Holding of planar chirality of pillar[5]arene by kinetic trapping using host–guest interactions with achiral guest solvents

Abstract

We report a solvent-dependent switching and holding of planar chirality of pillar[5]arene with stereogenic carbons at both rims by host–guest complexation with achiral guest solvents. The planar chirality could be held for a given length of time at 25 °C in long linear guest solvents by kinetic trapping through host–guest complexation. The kinetic trapping worked at 25 °C, but not at 60 °C, thus a planar-chiral inversion using kinetic trapping based on host–guest complexation in the long linear solvents was demonstrated.