Determination of dipole moment, solvatochromic studies and application as turn off fluorescence chemosensor of new 3-(4-(dimethylamino)phenyl)-1-(5-methyl-1-(naphthalen-1-yl)-1H-1,2,3-triazol-4-yl)prop-2-en-1-one

Abstract

A novel compound 3-(4-(dimethylamino)phenyl)-1-(5-methyl-1-(naphthalen-1-yl)-1H-1,2,3-triazol-4-yl)prop-2-en-1-one with intramolecular charge transfer characteristics was synthesized and characterized by 1H NMR, 13C NMR and X-ray crystallography. The ground state dipole moment and excited state dipole moment were estimated from solvatochromic methods using Bilot–Kawski, Lippert–Mataga, Bakhshiev's, Kawski–Chamma–Viallet and Reichardts correlations. The excited state dipole moment was found higher than ground state of molecule. Solute–solvent interactions were studied using multi-parameter solvent polarity scales proposed by Kamlet–Taft and Catalan. Effect of various metal ions on fluorescent behavior was also studied. It acts as a selective, sensitive and reversible fluorescent chemosensor for micromolar detection of Fe+3 ions. The linear range for this chemosensor was found to be 1×10−7 to 1×10−5mol/L with detection limit of 42μM. Binding stoichiometry and mechanism of Fe+3 ion detection was also investigated.