Bulletin of the Chemical Society of Japan p. 1547 - 1555 (1989)
Update date:2022-08-11
Topics:
Yui, Koji
Ishida, Hideki
Aso, Yoshio
Otsubo, Tetsuo
Ogura, Fumio
et al.
Novel heteroquinoid compounds as potential electron acceptors, 2,5-bis(dicyanomethylene)-2,5-dihydrothieno<3,2-b>thiophene (4a), 3,6-dibromo derivative, 2,6-bis(dicyanomethylene)-2,6-dihydrothieno<3,2-b:2',3'-d>thiophene, 3,5-dibromo derivative, and 4,4-dioxide were synthesized by the action of tetracyanoethylene oxide or by a Pd(0)-catalyzed substitution reaction with sodium dicyanomethanide on the corresponding α,α'-dihalo-substituted fused thiophenes.They show effectively diminished on-site Coulomb repulsion owing to the extensive conjugation, and most of their molecular complexes with various electron donors exhibit very high electrical conductivies up to metallic region.In addition, X-ray crystallographic analysis of the complex of 4a with bis(ethylenedithio)tetrathiafulvalene has elucidated that sulfur atoms embedded in 4a molecule are capable of inducing a significant intermolecular interaction, forming a sheet-like network structure.
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