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Synfacts 2006(11): 1123-1123
DOI: 10.1055/s-2006-949466
DOI: 10.1055/s-2006-949466
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Stackable Pseudo-Triphenylenes
J. A. Riddle, S. P. Lathrop, J. C. Bollinger, D. Lee*
Indiana University, Bloomington, USA
Further Information
Publication History
Publication Date:
24 October 2006 (online)

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.