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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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Publication details

The article was received on 01 Aug 2018, accepted on 02 Nov 2018 and first published on 02 Nov 2018


Article type: Communication
DOI: 10.1039/C8CC06262E
Citation: Chem. Commun., 2018, Advance Article
  • Open access: Creative Commons BY license
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    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, Advance Article , DOI: 10.1039/C8CC06262E

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