Tripodal Schiff Base Compounds Containing Triazole and Mn3+ and Fe3+ Complexes: Synthesis, Characterization, and Investigation of Their Spectral Properties

Year 2023, , 482 - 493, 01.03.2023

Mustafa Bal , Ayşegül Köse

https://doi.org/10.21597/jist.1181421

Abstract

In this study, it was aimed to synthesize and elucidate the structure of tripodal Schiff bases, which are used in the fields of materials science, chemistry, and pharmacology, and especially for the synthesis of chemical sensor materials due to their very good tendency to form complexes with metals. For the synthesis of new Schiff base tripodal compounds and their complexation with metals; Tripodal compound was synthesized as a result of the reaction of 2-hydroxy-4-(prop-2-yn-1-yloxy) benzaldehyde and N1, N1-bis(2-aminoethyl) ethane-1,2-diamine. The obtained compounds were complexed with Fe3+ and Mn3+ metals. The structures of synthesized tripodal ligands and metal complexes were tried to be elucidated using IR, UV-vis, Photoluminescence, 1H-NMR, 13C-NMR spectroscopic methods.

Keywords

Schiff Bases, Tripodal Compounds, Metal Complex.

References

• Ballester, P., Costa, A., Deyà, P. M., Vega, M., Morey, J., & Deslongchamps, G. (1999). Influence of remote intramolecular hydrogen bonds on the thermodynamics of molecular recognition of cis-1, 3, 5-cyclohexanetricarboxylic acid. Tetrahedron letters, 40(1), 171-174.
• Berrocal, M. J., Cruz, A., Badr, I. H., & Bachas, L. G. (2000). Tripodal ionophore with sulfate recognition properties for anion-selective electrodes. Analytical chemistry, 72(21), 5295-5299.
• Brewer, C., Brewer, G., Patil, G., Sun, Y., Viragh, C., & Butcher, R. J. (2005). Conformational control of spin state in iron (II) tripodal imidazole complexes. Inorganica chimica acta, 358(12), 3441-3448.
• Fan, A., Hong, H. K., Valiyaveettil, S., & Vittal, J. J. (2002). A urea-incorporated receptor for aromatic carboxylate anion recognition. Journal of Supramolecular Chemistry, 2(1-3), 247-254.
• Gelinsky, M., Vogler, R., & Vahrenkamp, H. (2002). Tripodal pseudopeptides with three histidine or cysteine donors: synthesis and zinc complexation. Inorganic chemistry, 41(9), 2560-2564.
• Grazina, R., Gano, L., Šebestík, J., & Santos, M. A. (2009). New tripodal hydroxypyridinone based chelating agents for Fe(III), Al(III) and Ga(III): Synthesis, physico-chemical properties and bioevaluation. Journal of Inorganic Biochemistry, 103(2), 262-273.
• He, L., Gou, S., Shi, Q., Qian, M., & Duan, C. (1999). The formation of a Schiff base intermediate: a nickel(II) complex of an asymmetric tripodal ligand. Journal of chemical crystallography, 29, 207-210.
• Ikuta, Y., Ooidemizu, M., Yamahata, Y., Yamada, M., Osa, S., Matsumoto, N., ... & Tuchagues, J. P. (2003). A New Family of Spin Crossover Complexes with a Tripod Ligand Containing Three Imidazoles: Synthesis, Characterization, and Magnetic Properties of [FeIIH3LMe](NO3) 2. 1.5 H2O,[FeIIILMe].3.5 H2O,[FeIIH3LMe][FeIILMe] NO3, and [FeIIH3LMe][FeIIILMe](NO3) 2 (H3LMe= Tris [2-(((2-methylimidazol-4-yl) methylidene) amino) ethyl] amine). Inorganic chemistry, 42(22), 7001-7017.
• Kaur, K., & Baral, M. (2014). Synthesis of imine-naphthol tripodal ligand and study of its coordination behaviour towards Fe(III), Al(III), and Cr(III) metal ions. Bioinorganic Chemistry and Applications, 2014.
• Leniec, G., Kaczmarek, S. M., Typek, J., Kołodziej, B., Grech, E., & Schilf, W. (2007). Magnetic and spectroscopic properties of gadolinium tripodal Schiff base complex. Solid state sciences, 9(3-4), 267-273. Li, M. Y., Kurmoo, M., Wang, Z. M., & Gao, S. (2011). Metal‐Organic Niccolite: Synthesis, Structures, Phase Transition, and Magnetic Properties of [CH3NH2(CH2)2NH2CH3][M2(HCOO)6](M= divalent Mn, Fe, Co, Ni, Cu and Zn). Chemistry–An Asian Journal, 6(11), 3084-3096.
• Nath, M., Saini, P. K., & Kumar, A. (2010). New di-and triorganotin (IV) complexes of tripodal Schiff base ligand containing three imidazole arms: Synthesis, structural characterization, anti-inflammatory activity and thermal studies. Journal of Organometallic Chemistry, 695(9), 1353-1362.
• Quinn, W. A., Saeed, M. A., Powell, D. R., & Hossain, M. A. (2010). An anthracene-based tripodal chemosensor for anion sensing. International journal of environmental research and public health, 7(5), 2057-2070.
• Reinoso‐García, M. M., Verboom, W., Reinhoudt, D. N., Brisach, F. D., Arnaud‐Neu, F., & Liger, K. (2005). Solvent Extraction of Actinides and Lanthanides by CMP (O)‐and N‐Acyl (thio) urea‐tetrafunctionalized Cavitands: Strong Synergistic Effect of Cobalt Bis (dicarbollide) Ions. Solvent extraction and ion exchange, 23(3), 425-437.
• Salehzadeh, S., Golbedaghi, R., Rakhtshah, J., & Adams, H. (2021). A new series of manganese (II) complexes of three fully condensed Schiff base ligands derived from some symmetrical and asymmetrical tripodal tetraamines and 2-pyridinecarboxyaldehyde. Journal of Molecular Structure, 1245, 130982.
• Schilf, W., Kamieński, B., Kołodziej, B., & Grech, E. (2004). The NMR study of hydrogen bond formation in some tris (((-salicylidene) amino) ethyl) amine derivatives in solution and in the solid state. Journal of molecular structure, 708(1-3), 33-38.
• Tasiopoulos, A. J., Wernsdorfer, W., Abboud, K. A., & Christou, G. (2004). A Reductive‐Aggregation Route to [Mn12O12(OMe)2(O2CPh)16(H2O)2]2− Single‐Molecule Magnets Related to the [Mn12] Family. Angewandte Chemie, 116(46), 6498-6502.
• Vigato, P. A., & Tamburini, S. (2004). The challenge of cyclic and acyclic Schiff bases and related derivatives. Coordination Chemistry Reviews, 248(17-20), 1717-2128.