Macrocyclic polyethers incorporating resorcinol residues as templates for cyclobis(paraquat-p-phenylene) in the self-assembly of [2]catenanes

Abstract

The self-assembly of [2]catenanes incorporating cyclobis(paraquat-p-phenylene) and either bis(metaphenylene)-32-crown-10 or tris(metaphenylene)-48-crown-15 has been achieved. The dynamic processes associated with the relative motions of the two rings have been studied by variable temperature 1H NMR spectroscopy. Both [2]catenanes display rapid relative movements of the two components, associated with free energies of activation in the region 12–14 kcal mol-1 for different processes. The resorcinol residues of the macrocyclic polyethers are bound in the cavity of the cyclophane by π-π stacking, electrostatic interactions, and T-type hydrogen bonding. © 1995, Taylor & Francis Group, LLC. All rights reserved.