Guest-regulated chirality switching of planar chiral pseudo[1]catenanes

Org Biomol Chem. 2018 Mar 28;16(12):2028-2032. doi: 10.1039/c8ob00156a. Epub 2018 Feb 20.

Abstract

pseudo[1]Catenane 3 is in a self-included conformation in chloroform, but in dichloromethane, it exists in an equilibrium between the self-included conformational state and a de-threading one. The planar chirality inversion of 3 can be triggered by the host-guest complexation of 3 with adiponitrile G, but the extent of such chiral switching depends on the length of self-included bis(pyrazin-2-yloxy)alkane chains in 3 - longer chains are more favored than shorter ones in the inversion.