A naphthoimidazolium-cholesterol derivative as a ratiometric fluorescence based chemosensor for the chiral recognition of carboxylates. Issue 94 (9th November 2018)

• Record Type: Journal Article
• Authors: 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
• Is Part Of: Chemical communications. Volume 54:Issue 94(2018)
• Page Start: 13264
• Page End: 13267
• Publication Date: 2018-11-09
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c8cc06262e
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : We report a naphthoimidazolium-cholesterol derivative (NI-chol 1 ) as a fluorescence based chemosensor for chiral recognition via imidazolium (C–H) + –anion binding. 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.