Guest-Induced Chirality Transfer in Trimers of Invertible Cylinder-Shaped Macrocycles

Abstract

Abstract Transfer of chiral information is abundant in biological processes. To mimic them in artificial systems, chiral macrocyclic molecules are particularly promising components for their simplicity and easy-to-predict intermolecular interactions. Herein, we report a chirality transfer system which shows turn-on chirality alignment of cylinder-shaped macrocycles with invertible chirality. The system is based on trimeric pillar[5]arene macrocycles linked covalently with alkyl chains. From a “native” state, the chirality changes to “off” and “on” states upon adding particular types of guest molecules for the macrocycle host components. Due to the weak inter-macrocycle interactions, the system can additionally switch the chirality from “on” state to “off” state, different from previous systems in which strong electrostatic interactions autonomously led to thermodynamically stable states.