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

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 esteramine 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.

Metal-Enhanced Helical Chirality of Coil Macromolecules: Bioinspired by Metal Coordination-Induced Protein Folding

“…The half-width of the cis CC bond gradually broadened in the Raman spectrum, and the wavelength of cis CC bond blue-shifted from 1614 to 1628 cm –1 for poly-( l - co - d )-ala-Boc. The results show that the regularity of the π–π helical polyacetylene skeleton was reduced according to the studies reported by Wan and Tabata. − The blue shift indicated that the extended conjugation changed to contracted conjugation in the backbone of poly-( l - co - d )-ala-Boc.…”

Brightening up Full-Color and White Circularly Polarized Luminescence through Chiral Induction and Circularly Polarized Light Excitation

“…CPL materials have been widely concerned by researchers due to their huge potential applications in 3D optical display, information storage and encryption, biological probes, and so forth. − Circularly polarized light can be generated from plane polarized light by using polarizers and quarter wave plates, but it will cause large energy loss in the transition process. , Therefore, the development of materials that can directly generate CPL has become a new research hotspot. At present, the methods to construct CPL-active materials mainly focus on small organic molecules, , supramolecular components, − liquid crystals, polymers, ,− and metal–ligand coordination complexes. , CPL materials based on polymers have advanced greatly due to their high stability and good processability .…”

Diastereomeric multi‐chiral pendant groups: Their key role in stimuli‐responsive polymeric responses

“… 1 , 2 In consequence, a large variety of non‐natural foldamers and helical polymers have been studied during the last decades. In the special case of helical polymers, families such as poly(isocyanide)s, 3 poly(isocyanate)s, 4 poly(diphenylacetylene)s, 5 , 6 or polyacetylenes, 7 , 8 among others, provide a large variety of helical scaffolds with different static/dynamic, which properties find applications in different fields such as chiral materials asymmetric catalysis, 9 , 10 , 11 , 12 , 13 chiral recognition, 14 , 15 circular polarized luminescence (CPL) sources, 5 , 6 , 15 , 16 chiroptical switches, 17 , 18 or chiral stationary phases for high performance liquid chromatography (HPLC) among others. 19 , 20 , 21 To be functional, these helical polymers must adopt macromolecular helical structures with screw sense excess.…”