Structural Effects of an Imine-bridging Station on Construction Imine-bridged Rotaxanes and Their Dynamic Equilibrium upon Hydrolysis of the Imine Bonds

Abstract

Developments of diverse protocols for the preparation of interlocked molecules are increasing in importance because of their promising applications as molecular devices. We previously reported novel rotaxane synthesis based on imine bond between an hydrindacene axle molecule and a ring molecule, and the control of subunit mobility based on hydrolysis of the imine bonds. Here we report the structural effects of axle and ring components on imine bond formation/breaking properties using newly prepared a cyclohexane- and a hexahydropyrene-type axle molecules in place of the hydrindacene axle. Proportion of the hexahydropyrene-type [2]rotaxane in the equilibrated mixture under acidic hydrolytic conditions is higher for the new derivative than for the previous hydrindacene-type [2]rotaxane.