Design of reversible organic–organometallic multi-redox systems using thianthrene having ferrocene fragments

1-Ferrocenyl- and 1,9-diferrocenyl-thianthrenes have been synthesized by using palladium-catalyzed cross-coupling reactions of 1-bromo- and 1,9-dibromo-thianthrenes with ferrocenylzinc chloride. The structure of 1-ferrocenylthianthrene was determined by X-ray crystallographic analysis. 1-Ferrocenyl- and 1,9-diferrocenyl-thianthrenes show well-defined separated two-steps two-electrons and three-steps three-electrons reversible redox waves derived from the ferrocenium cation and the thianthrene radical cation, respectively, by the cyclic voltammetry in dichloromethane containing the supporting electrolyte anion of [B(C6F5)4]−.