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Self-Reporting Activated Ester-Amine Reaction for Enantioselective Multi-Channel Visual Detection of Chiral Amines.

Chiral recognition is of pivotal importance not only in living systems but also in estimating the optical purity of enantiomeric drugs and fabricating advanced materials. Herein we report a novel self-reporting activated ester-amine reaction that can provide multi-channel visual detection of organic amines. It relies on the reaction extent dependent cis-transoid to cis-cisoid helical transition of polyphenylacetylene backbone and thus triggered fluorescence. Owing to the high selectivity, this visual process can recognize structurally diverse achiral amines and quantitatively checkout the impurity content. Moreover, it also exhibits an outstanding enantioselectivity towards various chiral amines and can be applied to determine enantiomeric composition. The multiple responses in absorption, circular dichromism, photoluminescence, and circularly polarized luminescence make the helical transition of polymer backbone potential as a novel detection mode for high throughput screening of chiral chemicals.