Ratiometric fluorescence sensing of fluoride ions by an asymmetric bidentate receptor containing a boronic acid and imidazolium group

Zhaochao Xu, Sook Kyung Kim, Su Jung Han, Chongmok Lee, Gabriele Kociok-Kohn, Tony D. James, Juyoung Yoon

Research output: Contribution to journalArticlepeer-review

142 Scopus citations

Abstract

The synthesis of the first examples of aoion receptors that utilize boron-fluoride interactions and (C-H)+-F∼-t:ype ionic hydrogen-bond interactions in. the binding of F ions is reported herein, o-, m-, and p-Phenylboronic acids were linked to naphthoimidazolium through a methylene group. On the basis of fluorescence and 19F NMR studies, we have confirmed that the addition of fluoride to a boron center occurs prior to the formation of (C-H)+-F∼-type ionic hydrogen bond with the imidazolium moiety. More importantly, these investigations have demonstrated that only the receptor bearing the oriho-directed. boron and imidazolium. exhibits enhanced fluoride binding. The increased binding ability of the asymmetric bidentate receptor of ortho-boronic acid, and imidazolium towards F- enables it to sense fluoride ions in a 95:5 CH3CN/HEPES aqueous solution. The fluorescence responses to different anions were also explored; the orfho-boron-imidazolium receptor displayed ratiometric fluorescence changes and a high selectivity towards fluoride ions over other anions (Cl-, Br-, CH3CO2-, HSO4 - and H2PO4-).

Original languageEnglish
Pages (from-to)3058-3065
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number18
DOIs
StatePublished - Jun 2009

Keywords

  • Anions
  • Boron
  • Fluorescence
  • Fluorides
  • Heterocyeles

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