Synthesis and shuttling behavior of rotaxanes consisting of crown ether wheel and disulfide dumbbell with two ammonium centers

Abstract

Several [2]- and [3]rotaxanes bearing some functional groups on their wheel components and spacers with different lengths between two ammonium centers on their dumbbell components were prepared in good yields from dibenzo-24-crown-8- ether derivatives and dumbbell-shaped bis(sec-ammonium salt)s having a centrally located disulfide linkage, by utilizing the reversible thiol-disulfide interchange reaction. The shuttling behaviors of the [2]rotaxanes were investigated by 1H NMR by use of the spin polarization transfer-selective inversion recovery technique. It was found that the change in spacer length in the axle resulted in a drastic change in shuttling rate of the [2]rotaxanes, although the introduction of the functional groups to the wheels did not affect the shuttling behavior at all.