD Chemistry
Divisions: University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 19023
Date Deposited: 18 Jan 2006
Last Modified: 27 Mar 2014 18:08
URI: http://eprints.soton.ac.uk/id/eprint/19023

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