Binary Supramolecular Chirality “1/0” Switched by Hierarchical Photoisomerization of a Flower-Like Compound with a Binaphthol Core and Alkyl-Functionalized Azobenzene Side Chains

Abstract

Chiral supramolecular assemblies are abundant in nature, but controlling the chirality of artificial systems still remains a challenge. In this work, we developed a system where supramolecular chirality can be controlled between chiral and achiral states, namely a chiral “1/0” switch using a flower-like azobenzene compound with a binaphthol core. Upon photoisomerization by ultraviolet irradiation, the terminal alkyl tails envelop the chiral “centre” with a reduction in the dihedral angle of the binaphthol moiety from 76.1° to 61.4°, like “closing petals”. In the doped liquid crystal E7 matrix, this hierarchical conformational transition prevents the transfer of chirality to the host liquid crystal, resulting in a degradation from cholesteric phase (HTP value: 13.84 μm−1) to an achiral nematic phase.