Solvent-Driven Chiral-Interaction Reversion for Organogel Formation

Solvent-Driven Chiral-Interaction Reversion for Organogel Formation

For chiral gels and related applications, one of the critical issues is how to modulate the stereoselective interaction between the gel and the chiral guest precisely, as well as how to translate this information into the macroscopic properties of materials. Herein, we report that this process can a...

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Bibliographic Details
Published in:Angewandte Chemie International Edition Vol. 53; no. 8; pp. 2124 - 2129
Main Authors: Qing, Guangyan, Shan, Xingxing, Chen, Wenrui, Lv, Ziyu, Xiong, Peng, Sun, Taolei
Format: Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 17-02-2014
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Edition:International ed. in English
Subjects:
Assembly
chiral gels
chiral recognition
Complexation
Design engineering
Dipeptides - chemistry
Enantiomers
Formations
Gels
Gels - chemistry
host-guest systems
Material properties
Materials selection
Quinidine - chemistry
Quinine
Reversion
Self assembly
solvent effects
Solvents
Solvents - chemistry
Stereoisomerism
Stereoselectivity
Thermodynamics
self-assembly
solvent effects
chiral recognition
host-guest systems
chiral gels
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Summary:For chiral gels and related applications, one of the critical issues is how to modulate the stereoselective interaction between the gel and the chiral guest precisely, as well as how to translate this information into the macroscopic properties of materials. Herein, we report that this process can also be modulated by nonchiral solvents, which can induce a chiral‐interaction reversion for organogel formation. This process could be observed through the clear difference in gelation speed and the morphology of the resulting self‐assembly. This chiral effect was successfully applied in the selective separation of quinine enantiomers and imparts “smart” merits to the gel materials. Get smart: A system for gel formation in which the solvent not only provides a medium but also determines the nature of the stereoselective interaction between a gelator and a chiral guest provides important insight into the assembly of chiral gelators. The solvent‐driven preferential complexation of one or another chiral guest (see picture) enables the design of organogels with new “smart” features for various applications.
Bibliography:istex:4061EEEF0BD935EE06F1C0961C04439059266E24
ark:/67375/WNG-VPFCX7K3-0
Major State Basic Research Development Program of China - No. 2013CB933002
National Natural Science Foundation of China - No. 21104061; No. 21275114; No. 91127027; No. 51173142
ArticleID:ANIE201308554
We thank the National Natural Science Foundation of China (21104061, 21275114, 91127027, 51173142) and the Major State Basic Research Development Program of China (973 Program; 2013CB933002) for funding. G. Qing acknowledges Hubei Provincial Department of Education for financial assistance through the "Chutian Scholar" program. We also thank Prof. J. Sun at Wuhan University for his help with theoretical calculations, and Dr. X. J. Wu for his help in the analysis of 1H-13C and 1H-1H COSY NMR spectra.
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These authors contributed equally.
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We thank the National Natural Science Foundation of China (21104061, 21275114, 91127027, 51173142) and the Major State Basic Research Development Program of China (973 Program; 2013CB933002) for funding. G. Qing acknowledges Hubei Provincial Department of Education for financial assistance through the “Chutian Scholar” program. We also thank Prof. J. Sun at Wuhan University for his help with theoretical calculations, and Dr. X. J. Wu for his help in the analysis of
C and
H COSY NMR spectra.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201308554