Synthesis and Self-Assembly of 6,13-Bis(alkylthio)pentacene Derivatives

Abstract

6,13-Bis(alkylthio)pentacenes directed toward OFET were synthesized by the ZnI2-mediated reaction of trans-6,13-dihydroxy-6,13-dihydropentacene with alkylthiols, followed by the dehydrogenative aromatization of the resulting trans-6,13-bis(alkylthio)-6,13-dihydropentacenes with p-chloranil. The X-ray crystallographic analysis of 6,13-bis(methylthio)pentacene reveals that this compound is arranged as a result of cofacial pi-stacking with S-S and S-pi interactions.