A Chiral Emissive Conjugated Corral for High‐Affinity and Highly Enantioselective Recognition in Water

作者：Rong Fu, Qingyu Zhao, Han Han, Wenli Li, Fangyuan Chen, Chun Tang, Wei Zhang, Si‐Dan Guo, Dai‐Yuan Li, Wen‐Chao Geng, Dong‐Sheng Guo, Kang Cai · 发表于：Angewandte Chemie International Edition · 年份：2023 · DOI：10.1002/anie.202315990 · 被引用次数：68 · 研究领域：Molecular spectroscopy and chirality、Molecular Sensors and Ion Detection、Crystallography and molecular interactions

Abstract Accurately distinguishing between enantiomeric molecules is a fundamental challenge in the field of chemistry. However, there is still significant room for improvement in both the enantiomeric selectivity (K R ( S ) /K S ( R ) ) and binding strength of most reported macrocyclic chiral receptors to meet the demands of practical application scenarios. Herein, we synthesized a water‐soluble conjugated tubular host—namely, corral[4]BINOL—using a chiral 1,1′‐bi‐2‐naphthol (BINOL) derivative as the repeating unit. The conjugated chiral backbone endows corral[4]BINOL with good fluorescent emission (QY=34 % ) and circularly polarized luminescence (| g lum | up to 1.4×10 −3 ) in water. Notably, corral[4]BINOL exhibits high recognition affinity up to 8.6×10 10 M −1 towards achiral guests in water, and manifested excellent enantioselectivity up to 18.7 towards chiral substrates, both of which represent the highest values observed among chiral macrocycles in aqueous solution. The ultrastrong binding strength, outstanding enantioselectivity, and facile accessibility, together with the superior fluorescent and chiroptical properties, endow corral[4]BINOL with great potential for a wide range of applications.