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/H2 O 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.
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Shen et al. (2014) studied this question.