Abstract
Novel heterocyclic azomethine dyes were prepared by the reaction of anthracene-9-carbaldehyde with different heterocyclic amines under microwave irradiation. Structures of the azomethine dyes were confirmed by the elemental analysis, mass spectrometry and several spectroscopic techniques. We studied absorbance and fluorescence spectra of the azomethine dyes in various solvents. They are found to be good absorbers and emitters. We also report photophysical properties like, extinction coefficient, oscillator strength, stokes shift and transition dipole moment. This reflects physicochemical behaviors of synthesized dyes. In addition, their intramolecular charge transfer and nonlinear optical properties, supported by natural bond orbital technique, were also studied computationally by density functional theory. The negative nonlinear refractive index and nonlinear absorption coefficient were measured for these dyes using the closed and open aperture Z-scan technique with a continuous wave helium-neon laser. These are found to vary linearly with solution concentration.
Highlights
Azomethine (-CH = N) linkages heterocyclic compounds are one of most important compounds in all branches of chemistry such as organic, inorganic, medicinal and material chemistry [1]
The newly synthesized azomethine dyes are stable in solution as well as solids
The concentration dependent nonlinear refractive index, nonlinear absorption and third order susceptibility were studied for the novel dyes A1, A2 and A3
Summary
Azomethine (-CH = N) linkages heterocyclic compounds are one of most important compounds in all branches of chemistry such as organic, inorganic, medicinal and material chemistry [1]. They are generally synthesized by the reaction of aromatic aldehydes and aromatic amines [2]. Azomethine compounds are used as intermediate for the various heterocyclic organic syntheses [3]. They are appropriate in the field of coordination chemistry, forming stable complex with different transition metal [4]. In the PLOS ONE | DOI:10.1371/journal.pone.0161613 September 15, 2016
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