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 (n-butoxyloxycarbonyl) perylene (probe 1) and 1-hydroxyl-mono-five-membered S-heterocyclic annulated tetra (n-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 HPO₄²⁻) 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.