Green-synthesis, characterization, photostability and polarity studies of novel schiff base dyes using spectroscopic methods

Abstract

Preparation, characterization, photostability and polarity studies of novel Schiff base dyes using spectroscopic methods were achieved. The Schiff base dyes were prepared by the reaction of salicylaldehyde/2-Hydroxy-1-naphthaldehyde with aminophenazone under microwave irradiation. The spectroscopic (FT-IR, 1H NMR, 13C-NMR, Mass) studies and elemental analyses were in good agreement with chemical structure of synthesized compounds. In addition, UV-Vis and fluorescence spectroscopic experiments showed that these dyes are good absorbent and fluorescent. Based on the photostability study of these dyes, minimal to no loss in fluorescence intensities of 4-[(2-Hydroxy-benzylidene)-amino] 1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (D1) (6.14%) and 4-[(2-Hydroxy-naphthalen-1-ylmethylene)-amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (D2) (2.95%) was observed with an increase in the exposure time using time-based fluorescence steady-state experiments. These studies also inferred that these Schiffbase dyes have a high photostability against photobleaching. In addition, Dye 2 is found to be more sensitive than Dye 1 to the polarity of the microenvironment provided by different solvents based on the results of fluorescence polarity studies.