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

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.