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Issue 94, 2018
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A naphthoimidazolium-cholesterol derivative as a ratiometric fluorescence based chemosensor for the chiral recognition of carboxylates

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Abstract

Fluorescent chemosensors for sensing chiral molecules have been actively studied in recent years. In the current study, we report a naphthoimidazolium-cholesterol derivative (NI-chol 1) as a fluorescence based chemosensor for chiral recognition, in which the naphthoimidazolium serves not only as a fluorophore but also as a recognition moiety for anions via imidazolium (C–H)+–anion binding and the cholesterol unit acts as a chiral barrier. In particular, NI-chol 1 displayed unique and distinct ratiometric changes with Boc-D-Phe, on the other hand, Boc-L-Phe induced a negligible change. Furthermore, a distinct downfield shift (from 9.64 ppm to 9.96 ppm) of the imidazolium C–H peak was observed for Boc-D-Phe (5 eq.) with severe broadening, which indicates strong ionic hydrogen bonding between the C–H proton and the carboxylate.

Graphical abstract: A naphthoimidazolium-cholesterol derivative as a ratiometric fluorescence based chemosensor for the chiral recognition of carboxylates

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Article information


Submitted
01 Aug 2018
Accepted
02 Nov 2018
First published
02 Nov 2018

This article is Open Access

Chem. Commun., 2018,54, 13264-13267
Article type
Communication

A naphthoimidazolium-cholesterol derivative as a ratiometric fluorescence based chemosensor for the chiral recognition of carboxylates

X. Zhang, G. Ko, J. F. Joung, M. Li, Y. Jeong, K. M. K. Swamy, D. Lee, Y. Liu, S. Lee, S. Park, T. D. James and J. Yoon, Chem. Commun., 2018, 54, 13264
DOI: 10.1039/C8CC06262E

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