Synthesis, physical properties and self-assembly of star-shaped oligothiophenes-substituted and fused triphenylenes

Abstract

A series of star-shaped oligothiophene-attached and fused triphenylenes was synthesized. The synthesis was first conducted by six-fold Pd-catalyzed Stille cross-coupling reactions to yield the hexakis-oligothiophenes substituted triphenylenes TTP, TTP1, TTP2 and TTP3 and then followed by successful oxidative cyclodehydrogenation of TTP1 to generate the thiophene-fused triphenylene compound TTP1-C with an extended core. Their optical, electrochemical, thermal properties and self-assembly behaviors were investigated and the structure–property relationships were established, which clearly demonstrated the influence of the length of the peripheral oligothiophene units and the core structure on the electronic nature and solid-state packing of these star-shaped disc-like molecules.