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Issue 11, 2000
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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.

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Article information


Submitted
16 May 2000
Accepted
21 Jul 2000
First published
27 Sep 2000

J. Mater. Chem., 2000,10, 2448-2457
Article type
Paper

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-Amérigo, A. S. Batsanov, J. A. K. Howard, S. J. Coles and M. B. Hursthouse, J. Mater. Chem., 2000, 10, 2448
DOI: 10.1039/B003910L

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