Dynamic self-inclusion behavior of pillar[5]arene-based pseudo[1]rotaxanes

Abstract

It was found that spontaneous isomerization takes place between three isomers of a pillar[5]arene (P5)-based pseudo[1]rotaxane. The isomerization process could be monitored by (1)H NMR spectra in polar solvent and the geometric configurations of the three isomers were further evaluated by theoretical calculations. In the threaded forms, the alkyl side chain might be preorganized by intramolecular N-HO bonds between the urea group of the side chain and the methoxy group of the P5 and further stabilized by multiple interactions, including H-bonding, C-H∙∙∙π interactions, and the steric effect of the N-Boc moiety. These cooperative interactions greatly enhance the stability of the threaded form in polar solvent, and endow it with very special self-inclusion behavior.