Star-shaped pyrrole-fused tetrathiafulvalene oligomers: synthesis and redox, self-assembling, and conductive properties

A series of star-shaped pyrrole-fused tetrathiafulvalene (TTF) oligomers 1-3 was synthesized via an S(N)Ar reaction of fluorinated benzenes with the pyrrolyl sodium salts. Electrochemical and chemical oxidations of 1-3 revealed that a radical cation moiety on each TTF unit was successfully accumulated in all oligomers. Self-assembled structures of neutral and oxidized species were characterized by SEM and XRD, and their conductive properties of the iodine-doped 1-3 as well as an intermolecular mixed-valence ion radical salt were investigated.