A Facile Approach to New Vinylogous Tetrathiafulvalene (TTF) Derivatives: 2,3-Bis(1,3-dithiole-2-ylidene)succinonitriles

Abstract

A new approach to vinylogous TTF derivatives 5 via an alkyne-coupling reaction is reported. Their fundamental redox behavior has been studied. A proposed reaction mechanism, which accounts for the formation of compounds 5 is discussed.

Key words

cycloadditions - substituent effects - sulfur - synthesis - vinylogous tetrathiafulvalene

References

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7

Slow evaporation of the solution of 5b in CH₂Cl₂ gave single crystals suitable for X-ray diffraction measurement. Crystal data for compound 5b: C₁₄H₁₂N₂S₈, MW = 464, monoclinic, C ₂, a = 16.527 (2), b = 5.2211 (6), c = 12.897 (2) Å; β = 118.955 (13)°, V = 973.8 (2) ų, T = 153 (2) K, Z = 2, D_c = 1.585 g·cm^-3, µ = 0.917 mm^-1, λ = 0.71073 Å, F(000) = 476, independent reflections (R _int = 0.1017), 3870 reflections collected; refinement method, full-matrix least-squares refinement on F²; goodness-of-fit on F ² = 0.761; Final R indices [I > 2σ(I)] R1 = 0.048, wR2 = 0.118.