Synthesis, characterization and investigation of the spectroscopic properties of novel peripherally 2,3,5-trimethylphenoxy substituted Cu and Co phthalocyanines, the computational and experimental studies of the 4-(2,3,5-trimethylphenoxy)phthalonitrile

Year 2016, Volume: 3 Issue: 3, 683 - 706, 08.01.2017

Nesuhi Akdemir

https://doi.org/10.18596/jotcsa.287303

Cited By: 3

Abstract

4-(2,3,5-trimethylphenoxy)phthalonitrile (3) was firstly prepared via aromatic nucleophilic substitution reaction and characterized by FT-IR, mass spectrometry, ¹H and ¹³C NMR techniques. The molecular structure of the compound (3) was optimized using Density Functional Theory (DFT/B3LYP) method with 6-311G(d,p) basis set in the ground state. The molecular geometric parameters which were obtained by X-ray single crystal diffraction method and the spectral results were compared with computed bond lengths and angles, vibrational frequencies and ¹H, ¹³C NMR chemical shifts values of the compound (3). Also, Cu(II) and Co(II) phthalocyanines were synthesized by the treatment of dinitrile derivative with anhydrous CuCl₂ or CoCl₂ under N₂ atmosphere in dry n-pentanol at 140^oC. The new compounds have been determined by elemental analysis, FT-IR and electronic absorption. The UV-Vis spectra of the Cu(II) and Co(II) phthalocyanines were recorded with different concentration in THF and also with different solvents as DMF, DMSO, DCM, CHCl₃, toluene.

Keywords

Phthalocyanines, phthalonitrile, 2,3,5-trimethylphenol, DFT

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