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

Xin Zhang, Gyeongju Ko, Joonyoung F. Joung, Meng Li, Yerin Jeong, K. M.K. Swamy, Dayoung Lee, Yifan Liu, Songyi Lee, Sungnam Park, Tony D. James, Juyoung Yoon

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6 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)13264-13267
Number of pages4
JournalChemical communications (Cambridge, England)
Volume54
Issue number94
Early online date2 Nov 2018
DOIs
Publication statusPublished - 22 Nov 2018

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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