Novel fluorescent probes for the fluoride anion based on hydroxy-substituted perylene tetra-(alkoxycarbonyl) derivatives

Abstract

The fluoride anion (F^-) sensing abilities of 1-hydroxyl-3,4,9,10-tetra (<i>n</i>-butoxyloxycarbonyl) perylene (probe 1) and 1-hydroxyl-mono-five-membered <i>S</i>-heterocyclic annulated tetra (<i>n</i>-butoxyloxycarbonyl) perylene (probe 2) were studied through visual detection experiments, UV-Vis, fluorescence, and ¹H NMR titrations. The probes were sensitive and selective for distinguishing F^- from other anions (Cl^-, Br^-, I^-, SO₄ ^-, PF₆ ^-, H₂PO₄ ^-, BF₄ ^-, ClO₄ ^-, OH^-, CH₃COO^-, and HPO₄ ^2-) through a change of UV-Vis and fluorescence spectra. The absorption and fluorescence emission properties of the probes arise from the intermolecular proton transfer (IPT) process between a hydrogen atom on the phenolic O position of probe and the F^- anion. The sensing mechanism was supported by theoretical investigation. Moreover, probe-based test strips can conveniently detect F^- without any additional equipment, and they can be used as fluorescent probes for monitoring F^- in living cells.