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Cyclization of an Achiral Flipping Panel to Homochiral Tubes Exhibiting Circularly Polarized Luminescence |
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| Authors: | Mengdi Lin Lifang Bian Qing Chen Houyang Xu Zhichang Liu Prof Dr Kelong Zhu |
| Institution: | 1. School of Chemistry, Sun Yat-Sen University, 510275 Guangzhou, China;2. Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University
Westlake Institute for Advanced Study, 600 Dunyu Road, 310030 Hangzhou, Zhejiang, China;3. Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University |
| Abstract: | Macrocyclization of the bendable 2,7-dimethoxythianthrene with methylene linkages afforded a pair of homochiral macrocycles featuring a hex-nut-like geometry. Their structures were fully characterized by NMR spectroscopy, mass spectrometry, and single-crystal X-ray diffraction analysis. Their stable planar chirality facilitates efficient resolution of the pair of enantiomers which could be readily derivatized. Installing phenylethynyl groups on their rims leads to luminescent tubular macrocycles exhibiting circularly polarized luminescence with a large dissymmetry value |glum| of 5×10−3. Supramolecular binding of electron-deficient guests by the tube results in fluorescence quenching, which proved its potential for the future development of switchable chiroptical systems. |
| Keywords: | Chirality Macrocycle Supramolecule Thianthrene Tube |