Experimental and theoretical studies on monoazo dye including diphenylamine and N-methyldiphenylamine derivatives

Abstract

In this manuscript, two series of azo dyes preparing by coupling diphenylamine and N-methyl diphenylamine and diazotized substituted anilines bearing various substituents were designed and synthesized. These azo dyes were characterized by spectroscopic techniques such as 1H/13C NMR and HRMS or LCMS. Photophysical, NLO and protonation properties were investigated by experimentally and theoretically. The absorption maxima were observed in long wavelength in DMSO. The most stable tautomeric form of dyes which have tautomeric forms, were determined using model compounds. The results showed that the azo dyes are stable in azo form in all solvents used. For the usability as optic dye of the synthesized dyes, thermal property of all dyes was also determined. The all compounds are thermally stable and Td values are bigger than 220 °C.