Synthesis and Photophysical Behaviours of Novel Phenanthro[9,10-d] imidazole Substituted Azo Dyes in Solvent Media

Abstract

In this study, three novel phenanthroimidazole derivatives containing azo group were synthesized and their photophysical properties were investigated. For this purpose, 2-(4-nitrophenyl)1H-phenanthro[9,10-d]imidazole structure obtained from 9,10-phenanthroquinone and 4-nitrobenzaldehyde was reduced with palladium on activated charcoal 10 % and hydrazine hydrate. Phenanthro[9,10-d]imidazole-2-yl)aniline obtained in this way was converted to phenantroimidazole-azo derivatives containing different aromatic groups. Structural analyses were performed by FT-IR, NMR, LC-MS spectroscopic techniques. Spectral characterizations and photostability studies of phenanthroimidazole derivatives were performed by UV-vis and fluorescence spectroscopy in solvent media. The maximum absorption and emission wavelengths, molar extinction coefficients, singlet energy levels, Stokes’ shift values of phenanthroimidazole-azo derivatives were obtained.