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A naphthoimidazolium-cholesterol derivative as a ratiometric fluorescence based chemosensor for the chiral recognition of carboxylates
- A naphthoimidazolium-cholesterol derivative as a ratiometric fluorescence based chemosensor for the chiral recognition of carboxylates
- Zhang, Xin; Ko, Gyeongju; Joung, Joonyoung F.; Li, Meng; Jeong, Yerin; Swamy, K. M. K.; Lee, Dayoung; Liu, Yifan; Lee, Songyi; Park, Sungnam; James, Tony D.; Yoon, Juyoung
- Ewha Authors
- 윤주영; K.M.K Swamy
- SCOPUS Author ID
- Issue Date
- Journal Title
- CHEMICAL COMMUNICATIONS
- CHEMICAL COMMUNICATIONS vol. 54, no. 94, pp. 13264 - 13267
- ROYAL SOC CHEMISTRY
- SCI; SCIE; SCOPUS
- Document Type
- 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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