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.
Highlights
Fluorescent chemosensors for sensing chiral molecules have been actively studied in recent years
We report a naphthoimidazolium-cholesterol derivative (NI-chol 1) as a fluorescence based chemosensor for chiral recognition, in which the naphthoimidazolium serves as a fluorophore and as a recognition moiety for anions via imidazolium (C–H)+–anion binding and the cholesterol unit acts as a chiral barrier
A distinct downfield shift 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
Summary
Fluorescent chemosensors for sensing chiral molecules have been actively studied in recent years. We report a naphthoimidazolium-cholesterol derivative (NI-chol 1) as a fluorescence based chemosensor for chiral recognition, in which the naphthoimidazolium serves as a fluorophore and as a recognition moiety for anions via imidazolium (C–H)+–anion binding and the cholesterol unit acts as a chiral barrier.
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