Cyclization of an Achiral Flipping Panel to Homochiral Tubes Exhibiting Circularly Polarized Luminescence

被引：19

作者：

Lin, Mengdi ^{[1
]}

Bian, Lifang ^{[2
,3
]}

Chen, Qing ^{[1
]}

Xu, Houyang ^{[1
]}

Liu, Zhichang ^{[2
,3
]}

Zhu, Kelong ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Chem, Guangzhou 510275, Peoples R China

[2] Westlake Univ, Key Lab Precise Synth Funct Mol Zhejiang Prov, Sch Sci, Dept Chem, 600 Dunyu Rd, Hangzhou 310030, Zhejiang, Peoples R China

[3] Westlake Inst Adv Study, 600 Dunyu Rd, Hangzhou 310030, Zhejiang, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 28期

基金：

中国国家自然科学基金;

关键词：

Chirality; Macrocycle; Supramolecule; Thianthrene; Tube; RECOGNITION; THIANTHRENE; HOSTS;

D O I：

10.1002/anie.202303035

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 |g(lum)| of 5x10(-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.

引用

页数：5

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