Synthesis, Characterisation and DFT Calculations of Azo-Imine Dyes

Year 2018, Volume: 5 Issue: 1, 159 - 178, 01.09.2017

Sevil Özkınalı , Muhammet Serdar Çavuş , Büşra Umur Sakin

https://doi.org/10.18596/jotcsa.346278

Cited By: 4

Abstract

In this study, azo dyes containing an imine group were synthesised by coupling
p-hydroxybenzylidene aniline with the diazonium salts of p-toluidine,
4-aminophenol, aniline, p-chloroaniline,
p-fluoroaniline and p-nitroaniline.
The compounds were characterised by melting point, elemental, UV-Vis and IR analyses as well as
¹H-NMR and ¹³C-NMR spectroscopies. Moreover, the
experimental data were supplemented with density functional theory (DFT) calculations. The experimental data on FT-IR and UV–Vis spectra of
the compounds were compared with theoretical results. The DFT calculations were performed to obtain the ground
state geometries of the compounds using the B3LYP hybrid functional level with 6-311++g(2d,2p)
basis set. Frontier molecular orbital energies, band gap energies and some chemical reactivity
parameters, such as chemical hardness and electronegativity, were calculated and compared with experimental values. A significant correlation was observed between the
dipole moment and polarities of the solvents and the absorption wavelength of
the compounds. 

Keywords

Azo-imine, Schiff Bases, DFT

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