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Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
Published on: February 15, 2016
Chiral Dominance in Supramolecular Co-assemblies via Cation-π Driven Stereochemical Locking
Xiaoqin Zhou1,2, Qianqian Huang1, Cui Ye1
1School of Chemistry and Chemical Engineering, Key Laboratory of Clean Energy Materials Chemistry of Guangdong Higher Education Institutes, Lingnan Normal University, Zhanjiang, 524048, P. R. China.
None:
Controlling supramolecular chirality in multicomponent systems remains a significant challenge due to competing stereochemical interactions. In this study, we report a case of competitive chiral dominance in binary co-assemblies composed of enantiomeric tartaric acid derivatives (a1 and a2) and enantiomeric pyridine derivatives (R/S-py). The dibenzoyl-substituted tartaric acid (a1) is capable of overriding the chirality of the co-assemblies by protonating the chiral pyridines to form pyridinium-carboxylate pairs. This interaction induces in situ cation-π interactions, leading to the formation of stereoconfiguration-locked H-aggregates. In contrast, the pivaloyl-substituted tartaric acid (a2) exhibits chirality bias governed by the enantiopure pyridine derivatives, attributed to its increased steric bulk and the absence of cation-π interactions. These findings not only advance the fundamental understanding of stereochemical communication but also offer a new strategy for controlling hierarchical chirality in complex supramolecular systems.
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