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

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 (1)H NMR titrations. The probes were sensitive and selective for distinguishing F(−) from other anions (Cl(−), Br(−), I(−), SO(4)(−), PF(6)(−), H(2)PO(4)(−), BF(4)(−), ClO(4)(−), OH(−), CH(3)COO(−), and HPO(4)(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.