MACROCYCLIC POLYETHERS INCORPORATING RESORCINOL RESIDUES AS TEMPLATES FOR CYCLOBIS(PARAQUAT-P-PHENYLENE) IN THE SELF-ASSEMBLY OF [2]CATENANES

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 H-1 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 pi-pi stacking, electrostatic interactions, and T-type hydrogen bonding.