A naphthoimidazolium-cholesterol derivative as a ratiometric fluorescence based chemosensor for the chiral recognition of carboxylates
- 주제(기타) Chemistry, Multidisciplinary
- 설명문(일반) [Zhang, Xin] Hebei Normal Univ, Coll Chem & Mat Sci, Natl Demonstrat Ctr Expt Chem Educ, Shijiazhuang 050024, Hebei, Peoples R China; [Ko, Gyeongju; Jeong, Yerin; Swamy, K. M. K.; Lee, Dayoung; Liu, Yifan; Yoon, Juyoung] Ewha Womans Univ, Dept Chem & Nano Sci, Seoul 03760, South Korea; [Joung, Joonyoung F.; Park, Sungnam] Korea Univ, Dept Chem, Seoul 02841, South Korea; [Li, Meng; James, Tony D.] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England; [Li, Meng] North China Elect Power Univ, Dept Environm Sci & Technol, 689 Huadian Rd, Baoding 071003, Peoples R China; [Lee, Songyi] Pukyong Natl Univ, Dept Chem, Busan 48513, South Korea
- 등재 SCIE, SCOPUS
- 발행기관 ROYAL SOC CHEMISTRY
- 발행년도 2018
- URI http://www.dcollection.net/handler/ewha/000000155983
- 본문언어 영어
- Published As http://dx.doi.org/10.1039/c8cc06262e
초록/요약
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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