Efficient preparation and properties of triazole-linked corannulene derivatives

In this study, we explore the potential of copper(I)-catalyzed cycloaddition reaction between azides and terminal alkynes to prepare corannulene-rich materials. For this purpose, a practical route is established to yield corannulene-based azide building blocks. The newly prepared corannulene-azides are then coupled with known corannulene-alkynes. The chemical yields of the dimerization reactions ranged from 80 to 90%. In this way, a number of triazole-linked corannulene derivatives varying in the geometry, length, and the triazole-content are prepared. These results suggest that alkyne-azide click reaction can serve as a useful synthetic tool in the preparation of corannulene-rich discrete oligomers as well as polymers. (C) 2012 Elsevier Ltd. All rights reserved.