Chiral macrocycles forming high-affinity host-guest homoternary complexes for chiral discrimination and amplified circularly polarized luminescence

Rong Fu, Fang-Yuan Chen, Le Dai, Dai-Yuan Li, Qing-Yu Zhao, Si-Dan Guo, Zi-Hang Song, Li-Bo Jing, Heng Wang, Xiaopeng Li, Dong-Sheng Guo and Kang Cai ()
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Rong Fu: Nankai University
Fang-Yuan Chen: Nankai University
Le Dai: University of Chinese Academy of Sciences, Chinese Academy of Sciences
Dai-Yuan Li: Nankai University
Qing-Yu Zhao: Nankai University
Si-Dan Guo: Nankai University
Zi-Hang Song: Nankai University
Li-Bo Jing: Nankai University
Heng Wang: University of Chinese Academy of Sciences, Chinese Academy of Sciences
Xiaopeng Li: University of Chinese Academy of Sciences, Chinese Academy of Sciences
Dong-Sheng Guo: Nankai University
Kang Cai: Nankai University

Nature Communications, 2025, vol. 16, issue 1, 1-11

Abstract: Abstract The development of macrocyclic hosts with high-affinity 1:2 recognition capabilities is crucial for advancing supramolecular chemistry and its applications. While cucurbit[8]uril (CB[8]) has long been recognized for its unparallel 1:2 binding affinity, its limitations—including poor solubility, difficulty to modify and lack of optical activity—have hindered broader utilization. Here, we introduce a class of enantiopure chiral macrocycles, RRRR- or SSSS-corral[4]BINOL (C[4]Bs), which exhibit remarkable 1:2 recognition properties in water that are comparable or even surpass CB[8]. Using UV-Vis, fluorometric, and isothermal titration calorimetry (ITC), we demonstrate that C[4]Bs form stable homoternary complexes with 11 singly positively charged planar aromatic guests, with binding affinities up to 1017 M−2. These ultrahigh affinities make C[4]Bs versatile alternatives to CB[8], offering advantages such as superior water-solubility, ease of structural modification, and strong fluorescence. Furthermore, the unique chiral nature of C[4]Bs enables efficient fluorescent discrimination of chiral substrates and chirality transfer to non-chiral dyes, resulting in strong circularly polarized luminescence (CPL) with |glum | values up to 1.1 ×10−2. This study establishes C[4]Bs not only as powerful hosts for aqueous-phase supramolecular complexation but also as a promising platform for developing chiral functional materials.

Date: 2025
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DOI: 10.1038/s41467-025-64739-7

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