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. © 2010 The Royal Society of Chemistry.