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 (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.