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Linearly extended tetrathiafulvalene analogues with fused thiophene units as pi-conjugated spacers

Leriche, P. and Raimundo, J.M. and Turbiez, M. and Monroche, V. and Allain, M. and Sauvage, F.X. and Roncali, J. and Frere, P. and Skabara, P.J. (2003) Linearly extended tetrathiafulvalene analogues with fused thiophene units as pi-conjugated spacers. Journal of Materials Chemistry, 13 (6). pp. 1324-1332. ISSN 0959-9428

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A new series of linearly extended tetrathiafulvalene analogues with thienothiophene and dithienothiophene pi-conjugating spacers has been synthesized. Electronic absorption spectra present a vibronic fine structure typical for rigid conjugated systems. Investigation of the electrochemical behaviour of the new donors by cyclic voltammetry reveals the successive generation of stable radical cation and dication species. The crystallographic structure of a single crystal of a dication salt of TT-TTF(ClO4)(2) has been analysed by X-ray diffraction. The dication presents a syn conformation stabilised by S...S intramolecular interactions. The quinoid structure expected for the spacer for the +2 oxidation state is clearly revealed by the bond lengths.