1,4-Dithiafulvene-substituted ferrocenes and their conversion into extended tetrathiafulvalene electron donors: synthetic, electrochemical and X-ray structural studies

Abstract

The synthesis of 1,4-dithiafulvene-substituted ferrocene derivatives 7, 11 and 12 by reaction of formyl-, diformyl- and diacetyl-ferrocene, respectively, with the carbanion generated from reagents 4a–c and the ylide prepared from reagent 5 is reported. Upon reaction with HCl–diethyl ether, compounds 7a–c undergo an oxidative dimerisation to yield extended tetrathiafulvalene (TTF) derivatives 8a–c. The solution electrochemistry of compounds 7, 8, 11, 12, 14 and 16 has been studied by cyclic voltammetry. The X-ray crystal structures of compounds 8b and 12a are presented.