Synthesis and Preliminary Characterization of Metal Complexes of 1, 2-Dihydroxyanthraquinone-Based Azo Compound.
Resumen
This paper reports the preliminary characterization of six transition metal complexes of an azo compound derived from the well-established coupling reaction between the diazonium salt of the substituted aromatic amine: 2aminobenzoic acid and the coupler, 1, 2-dihydroxyanthraquinone.The products yield was between 75% - 85%. The resultant metal complexes were preliminarily characterized using melting point, Solubility, Chromatography, Ultraviolet –Visible (UV-Vis) and Infrared (IR) spectroscopy. Well defined melting points for the azo metal complexes gave ranges between: 298oC-309oC. The retardation factor (R) values for these complexes ranged f between: 0.59-0.72. The bathochromic shifts for the various metal complexes in the visible region of the electromagnetic spectra ranged between 422 nm to 466 nm and 484 nm to 604 nm. The M-O and M-N vibrations in the infrared spectra at 410-495 cm-1 and 540-591 cm-1 respectively provide evidence of the formation of metal complexes. These new azo metal complexes with anthraquinone moiety has potential application as pigments in surface coatings and in textile printing due to their insolubility in water and most organic solvents in addition to their thermal stability.
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Referencias
Abbas, R. A., & Alias, F. M. (2015). Synthesis and properties of some metal complexes of azo compounds. International Journal of Science and Research (IJSR), 4(8), 85-92.
Abdallah, S. M. (2010). Metal complexes of azo compounds derived from 4-acetamidophenol and substituted aniline. Arabian Journal of Chemistry, 5, 251-256.
Akaranta, O., & Odozi, T. O. (1985). Azo metal complexes from red onion skin (Allium cepa) tannin extract condensation products. Journal of Leather Research, 3(4), 82-85.
Bedea, M., Olar, R., Cristurean, E., Marinescus, D., Emandi, A., Budrugeae, P., & Segal, E. (2004). Thermal stability study of some azo derivatives and their complexes. Part 2. New azo derivative pigments and their Cu complexes. Journal of Analytical Color, 77(3), 815-824.
Hamilton-Amachree, A., & Adiukwu, P. U. (2015). Synthesis and dyeing properties of phenyl azo moieties of 1,2-dihydroxyanthraquinone. International Journal of Basic Science and Technology, 1(1), 7-10.
Hitoshi, U. (2004). National Textile Center. Annual report project CO3PH01.
Kirkan, B., & Gup, R. (2008). Synthesis and dyeing performance of some disperse azo dyes. Journal of Serbian Chemical Society, 12(6), 710-714.
Kirk-Othmer. (1992). Chemistry of azo dyes. In Encyclopedia of Chemical Technology (4th ed., Vol. 3, pp. 821-852).
Koh, J., & Greaves, A. J. (2001). Synthesis and application of an alkali-clearable azo disperse dye containing a fluorosulfonyl group and analysis of its alkali hydrolysis kinetics. Dyes and Pigments, 50(2), 117-126.
Lu, L., He, L., Zhang, S., & Freeman, H. S. (2012). Novel yellow azo-anthraquinone dyes for polylactide fibers: Effect of alkyl chain length. Coloration Technology, 128(2), 121-126. Von Blackwell Publishing Ltd.
Masoud, S. M., Khali, E. A., Hindaway, E. A., & Mohamed, E. F. (2004). Spectroscopic studies of some azo compounds and their cobalt, copper and nickel complexes. Spectrochimica Acta Part A, 60, 2807-2817.
Mohamed, G. G., El-Gamel, N. E. A., & Teixidor, F. (2001a). Complexes of 2-(2-benzimidazolylazo)-4-acetamidophenol, phenoldiazenyl-containing ligand. Polyhedron, 20(21), 2689-2696.
Nishihara, H. (2004). Multi mode molecular switching properties and functions of azo-conjugated metal complexes. Bulletin of the Chemical Society of Japan, 77, 407-428.
Okah, P. K. (2014). Synthesis and application of azo dyes on polylactide fabrics. M.Sc. Thesis, ABU, Zaria, Nigeria.
Otutu, J. O., Okoro, D., & Ossai, E. K. (2008). Preparation of dis-azo dyes from o-aminophenol and their fastness properties on synthetic polymer fibers. Journal of Applied Science, 8(2), 334-339.
Patel, V. K., Prajapati, N. K., & Patel, D. G. (2013). Synthesis, characterization and spectral studies of chelating azo dyes containing salicylic acid ligands. Pelagia Research Library, Der Chemica Sinica, 4(4), 70-72.
Sekar, N., & Mahajan, S. S. (2007). Synthesis and application of anthraquinone azo dyes in colourage. 54(1), 64-71.
Shahinian, E. G., Haiduc, I., & Sebe, I. (2011). Synthesis and characterization of new azo coumarin dyes. U.P.B. Scientific Bulletin, Series B, 73(4). ISSN 1454-2331.
Soliman, E. M., & El-Shababy, M. (1994). Synthesis, characterization and electrical conductivity properties of homo- and trimetallic complexes of mixed azo dyes. Journal of Materials Science, 29, 4505-4509.
Warring, D. R., & Hallas, G. (1990). The chemistry and application of dyes. Plenum Press, New York and London.
Zollinger, H. (1987). Color chemistry: Synthesis, properties and applications of organic dyes. VCH, Weinheim.
Zollinger, H. (1991). Color chemistry: Synthesis, properties and application of organic dyes and pigments (2nd ed.). VCH, Weinheim; New York.
Zollinger, H. (1994). Diazo chemistry I. Aromatic and heteroaromatic compounds. VCH, Weinheim; New York. (pp. 19-22).
