The synthesis of polymeric s-Triazine schiff bases and investigation of [(Fe(III)/Mn(III)(Salen)Cl] metal complexes

Abstract

In this study, 2,4,6-triamino-1,3,5-triazine (melamine) as the starting material. A one-way Schiff base reaction took place with the condensation reaction of melamine and p-hydroxybenzaldehyde. Then, monopodal s-triazine-centered Schiff base ligand complexes were obtained by obtaining a single oxygen-bridged compound of [(Fe(III)/Mn(III)Salen)Cl] ligand complexes, which we synthesized monopodal Schiff base s-triazine monomer by the literature. The obtained unidirectional s-triazine-centered Schiff base ligand complexes were polymerized under reflux with different dialdehyde compounds. Consequently, the structures of the obtained all ligands and complexes were characterized using elemental analysis, FT-IR spectroscopy, 1H-NMR spectroscopy, ESI-LS-MS spectroscopy, TGA-DTA analysis and magnetic susceptibility measurement techniques.

Keywords

• melamine
• Schiff Base
• s-triazine
• Salen
• Polymer Complexes

Polimerik s-Triazin schiff bazlarının sentezi ve [(Fe(III)/Mn(III)(Salen)Cl] metal komplekslerinin incelenmesi

Abstract

Bu çalışmada çıkış maddesi olarak 2,4,6-triamino-1,3,5-triazin (melamin) kullanıldı. Melamin ve p-hidroksibenzaldehitin kondensasyon reaksiyonu ile tek yönlü Schiff baz reaksiyonu gerçekleşti. Daha sonra, monopodal Schiff baz s-triazin monomeri literatüre uygun olarak sentezlenen [(Fe(III)/Mn(III)Salen)Cl] ligand komplekslerini tek oksijen ile köprülü bileşiği elde edilerek monopodal s-triazin merkezli Schiff baz ligand kompleksleri elde edildi. Elde edilen tek yönlü s-triazin merkezli Schiff baz ligand kompleksleri farklı dialdehit bileşikleri geri soğutucu altında polimerleştirildi. Sonuç olarak, elde edilen ligandların, monomerik ve polimerik komplekslerinin yapıları elementel analiz, FT-IR spektroskopisi, 1H-NMR spektroskopisi, TGA-DTA analizi, viskozimetre ve manyetik sussebtibilite ölçüm teknikleri kullanılarak aydınlatıldı.

Keywords

• melamine
• Schiff baz
• s-triazin
• salen
• polimer kompleks

References

1. Arslan, B., (2015), Polimerik Triazin Schiff Bazlarının Sentezi ve Bazı Metal Komplekslerinin İncelenmesi, Yüksek lisans tezi, Selçuk Üniversitesi Fen Bilimleri Enstitüsü,Konya, 55.
2. Arslaner, C., Karakurt, S. and Koc, Z. E., (2017), Synthesis of benzimidazole Schiff base derivatives and cytotoxic effects on colon and cervix cancer cell lines, Biointerface Research in Applied Chemistry, 7 (4), 2103-2107.
3. Celikbilek, S. and Koc, Z. E., (2014), Investigation of Dipodal oxy-Schiff base and its salen and salophen Fe(III)/Cr(III)/Mn(III) Schiff bases (N2O2) caped complexes and their magnetic and thermal behaviors, Journal of Molecular Structure, 1065, 205-209.
4. Gembicky, M., Boca, R. and Renz, F., (2000), A heptanuclear Fe(II)-Fe(III)(6) system with twelve unpaired electrons, Inorganic Chemistry Communications, 3 (11), 662-665.
5. Karipcin, F. and Karatas, I., (2001), The synthesis of substituted bis(aminophenylglyoxime)methanes and their polymeric metal complexes with Cu(II), Ni(II), and Co(II) salts, Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 31 (10), 1817-1829.
6. Koc, Z. E. and Ucan, H. I., (2007), Complexes of iron(III) salen and saloph Schiff bases with bridging 2,4,6-tris(2,5dicarboxyphenylimino-4-formylphenoxy)-1,3,5-triazine and 2,4,6-tris(4-carboxyphenylimino-4'-formylphenoxy)-1,3,5-triazine, Transition Metal Chemistry, 32 (5), 597-602.
7. Koc, Z. E. and Ucan, H. I., (2008), Complexes of Iron(III) and Chrom(III) Salen and Saloph Schiff Bases with Bridging 2,4,6-tris(4-nitrophenylimino-4'-formylphenoxy)-1,3,5-triazine, Journal of Macromolecular Science Part a-Pure and Applied Chemistry, 45 (12), 1074-1079.
8. Koc, Z. E. and Uysal, A., (2016), Investigation of novel monopodal and dipodal oxy-Schiff base triazine from cyanuric chloride: Structural and antimicrobial studies, Journal of Macromolecular Science Part a-Pure and Applied Chemistry, 53 (2), 111-115.

9. Kopel, P., Sindelar, Z. and Klicka, R., (1998), Complexes of iron(III) salen and saloph Schiff bases with bridging dicarboxylic and tricarboxylic acids, Transition Metal Chemistry, 23 (2), 139-142.
10. Ozer, A., Yasa, D. E., Sahin, D. H., Turbayindir, H., Pehlivan, E. and Koc, Z. E., (2023), Investigation of microwave assisted synthesis of Schiff Base derived Metal-Chelates by liquid invert sugar containing D-Glucose, Inorganic and Nano-Metal Chemistry.
11. Tahmassebi, D. C. and Sasaki, T., (1998), Synthesis of a three-helix bundle protein by reductive amination, Journal of Organic Chemistry, 63 (3), 728-731.
12. Uysal, S., Koc, Z. E., Celikbilek, S. and Ucan, H. I., (2012), Synthesis of Star-Shaped Macromolecular Schiff Base Complexes Having Melamine Cores and Their Magnetic and Thermal Behaviors, Synthetic Communications, 42 (7), 1033-1044.
13. Uysal, S., (2013), Synthesis of melamine based polymer complexes and their thermal degradations and magnetic properties, Journal of Inclusion Phenomena and Macrocyclic Chemistry, 76 (1-2), 223-230.
14. Uysal, S. and Koc, Z. E., (2016), Synthesis and characterization of dopamine substitue tripodal trinuclear [(salen/salophen/salpropen)M] (M=Cr(III), Mn(III), Fe(III) ions) capped s-triazine complexes: Investigation of their thermal and magnetic properties, Journal of Molecular Structure, 1109, 119-126.
15. Wang, X. D. and Zhang, Q., (2004), Synthesis, characterization, and cure properties of phosphorus-containing epoxy resins for flame retardance, European Polymer Journal, 40 (2), 385-395.
16. Wimmer, T., Kreuzer, F. H., Staudinger, G. and Nussstein, P., (1992), Synthesis of Novel Insoluble Cyclodextrin Polymers, Minutes of the Sixth International Symposium on Cyclodextrins, 106-109.
17. Yu, Q., Schwidom, D., Exner, A. and Carlsen, P., (2008), Synthesis of Novel Homo-N-Nucleoside Analogs Composed of a Homo-1,4-Dioxane Sugar Analog and Substituted 1,3,5-Triazine Base Equivalents, Molecules, 13 (12), 3092-3106.