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Enantiopure Corral[4]BINOLs as Ultrastrong Receptors for Recognition and Differential Sensing of Steroids

Rong Fu, Dai‐Yuan Li, Jia‐Hong Tian, Yi‐Lin Lin, Qingyu Zhao, Wenli Li, Fangyuan Chen, Dong‐Sheng Guo, Kang Cai

2024Angewandte Chemie International Edition35 citationsDOIOpen Access PDF

Abstract

Abstract The precise recognition and sensing of steroids, a type of vital biomolecules, hold immense practical value across various domains. In this study, we introduced corral[4]BINOLs ( C[4]BINOL s), a pair of enantiomeric conjugated deep‐cavity hosts, as novel synthetic receptors for binding steroids. Due to the strong hydrophobic effect of their deep nonpolar, chiral cavities, the two enantiomers of C[4]BINOL s demonstrated exceptionally high recognition affinities (up to 10 12 M −1 ) for 16 important steroidal compounds as well as good enantioselectiviy (up to 15.5) in aqueous solutions, establishing them as the most potent known steroid receptors. Harnessing their ultrahigh affinity, remarkable enantioselectivity, and fluorescence emission properties, the two C[4]BINOL enantiomers were employed to compose a fluorescent sensor array which achieved discrimination and sensing of 16 structurally similar steroids at low concentrations.

Topics & Concepts

Enantiopure drugDifferential (mechanical device)ReceptorChemistryMolecular recognitionComputational biologyBiologyBiochemistryPhysicsMoleculeOrganic chemistryEnantioselective synthesisThermodynamicsCatalysisMolecular Sensors and Ion DetectionSupramolecular Chemistry and ComplexesLuminescence and Fluorescent Materials
Enantiopure Corral[4]BINOLs as Ultrastrong Receptors for Recognition and Differential Sensing of Steroids | Litcius