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Pillararene Host–Guest Complexation Induced Chirality Amplification: A New Way to Detect Cryptochiral Compounds
Author(s) -
Zhu Huangtianzhi,
Li Qi,
Gao Zongchun,
Wang Hongliang,
Shi Bingbing,
Wu Yitao,
Shangguan Liqing,
Hong Xin,
Wang Feng,
Huang Feihe
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202001680
Subject(s) - chirality (physics) , planar chirality , molecule , derivative (finance) , chemical physics , chemistry , nanotechnology , materials science , enantioselective synthesis , physics , organic chemistry , catalysis , chiral symmetry , quantum mechanics , financial economics , nambu–jona lasinio model , economics , quark
The contradiction between the rising demands of optical chirality sensing and the failure in chiral detection of cryptochiral compounds encourages researchers to find new methods for chirality amplification. Inspired by planar chirality and the host–guest recognition of pillararenes, we establish a new concept for amplifying CD signals of cryptochiral molecules by pillararene host–guest complexation induced chirality amplification. The planar chirality of pillararenes is induced and stabilized in the presence of the chiral guest, which makes the cryptochiral molecule detectable by CD spectroscopy. Several chiral guests are selected in these experiments and the mechanism of chiral amplification is studied with a non‐rotatable pillararene derivative and density functional theory calculations. We believe this work affords deeper understanding of chirality and provides a new perspective for chiral sensing.