Investigation of The Effects of Diaminopyridine and o-Vanillin Derivative Schiff Base Complexes of Mn(II), Mn(III), Co(II) and Zn(II) Metals on The Oxidative Bleaching Performance of H2O2

Catalytic applications are widely used in both industrial and individual applications today due to their many advantages, especially the energy and time they provide. For this purpose, many coordination compounds have been synthesized and their catalytic performances have been investigated in recent years. In this study, the Schiff base ligand, (N,N’-bis(2-hydroxy-3-methoxyphenylmethylidene)-2,6-pyridinediamine, BHMP), was synthesized with 2,6-diaminopyridine with o-vanillin. Mn(II), Mn(III), Co(II), Zn(II) complexes were obtained with the synthesized ligand. Spectroscopic methods such as FT-IR, 1H-NMR, UV-vis, Mass, and melting point determination methods were used for the structure elucidation of the synthesized compounds. The performances of the obtained complexes as bleach catalysts, which is an important application area of Schiff base complexes, were investigated. According to the bleaching measurement results; the highest catalytic effect on the bleaching performance of H2O2 in pH 10.5 buffer at 25°C under homogeneous conditions was obtained with Co(II) complex, and it was understood that this complex was followed by Mn(II), Mn(III) and Zn(II) complexes, respectively

PDF

___

[1] A.Sakthivel, K.Jeyasubramanian, B. Thangagiri and J. Dhaveethu, “Recent advances in schiff base metal complexes derived from 4-aminoantipyrine derivatives and their potential applications” Journal of Molecular Structure, vol. 1222, 128885, 2020.

[2] B. Naureen, G.A.Miana, K. Shahid, M. Asghar, S. Tanveer and A. Sarwar, “Iron (III) and zinc (II) monodentate Schiff base metal complexes: Synthesis, characterisation and biological activities” Journal of Molecular Structure, vol. 1231, 129946, 2021.

[3] N. Beyazit, D. Çakmak and C. Demetgül, “Chromone-based Schiff base metal complexes as catalysts for catechol oxidation: Synthesis, kinetics and electrochemical studies” Tetrahedron, vol. 73, no. 19, pp 2774-2779, 2017

[4] S. Sengupta, S. Khan, B. N. Mongal, W.Lewis, M. Fleck, S. K. Chattopadhyay and S. Naskar, “Electrocatalytic hydrogen production and carbon dioxide conversion by earth abundant transition metal complexes of the Schiff base ligand: (E)-1-((2-dimethylamino)-propylimino) methyl)naphthalene-2-ol” Polyhedron, vol. 191, Article ID 114798, 2020.

[5] A. A. Alshaheri, M. I. M. Tahir, M. B. A. Rahman, T. B. S. A.Ravoof and T. A. Saleh, “Catalytic oxidation of cyclohexane using transition metal complexes of dithiocarbazate Schiff base” Chemical Engineering Journal, vol. 327, pp. 423-430, 2017.

[6] B. Tamami and S. Ghasemi, “Catalytic activity of Schiff-base transition metal complexes supported on crosslinked polyacrylamides for hydrogen peroxide decomposition” Journal of Organometallic Chemistry, vol. 794, pp. 311-317, 2015.

[7] S. Annapoorani and C. Krishnan, “Synthesis and spectroscopic studies of trinuclear N4 Schiff base complexes” International Journal of Chem Tech Research, vol. 5, no. 6, pp.180–185, 2013.

[8] H. I. Ugras, I. Basaran, T. Kilic and U. Cakir, “Synthesis, complexation and antifungal, antibacterial activity studies of a new macrocyclic schiff base” Journal of Heterocyclic Chemistry, vol. 43, no. 6. pp.1679-1684, 2006.

[9] L. Shi, H-M. Ge, Shu-H. Tan, H-Q. Li, Yong-C. Song and H-L. Zhu, “Synthesis and antimicrobial activities of Schiff bases derived from 5-chloro-salicylaldehyde” European Journal of Medicinal Chemistry, vol. 42, no. 4, pp. 558-564, 2007.

[10] A. A. Osowole, A. C. Ekennia and B. O. Achugbu, “Synthesis, Spectroscopic Characterization and Antibacterial Properties of some Metal (II) Complexes of 2-(6-methoxybenzothiazol-2-ylimino) methyl)-4-nitrophenol” Research and Reviews: Journal of Pharmaceutical Analysis, vol. 2, no. 2, pp. 1-5, 2013.

[11] S. M. Morgan, A. Z. El‐Sonbati and H. R. Eissa, “Geometrical structures, thermal properties and spectroscopic studies of Schiff base complexes: Correlation between ionic radius of metal complexes and DNA binding” Journal of Molecular Liquids, vol. 240, pp. 752-776, 2017.

[12] T. Mangamamba, M. C. Ganorkar and G. Swarnabala, “Characterization of Complexes Synthesized Using Schiff Base Ligands and Their Screening for Toxicity Two Fungal and One Bacterial Species on Rice Pathogens” International Journal of Inorganic Chemistry, Article ID 736538, 2014.

[13] T. Wieprecht, M. Hazenkamp, H. Rohwer, G. Schlingloff and J. Xia, 2007. “Design and application of transition metal catalysts for laundry bleach” Comptes Rendus Chimie, vol. 10, no.4-5, pp. 326-340, 2007.

[14] R. Hage, J.W. de Boer, F. Gaulard and K. Maaijen, “Chapter There-Manganese and ıron bleaching and oxidation catalysts”, Advances in Inorganic Chemistry, vol. 65, pp. 85-116, 2013.

[15] W. Woods, “Bleaching compositions and methods” U.S. Patent, no. 3532634, 1970.

[16] T.D. Finch and R. J. Wilde, “Oxygen bleaching systems in domestic laundry” European Patent, no. 141470, 1984.

[17] H. A. H. Alshamsi and A. K. A. H. Shdood, “Uv-ClO2 Assisted decolorization of methylene blue”, Journal of Chemical and Pharmaceutical Research, vol. 7, no. 9, pp. 36- 44, 2015.

[18] L. Simandi, “Catalysis by metal complexes” Kluwer Academic, Dordrecht, pp. 13, 1992.

[19] H. Korpi, P. Lahtinen, V. Sippola, O. Krause, M. Leskela, and T. Rep, “An efficient method to investigate metal-ligand combinations for oxygen bleaching” Applied Catalysis A. General vol. 268, pp. 199-206, 2004.

[20] P. Sen, D. Kara Simsek and S. Z. Yildiz, “Functional zinc(II) phthalocyanines bearing Schiff base complexes as oxidation catalysts for bleaching systems” Applied Organometalllic Chemistry, vol. 29, no. 8, pp. 509–516, 2015.

[21] H. Sakallıoğlu, “Manyetik Nanopartiküller Üzerine Desteklenmiş Schiff Bazı Türevi Metal Komplekslerinin Sentezleri ve Katalitik Etkinliklerinin İncelenmesi” Çukurova University, Institute of Science, Department of Chemistry, Master Thesis, 2013.

[22] K.C.Gupta and A. K. Sutar, “Catalytic activities of Schiff base transition metal complexes” Coordination Chemistry Reviews vol. 252, no. pp. 1420-1450, 2008.

[23] P. Sen, E. Yildirim and S. Z. Yildiz, “New alkaline media-soluble functional zinc(II) phthalocyanines bearing poly (hydroxylmethyl)iminomethane Schiff base complexes in catalytic bleaching” Synthetic Metals, vol. 215, pp. 41-49, 2016.

[24] K.C. Gupta, A.K. Sutar and C-C. Lin, “Polymer-supported Schiff base complexes in oxidation reactions” Coordination Chemistry Reviews, vol. 253, no. 13–14, pp. 1926-1946, 2009.

[25] A. M. Abu-Dief and I. M. A. Mohamed, “A review on versatile applications of transition metal complexes incorporating Schiff bases” Beni-Suef University Journal of Basic and Applied Sciences, vol. 4, no.2, pp. 119-133, 2015.

[26] S. J. McNeil, M. R. Sunderland and S. J. Leighs, “The utilisation of wool as a catalyst and as a support for catalysts” Applied Catalysis A: General, vol. 541, pp. 120-140, 2017.

[27] W. T. Eckenhoff, “Molecular catalysts of Co, Ni, Fe, and Mo for hydrogen generation in artificial photosynthetic systems” Coordination Chemistry Reviews, vol. 373, pp. 295-316, 2018.

[28] X. Li, C-H. Li, J-H. Jiang, et al. “Synthesis and microcalorimetric determination of the bioactivities of a new Schiff base and its bismuth(III) complex derived from o-vanillin and 2,6-pyridinediamine” Journal of Thermal Analysis and Calorimetry vol. 127, pp. 1767–1776, 2017.

[29] N. Galic´, Z. Cimerman, V. Tomisic, “Spectrometric study of tautomeric and protonation equilibria of o-vanillin Schiff base derivatives and their complexes with Cu(II)” Spectrochim Acta, Part A.,vol. 71, pp.1274–80, 2008.

[30] X. Li, J-H. Jiang, Q. Chen, at al. “Synthesis of nordihydroguaiaretic acid derivatives and their bioactivities on S. pombe and K562 cell lines” European Journal of Medicinal Chemistry, vol. 62, pp. 605-613, 2013.

[31] R. Hage and A. Lienke, “Applications of transition-metal catalysts to textile andwood-pulp bleaching” Angewandte Chemie Int. Ed., vol. 45, no. 2, pp. 206–222, 2005.

[32] P. Sen, S.Z. Yildiz, N. Dege, M. Atakay, B. Salih, “Functional Substituted Phthalocyanines Bearing Ter-pyridine Complexes as Macromolecular Oxidation Catalysts for Bleaching Systems” ChemistrySelect, vol.2, no. 9, pp. 2643 -2650, 2017.

[33] P. Sen, D. Akagunduz, A. S. Aghdam, F. Ç. Cebeci, T. Nyokong and T. Catal, “Synthesis of Novel Schiff Base Cobalt (II) and Iron (III) Complexes as Cathode Catalysts for Microbial Fuel Cell Applications” Journal of Inorganic and Organometallic Polymers and Materials, vol. 30, pp.1110–1120, 2020.

[34] İ. Gönül, E. Fakı, B. Ay, M. Köse and S. Serin, “Cobalt(II), nickel(II) and copper(II) complexes of a Schiff base ligand: synthesis, structural characterization and luminescence properties” Transition Metal Chemistry, vol. 43, pp. 73–81, 2018.

[35] I. A. Gegen, “Detection of Methoxyl Group by Infrared Spectrocopy” Applied Spectrocopy, vol. 22, no. 3, pp. 164166, 1968.

[36] R. K. Shan, K. S. Abou-Melha, F. A. Saad, et al., “Elaborated studies on nano-sized homo-binuclear Mn(II), Fe(III), Co(II), Ni(II), and Cu(II) complexes derived from N2O2 Schiff base, thermal, molecular modeling, drug-likeness, and spectral” Journal of Thermal Analysis and Calorimetry, vol. 123, pp. 731–743, 2016.

[37] N. K. Ngan, K. M. Lo and C. S. R. Wong, “Synthesis, structure studies and electrochemistry of molybdenum(VI) Schiff base complexes in the presence of different donor solvent molecules” Polyhedron, vol 30, pp. 2922-2932, 2011.

[38] R. N. Egekenze, Y. Gultneh and R. Butcher, “Mn(III) and Mn(II) complexes of tridentate Schiff base ligands; synthesis, characterization, structure, electrochemistry and catalytic activity” Inorganica Chimica Acta, vol. 478, pp. 232–242, 2018.

[39] P. Sen, S. Z. Yildiz, “The investigation of oxidative bleaching performance of peripherally Schiff base substituted tri-nuclear cobalt-phthalocyanine complexes” Inorganica Chimica Acta, vol. 462, pp. 30-39, 2017.

[40] P. Sen, N. Dege and S.Z. Yildiz, “Tri-nuclear phthalocyanine complexes carrying N/O donor ligands as hydrogen peroxide catalysts, and their bleaching activity measurements by an online spectrophotometric method” Journal of Coordination Chemistry, vol. 70, no.16, pp. 2751-2770, 2017.

[41] P. Sen and S. Z. Yildiz, “Substituted manganese phthalocyanines as bleach catalysts: synthesis, characterization and the investigation of de-aggregation behavior with LiCl in solutions” Research on Chemical Intermediates, vol. 45, pp. 687–707, 2019.