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New functionalized tetrathiafulvalenes: X-ray crystal structures and physico-chemical properties of TTF-C(O)NMe2 and TTF-C(O)-O-C4H9: a joint experimental and theoretical study

Batsanov, A.S. and Bryce, M.R. and Heaton, J.N. and Moore, A.J. and Skabara, P.J. and Howard, J.A.K. and Ortí, E. and Viruela, P.M. and Viruela, R. (1995) New functionalized tetrathiafulvalenes: X-ray crystal structures and physico-chemical properties of TTF-C(O)NMe2 and TTF-C(O)-O-C4H9: a joint experimental and theoretical study. Journal of Materials Chemistry, 5 (10). pp. 1689-1696. ISSN 0959-9428

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Abstract

The synthesis of the new mono- and di-functionalized tetrathiafulvalene (TTF) derivatives 4, 5 and 12-15 is reported. Compounds 4 and 5 have been studied in detail: their single crystal X-ray structures are reported and theoretical calculations at both semiempirical and ab initio levels have been performed. The TTF moiety in the crystal of 4 is folded, whereas in the crystal of 5 it is essentially planar. In the crystal structure of 4 the molecules related via an inversion centre form close dimers which pack in a severely distorted kappa-arrangement. Molecules of 5 assemble into uniform stacks with TTF moieties overlapping the side chains of adjacent molecules. Calculated geometries are in good agreement with the X-ray data, and the distortion from planarity in the crystal of 4 can be explained by nonbonding interactions between the amide substituent and the TTF rings of adjacent molecules. Evidence for intramolecular charge-transfer from the TTF ring to the electron-withdrawing amide and ester substituents of 4 and 5, respectively, is provided by UV-VIS spectroscopy in solution, analysis of the bond lengths in the crystal structure, and by theoretical calculations.