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

Authors
Zhang, XinKo, GyeongjuJoung, Joonyoung F.Li, MengJeong, YerinSwamy, K. M. K.Lee, DayoungLiu, YifanLee, SongyiPark, SungnamJames, Tony D.Yoon, Juyoung
Issue Date
7-12월-2018
Publisher
ROYAL SOC CHEMISTRY
Citation
CHEMICAL COMMUNICATIONS, v.54, no.94, pp.13264 - 13267
Indexed
SCIE
SCOPUS
Journal Title
CHEMICAL COMMUNICATIONS
Volume
54
Number
94
Start Page
13264
End Page
13267
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/71227
DOI
10.1039/c8cc06262e
ISSN
1359-7345
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.
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