Synthesis, Characterisation and DFT Calculations of Azo-Imine Dyes

Abstract

In this study, azo dyes containing an imine group were synthesised by coupling phydroxybenzylidene aniline with the diazonium salts of p-toluidine, 4-aminophenol, aniline, pchloroaniline, p-fluoroaniline and p-nitroaniline. The compounds were characterised by melting point, elemental, UV-Vis and IR analyses as well as 1 H-NMR and 13 C-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.

HJSE19030000101Synthesis, Structural Characterization AndTheoretical Investigations of New Azo-Azomethine Compounds Bearing Acryloyl MoietySevil

“…The -OH strecthing peak of the compounds 3 were observed at 3584-3180 cm -1 as a broad peak in agreement with the literature [6,22,26] and the theoretical value which appeared in the range of 3812 cm -1 (according to cc-pvtz basis set) and 3832 cm -1 (according to 6-311++g(2d,2p) basis set). The characteristic strecthing peaks of the azo group -N=N-are observed in the range of 1400-1550 cm -1 as a medium band in the literature [2,4,26,27]. In our study -N=N-strecthing peaks of the compounds (2-6) are observed at 1407-1442 cm -1 and 1513 -1548 cm -1 experimentally and calculated as 1496-1547cm -1 (according to cc-pvtz basis set) and 1478-1543 cm -1 (according to 6-311++g(2d,2p) basis set.…”

“…The theoretical and experimental IR spectral data are given in Table 4. The aromatic =C-H strecthing peaks appear in the range of 3000-3100 cm -1 [2,26,27]. The aromatic =C-H strecthing peaks were observed at 3046-3134 cm -1 which are in good agreement with the calculated frequencies such as 3148-3201 cm -1 (according to cc-pvtz basis set) and 3154-3199 cm -1 (according to 6-311++g(2d,2p basis set).…”

“…Azo-azomethine derivatives (1) were synthesized by the coupling reaction with E-4-((phenylimino)methyl)phenol [25,26] and diazonium salts as described in the literature method [8,9,22,26].…”

A Novel Conjugated Pyrene-BODIPY Dyad: Synthesis, Characterization and Properties

“…The optical and electrochemical properties of the new molecule were examined by UV-Vis absorption, fluorescence emission spectroscopies, and CV. Also, the photophysical and electrochemical properties of the molecule were studied by DFT program to calculate the photophysical and electrochemical parameters (28)(29)(30).…”

Synthesis, Characterization, and Theoretical Calculation of New Azo Dyes Derived from [1,5‐a]Pyrimidine‐5‐one Having Solvatochromic Properties

“…Azo dyes are well-known compounds for giving color to various textile materials for many years [1][2][3][4]. These dyes play also a major role in industrial products such as printing, leather, papermaking, food industries, and drug design, except for textile dyeing [5,6].…”