Bromophenyl substituted dithiafulvenes and tetrathiafulvalene vinylogues: synthesis, structure, and electronic properties

Bis(bromophenyl) substituted tetrathiafulvalene vinylogues (TTFVs) were prepared via oxidative dimerization reactions of corresponding bromophenyl substituted dithiafulvene precursors. The synthesis of ortho-bromophenyl TTFVs led to the formation of an unexpected bis-spiro product, the structure of which was clearly elucidated by single crystal X-ray crystallography. Electronic and redox properties of the bromophenyl substituted dithiafulvenes, TTFV derivatives, and the related bis-spiro compound were investigated by UV–vis spectroscopic and cyclic voltammetric analyses. Detailed structure–property relationships have been discussed.