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Liang, Haozhong; Hua, Bin; Xu, Fan; Gan, Li-She; Shao, Li; Huang, Feihe
Journal of the American Chemical Society, 11/2020, Letnik: 142, Številka: 46Journal Article
Stimuli-responsive unimolecular chirality switching is a highly intriguing topic because the molecular structure as well as its function can be adjusted simultaneously by a switching process. Herein, a novel acid/base-tunable unimolecular chirality switching system based on a pillar5azacrown pseudo1catenane is reported. The bicyclic pillar5azacrown pseudo1catenane PN4 is synthesized through fusing an azacrown ring onto one repeating unit of a pillar5arene. Protonation and deprotonation can reversibly regulate the conformational transformations of PN4 between self-inclusion and self-exclusion structures, which results in the chiroptical inversions of the pseudo1catenane. NMR spectra, circular dichroism spectra, and single-crystal structures demonstrate these processes. This pseudo1catenane is a novel pillararene-based unimolecular chirality switching system driven by acid/base responsiveness and reveals a new perspective on the supramolecular chirality chemistry of macrocycles.
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