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

Sheng Wang, Siyu Xie, Hua Zeng, Hongxu Du, Jie Zhang, Xinhua Wan

2022Angewandte Chemie14 citationsDOI

Abstract

Abstract Chiral recognition is of 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 the polyphenylacetylene backbone and the thus triggered fluorescence. Owing to the high selectivity, this visual process can recognize structurally diverse achiral amines and quantitatively check the impurity content. It also shows an outstanding enantioselectivity towards various chiral amines and can be applied to determine enantiomeric composition. The multiple responses in absorption, circular dichroism, photoluminescence, and circularly polarized luminescence make the helical transition of the polymer backbone a potential detection mode for high‐throughput screening of chiral chemicals.

Topics & Concepts

Circular dichroismEnantiomerAmine gas treatingPhotoluminescenceLuminescenceChemistryEnantiomeric excessSelectivityCombinatorial chemistryImpurityChirality (physics)FluorescencePhotochemistryEnantioselective synthesisCatalysisOrganic chemistryMaterials scienceStereochemistryOptoelectronicsPhysicsNambu–Jona-Lasinio modelQuarkChiral symmetry breakingQuantum mechanicsSynthesis and Properties of Aromatic CompoundsLuminescence and Fluorescent MaterialsPolydiacetylene-based materials and applications
Self‐Reporting Activated Ester‐Amine Reaction for Enantioselective Multi‐Channel Visual Detection of Chiral Amines | Litcius