Experimental and theoretical study of urea and thiourea based new colorimetric chemosensor for fluoride and acetate
Eramoni Saikia1, Manash Protim Borpuzari1, Bolin Chetia1
1Department of Chemistry, Dibrugarh University, Dibrugarh 786004, Assam, India.
Abstract:
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.
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