Intermolecular Charge Transport in Self-Assembled Discs

Iyoda and co-workers report the synthesis of a disk-like molecule containing six electroactive tetrathiafulvalenes and demonstrate that they form self-assembled nanowires. In situ deprotection of the TMS groups followed by six Sonogashira reactions provides the desired compound in 52% overall yield (˜90% yield per coupling). Hexakis(trimethylsilylethynyl)benzene was previously synthesized by Tobe and co-workers in one step from hexabromobenzene (Org. Lett. 2001, 3, 2419-2421). One-electron chemical oxidation by Fe(ClO4)3 and self-assembly provided fibers with hexagonal columnar packing and a conductivity of 1.1 x 10-3 S/cm.