Synthesis, characterization and spectroscopic properties of new azo dyes derived from aniline derivatives based on acetylacetone and azo-metal (II) complexes and singular value decomposition (SVD) investigation

Noroozi Pesyan, Nader; Gholsanamloo, Vali; Moradi Par, Maryam; Rashidnejad, Hamid; Gharib, Ali; Nejati, Kamelia

doi:10.30473/icc.2019.3951

Document Type : Original Research Article

Authors

¹ Faculty of Chemistry, Urmia University, 57159, Urmia, Iran

² Faculty of Chemistry, Urmia University, 57159,Urmia, Iran

³ Department of Chemistry, Islamic Azad University, Mashhad, Iran

⁴ Department of Chemistry, Payame Noor University, PO.BOX 19395-3697 Tehran, Iran

https://doi.org/10.30473/icc.2019.3951

Abstract

Four new azo-dyes, 3-phenyl azopentane-2,4-dion (LA), 3-(4-nitro phenyl azo)-pentane-2,4-dion (LP), 3-(2-nitro phenyl azo)-pentane-2,4-dion (LO) and 4-(1-acetyle-2-oxo-propyl azo)-benzene sulfonate sodium (LS), were synthesized from, aniline, 4-nitroaniline, 2-nitroaniline and sulfanilic acid with acetylacetone, respectively. Reaction of these new dyes with acetate salts of copper(II), nickel(II) and cobalt(II) in molar ratios of 1:2 were carried out to produce azo metal (II) complexes with the general stoichiometry; CuL2, CoL2 and NiL3 in complexes. Structure of azo dyes was characterized using FT-IR,1H NMR,13C NMR, UV-Visible and also the corresponding metal (II) complex were characterized by FT IR, UV-Visible and CHN and XRD analysis techniques. Elemental analysis and spectral data indicated that the dye as a ligand with two teeth, N and O, acts as a bidentate ligand. Differences in absorption maxima of azo ligands compared to those corresponding complexes were also studied. Also, in this work, singular value decomposition (SVD) as a chemometric method was used to determine the Cu(II), Co(II) and Ni(II) complexes with the mentioned ligands in methanol by UV-Vis spectrophotometry. SVD method confirmed the formation of CuL2, CoL2 and NiL3 complexes.

Graphical Abstract

Keywords

Main Subjects

Organic chemistry

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Iranian chemical communication

Synthesis, characterization and spectroscopic properties of new azo dyes derived from aniline derivatives based on acetylacetone and azo-metal (II) complexes and singular value decomposition (SVD) investigation

References

References

Volume 7, Issue 1, pp. 1-89, Serial No. 22
January 2019
Pages 71-89

Synthesis, characterization and spectroscopic properties of new azo dyes derived from aniline derivatives based on acetylacetone and azo-metal (II) complexes and singular value decomposition (SVD) investigation

References

References

Volume 7, Issue 1, pp. 1-89, Serial No. 22January 2019Pages 71-89

Volume 7, Issue 1, pp. 1-89, Serial No. 22
January 2019
Pages 71-89