Selective anion receptor for fluoride detection using ferrocenyl–boronate derivative

•Novel ferrocenyl–boronate receptor was synthesized and characterized.•The selective anion sensing property of receptor 1 was studied.•Receptor 1 had high selectivity for F− ion in UV, CV and 1H NMR titrations.

The reaction of ferrocenecarboxaldehyde with (2-aminoethoxy)diphenylborane led to the formation of ferrocenyl-substituted boronate receptor 1, which was characterized by IR, MS, HRMS, 11B, 1H and 13C NMR spectra. The signaling process was confirmed by UV–vis, electrochemistry measurements as well as 1H and 19F NMR spectroscopy. The receptor 1 exhibited high selectivity for F− in CH3CN solution over all the other anions in the DPVs (differential pulse voltammetry). 1H NMR titrations indicated that F− ion induced tautomerism of E- and Z-isomer transformations of the receptor 1 and there were three kinds of protons showing obvious highfield shifts for receptor 1 in DMSO-d6. UV–vis titrations demonstrated that the receptor 1 could bind F− ion forming 1:1 stoichiometric complexes and show high selectivity and sensitivity towards F− ion.

Graphical abstractThe ferrocenyl-substituted boronate receptor 1 showed high selectivity and sensitivity for fluoride anion with optical, electrochemical and 1H NMR changes.Figure optionsDownload full-size imageDownload as PowerPoint slide