Macroscopic Chirality of Supramolecular Gels Formed from Achiral Tris(ethyl cinnamate) Benzene-1,3,5-tricarboxamides

A C3‐symmetric benzene‐1,3,5‐tricarboxamide substituted with ethyl cinnamate was found to self‐assemble into supramolecular gels with macroscopic chirality in a DMF/H2O mixture. The achiral compound simultaneously formed left‐ and right‐handed twists in an unequal number, thus resulting in the macro...

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Published inAngewandte Chemie Vol. 126; no. 49; pp. 13642 - 13646
Main Authors Shen, Zhaocun, Wang, Tianyu, Liu, Minghua
Format Journal Article
LanguageEnglish
German
Published Weinheim WILEY-VCH Verlag 01.12.2014
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
Subjects
Achirale Moleküle
Additives
Amines
Assemblies
Broken symmetry
Chemistry
Chirality
Chiralität
Exchange
Gele
Gels
Handedness
Molecular structure
Selbstorganisation
Symmetriebruch
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Summary:A C3‐symmetric benzene‐1,3,5‐tricarboxamide substituted with ethyl cinnamate was found to self‐assemble into supramolecular gels with macroscopic chirality in a DMF/H2O mixture. The achiral compound simultaneously formed left‐ and right‐handed twists in an unequal number, thus resulting in the macroscopic chirality of the gels without any chiral additives. Furthermore, ester–amide exchange reactions with chiral amines enabled the control of both the handedness of the twists and the macroscopic chirality of the gels, depending on the structures of the chiral amines. These results provide new prospects for understanding and regulating symmetry breaking in assemblies of supramolecular gels formed from achiral molecular building blocks. Die Selbstorganisation achiraler und C3‐symmetrischer Benzol‐1,3,5‐tricarboxamide (BTAC) in DMF/H2O ergab ohne chirale Dotanden supramolekulare Gele mit makroskopischer Chiralität. Die ungleiche Zahl rechts‐ und linksgängiger Windungen und die daraus resultierende makroskopische Chiralität konnten außerdem durch Amid‐Ester‐Austausch gesteuert werden.
Bibliography:Chinese Academy of Sciences
We gratefully acknowledge funding of this research by the Basic Research Development Program (2013CB834504), the National Natural Science Foundation of China (Nos. 91027042, 21321063 and 21227802), "Strategic Priority Research Program" of the Chinese Academy of Sciences (XDA09020102, XDB12020200), and the Fund of the Chinese Academy of Sciences.
Chinese Academy of Sciences - No. XDA09020102; No. XDB12020200
istex:7D7C231A70A7669DC323269A6DC2E1B9C5E7618E
Basic Research Development Program - No. 2013CB834504
ark:/67375/WNG-1XNPXFPS-D
National Natural Science Foundation of China - No. 91027042; No. 21321063; No. 21227802
ArticleID:ANGE201407223
We gratefully acknowledge funding of this research by the Basic Research Development Program (2013CB834504), the National Natural Science Foundation of China (Nos. 91027042, 21321063 and 21227802), “Strategic Priority Research Program” of the Chinese Academy of Sciences (XDA09020102, XDB12020200), and the Fund of the Chinese Academy of Sciences.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201407223