Pillararene Host–Guest Complexation Induced Chirality Amplification: A New Way to Detect Cryptochiral Compounds

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...

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Veröffentlicht in:Angewandte Chemie International Edition Jg. 59; H. 27; S. 10868 - 10872
Hauptverfasser: Zhu, Huangtianzhi, Li, Qi, Gao, Zongchun, Wang, Hongliang, Shi, Bingbing, Wu, Yitao, Shangguan, Liqing, Hong, Xin, Wang, Feng, Huang, Feihe
Format: Journal Article
Sprache:Englisch
Veröffentlicht: Germany Wiley Subscription Services, Inc 26.06.2020
Ausgabe:International ed. in English
Schlagworte:
Amplification
chiral amplification
Chirality
circular dichroism
Complexation
Density functional theory
host–guest systems
pillararenes
Spectroscopy
Supramolecular compounds
chiral amplification
host-guest systems
circular dichroism
chirality
pillararenes
ISSN:1433-7851, 1521-3773, 1521-3773
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Zusammenfassung: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. Intrinsic advantages and uniqueness in chirality amplification are exhibited by pillararenes. By combining high affinity for guests, detectable UV absorption, and inducible chirality they can be used for detecting cryptochiral compounds.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202001680