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J Am Chem Soc. 2006 Aug 30;128(34):10986-7.

Schiff base route to stackable pseudo-triphenylenes: stereoelectronic control of assembly and luminescence.

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  • 1Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405, USA.


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 pi-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.

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