A naphthoimidazolium-cholesterol derivative as a ratiometric fluorescence based chemosensor for the chiral recognition of carboxylates
| Autor: | Gyeongju Ko, Songyi Lee, Juyoung Yoon, Dayoung Lee, Xin Zhang, Yifan Liu, Meng Li, Sungnam Park, Joonyoung F. Joung, Tony D. James, K.M.K. Swamy, Yerin Jeong |
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| Rok vydání: | 2018 |
| Předmět: |
Fluorophore
Proton 010405 organic chemistry Hydrogen bond Metals and Alloys Ionic bonding General Chemistry 010402 general chemistry Photochemistry 01 natural sciences Fluorescence Catalysis 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials chemistry.chemical_compound chemistry Materials Chemistry Ceramics and Composites Moiety Carboxylate Derivative (chemistry) |
| Zdroj: | Chemical communications (Cambridge, England). 54(94) |
| ISSN: | 1364-548X |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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