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

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 (KR(S)/KS(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 (|glum| up to 1.4×10-3) in water. Notably, corral[4]BINOL exhibits high recognition affinity up to 8.6×1010 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, facile accessibility, together with the superior fluorescent and chiroptical properties, endow corral[4]BINOL with great potentials for a wide range of applications.