Beijing National Laboratory for Molecular Science (BNLMS) CAS Key Laboratory of Colloid, Interface and Chemical Thermodynamics Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 (P.R. China) http://liumh.iccas.ac.cn/
Angew Chem Int Ed Engl. 2014 Dec 1;53(49):13424-8. doi: 10.1002/anie.201407223. Epub 2014 Oct 5.
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.
一种 C3 对称的苯-1,3,5-三羧酸酰胺取代了肉桂酸乙酯，被发现可以在 DMF/H2O 混合物中自组装成具有宏观手性的超分子凝胶。该非手性化合物同时以不等数量形成了左旋和右旋扭曲，从而在没有任何手性添加剂的情况下产生了凝胶的宏观手性。此外，通过酯酰胺交换反应与手性胺反应，可以控制扭曲的手性和凝胶的宏观手性，这取决于手性胺的结构。这些结果为理解和调节由非手性分子构建块形成的超分子凝胶组装体中的对称破缺提供了新的前景。
