Synthesis of Stackable Pseudo-Triphenylenes

Significance

A series of stackable pseudo-tri­phenylenes has been made via a short, simple route involving an initial triple Schiff base condensation of 1,3,5-triformylphloroglucinol with an aromatic amine, followed by reaction with boron tri­fluoride and lithium diisopropylamide. Yields for both steps are high. The disk-like molecules were found to stack cofacially to form one-dimensional columns, the stacking mode being driven by cooperative electrostatic and steric interactions. These discotic molecules are also fluorescent, the efficiency of which increases upon aggregate formation in solution.