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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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2014-12, Vol.53 (49), p.13424-13428
Main Authors: Shen, Zhaocun, Wang, Tianyu, Liu, Minghua
Format: Article
Language:English
Subjects:
achiral molecules
Amines
Broken symmetry
Chirality
Dopants
Exchange
Gels
Handedness
Molecular structure
Self assembly
symmetry breaking
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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. The self‐assembly of achiral and C3‐symmetric benzene‐1,3,5‐tricarboxamides (BTAC) in DMF/H2O mixtures without any chiral dopants led to supramolecular gels that showed macroscopic chirality. The unequal number of left‐ and right‐handed twists and thus the macroscopic chirality of the gels could be controlled through amide–ester exchange reactions.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201407223