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Updated: Apr 12, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
Published on: February 15, 2016
Stereoselective construction of coconformational mechanically helical and topologically chiral [2]catenanes induced
Haitong Tang1, Yan Zou1, Hai-Ning Zhang1
1State Key Laboratory of Molecular Engineering of Polymers, Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Department of Chemistry, Fudan University, Shanghai 200433, People's Republic of China.
Abstract:
Supported by chiral stationary phase high-performance liquid chromatography HPLC (CSP-HPLC), examples of chiral mechanically interlocked organic molecules, including knots, rotaxanes, and catenanes, have been reported. However, the exploration of stereoselective construction of chiral cationic complexes, particularly those induced by point chirality, has been notably limited due to the constraints posed by the type of chiral chromatographic columns and separation efficiency. To address this, we have developed a construction strategy for generating coconformational mechanically helical and topologically chiral [2]catenanes through the induction of point chirality. In this study, by adjusting the symmetry of the ligand, we have easily realized the efficient construction of high-yield crystalline coconformational mechanically helical and topologically chiral [2]catenanes. Moreover, within the enantiomerically pure chiral environment of molecular self-assembly driven by L-alanine and L-valine residues in bidentate ligands, the coconformational mechanically helical and topologically chiral [2]catenanes exist exclusively as a single enantiomer, thus eliminating the need for laborious CSP-HPLC separation from racemic mixtures. The generation of the opposite enantiomer can be realized by employing unsymmetrical ligands containing corresponding D-alanine and D-valine residues, as confirmed through single-crystal X-ray diffraction, elemental analysis, electrospray-ionization time-of-flight mass spectrometry, solution-state NMR spectroscopy, and circular dichroism spectroscopy.
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