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Binary Supramolecular Chirality “1/0” Switched by Hierarchical Photoisomerization of a Flower‐Like Compound with a Binaphthol Core and Alkyl‐Functionalized Azobenzene Side Chains
Author(s) -
Hou Jiaxin,
Liao Jinglun,
Feng Yancong,
Feringa Ben L.,
Chen Jiawen,
Li Hao,
Zhou Guofu
Publication year - 2020
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202000049
Subject(s) - photoisomerization , azobenzene , chirality (physics) , supramolecular chirality , liquid crystal , materials science , supramolecular chemistry , moiety , alkyl , photochromism , side chain , photochemistry , crystallography , chemistry , stereochemistry , crystal structure , nanotechnology , isomerization , organic chemistry , physics , chiral symmetry breaking , optoelectronics , catalysis , quantum mechanics , nambu–jona lasinio model , quark , polymer , composite material
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.