Schiff Base Route to Stackable <i>Pseudo</i>-Triphenylenes: Stereoelectronic Control of Assembly and Luminescence

Tandem tautomerization-trapping of isomeric mixtures of tris(N-salicylideneamine)s facilitated access to a new class of discotic molecules that are geometrically analogous to 2,6,10-trisubstituted triphenylenes. The shape and electrostatic complementarity associated with the molecular C3 symmetry assists cofacial stacking of π-faces to afford either infinite one-dimensional columns or discrete dimeric capsules. Structural reinforcement achieved by such interlocked geometry resulted in significant fluorescence enhancement upon aggregation in solution, as determined by dynamic light scattering and fluorescence spectroscopy.