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 language | English |
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Pages (from-to) | 3058-3065 |
Number of pages | 8 |
Journal | European Journal of Organic Chemistry |
Issue number | 18 |
DOIs | |
State | Published - Jun 2009 |
Keywords
- Anions
- Boron
- Fluorescence
- Fluorides
- Heterocyeles