Physicochemical Investigation of HDDP Azomethine Dye as Turn-On Fluorescent Chemosensor for High Selectivity and Sensitivity of Al3+ Ions

摘要

4-[(2-Hydroxy-naphthalen-1-ylmethylene)-amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (HDDP) was synthesized by the reaction of 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one with 2-hydroxy-l-naphthaldehyde. The structure was confirmed by the IR, H-1-NMR, C-13-NMR, and EI-MS spectra and elemental analysis. Physicochemical parameters of the HDDP such as extinction coefficient, oscillator strength, transition dipole moment, Stokes shift, and fluorescence quantum yield in different solvents were studied on the basis of polarities. The interactions of various metal ions with HDDP were also studied using steady state fluorescence measurements. The emission profile reveals that it acts as off-on type fluorescent chemosensor for selective and sensitive detection of Al3+ ions. Complexation stoichiometry and mechanism of enhancement were determined from a Benesi-Hildebrand plot.