Experimental and theoretical study of urea and thiourea based new colorimetric chemosensor for fluoride and acetate ions.

Two new anion receptors 1,1-(4-nitro-1,2-phenylene) bis(3-phenylurea) (1) and 1,1-(4-nitro-1,2-phenylene) bis(3-phenylthiourea) (2) have been reported here. The binding and colorimetric sensing properties of receptors 1 and 2 with different anions were investigated by naked-eye, (1)H-NMR and UV-Vis spectroscopy. They showed effective and selective binding with two biologically important anions F(-) and CH3COO(-), in presence of other anions, such as Cl(-), Br(-), I(-), NO2(-), ClO4(-), HSO4(-), H2PO4(-), N3(-), CN(-) in acetonitrile. The relative binding mode of fluoride and acetate anions towards receptors 1 and 2 were studied using density functional theory (DFT), in gas phase and in acetonitrile solvent. Computational studies revealed that receptor 1 formed complexes by two intermolecular hydrogen bonds while receptor 2 by three intermolecular hydrogen bonds. In addition, time dependent DFT (TD-DFT) calculations qualitatively match the experimental UV-Vis spectra.