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Oxovanadium(IV) complexes containing tetradentate N2O2-type ligands: synthesis, crystal structure, antioxidant activity, and spectroscopic characterization

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Abstract

Two coordination complexes were synthesized using vanadyl(IV) acetylacetonate and H2denm/H4dpim in MeOH/CHCl3 and characterized. The complexes were [VO(denm)(H2O)]·CH3OH (1) and [VO(H2dpim)(CH3COONa)]·CH3OH (2) (H2denm = 2,2′-[[(1R,2R)-1,2-diphenyl-1,2-ethanediyl]bis[(E)-nitrilomethylidyne]]bis[6-methoxyphenol]; H4dpim = [(2,2-dimethyl-1,3-propanediyl)bis(iminomethylene)bis(6-methoxyphenol)]. The vanadyl(IV) species of 1 and 2 exhibited distorted octahedral geometries with two N and two O atoms of each ligand and aqua/acetate ligand. Complex 1 did not exhibit emissions in the solid and solution states, whereas complex 2 exhibited strong band maxima in the solid state and a dimethyl sulfoxide solution. The magnetic properties and electron paramagnetic resonance spectra of 1 and 2 revealed that they were S = 1/2 spin systems. The antioxidant activity of 2 was higher than those of 1 and ascorbic acid.

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References

  1. Borisova, N.E., Kostin, A.A., Reshetova, M.D., Lyssenko, K.A., Belova, E.V., Myasoedov, B.F.: The structurally rigid tetradentate N,N’,o,O’-ligands based on phenanthroline for binding of f-elements: The substituents vs. structures of the complexes. Inorg. Chim. Acta. 478, 148 (2018)

    Article  CAS  Google Scholar 

  2. Noritake, Y., Umezawa, N., Kato, N., Higuchi, T.: Manganese salen complexes with acid – base catalytic auxiliary: Functional mimetics of catalase. Inorg. Chem. 52, 3653 (2013)

    Article  CAS  PubMed  Google Scholar 

  3. Duan, Y.-L., Hu, Z.-J., Yang, B.-Q., Ding, F.-F., Wang, W., Huang, Y., Yang, Y.: Zirconium and hafnium complexes bearing pyrrolidine derived salalen-type {ONNO} ligands and their application for ring-opening polymerization of lactides. Dalton Trans. 46, 11259 (2017)

    Article  CAS  PubMed  Google Scholar 

  4. Teixeira, F., Mosquera, R.A., Melo, A., Freire, C., Cordeiro, M., N.D.S: Principal component analysis of Mn(salen) catalysts. Phys. Chem. Chem. Phys. 16, 25364 (2014)

    Article  CAS  PubMed  Google Scholar 

  5. Pander, P., Franca, L.G., Dias, F.B., Kozhevnikov, V.N.: Electroluminescence of tetradentate pt(II) complexes: O^N^N^O versus C^N^N^O coordination. Inorg. Chem. 62, 5772 (2023)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Das, A., Bhattacharya, K., Giri, S., Ghosh, A.: Synthesis, crystal structure and magnetic properties of a dinuclear and a trinuclear ni(II) complexes derived from tetradentate ONNO donor Mannich base ligands. Polyhedron. 134, 295 (2017)

    Article  CAS  Google Scholar 

  7. Gogoi, H.P., Barman, P.: Salophen type ONNO donor Schiff base complexes: Synthesis, characterization, bioactivity, computational, and molecular docking investigation. Inorg. Chim. Acta. 556, 121668 (2023)

    Article  CAS  Google Scholar 

  8. Kurz, H., Schötz, K., Papadopoulos, I., Heinemann, F.W., Maid, H., Guldi, D.M., Köhler, A., Hörner, G., Weber, B.: A fluorescence-detected coordination-induced spin state switch. J. Am. Chem. Soc. 143, 3466 (2021)

    Article  CAS  PubMed  Google Scholar 

  9. Long, J.: Luminescent Schiff-base lanthanide single-molecule magnets: The association between optical and magnetic properties. Front. Chem. 7, 63 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Pander, P., Bulmer, R., Martinscroft, R., Thompson, S., Lewis, F.W., Penfold, T.J., Dias, F.B., Kozhevnikov, V.N.: 1,2,4-Triazines in the synthesis of bipyridine bisphenolate ONNO ligands and their highly luminescent tetradentate pt(II) complexes for solution-processable OLEDs. Inorg. Chem. 57, 3825 (2018)

    Article  CAS  PubMed  Google Scholar 

  11. Langeslay, R.R., Kaphan, D.M., Marshall, C.L., Stair, P.C., Sattelberger, A.P., Delferro, M.: Catalytic applications of vanadium: A mechanistic perspective. Chem. Rev. 119, 2128 (2019)

    Article  CAS  PubMed  Google Scholar 

  12. Choo, J., Jeong, A.R., Yeo, H., Hayami, S., Min, K.S.: Synthesis, crystal structure, and photoluminescent properties of mononuclear Er(III) and yb(III) complexes showing near-infrared emission. J. Mol. Struct. 1206, 127726 (2020)

    Article  CAS  Google Scholar 

  13. Arthur, J.L., Min, K.S., Miller, J.S.: Molecular tristability of CoII(salen)-based (salen = N,N’-ethylenebis(salicylideniminato) compounds. J. Mag Mag Mater. 489, 165375 (2019)

    Article  CAS  Google Scholar 

  14. Dragancea, D., Talmaci, N., Shova, S., Novitchi, G., Darvasiová, D., Rapta, P., Breza, M., Galanski, M.S., Kožı́šek, J., Martins, N.M.R., Martins, L.M.D.R.S., Pombeiro, A.J.L., Arion, V.B.: Vanadium(V) complexes with substituted 1,5-bis(2-hydroxybenzaldehyde)carbohydrazones and their use as catalyst precursors in oxidation of cyclohexane. Inorg. Chem. 55, 9187 (2016)

    Article  CAS  PubMed  Google Scholar 

  15. Sutradhar, M., Martins, L.M.D.R.S., da Silva, M.F.C.G., Pombeiro, A.J.L.: Vanadium complexes: Recent progress in oxidation catalysis. Coord. Chem. Rev. 301–302, 200 (2015)

    Article  Google Scholar 

  16. Jin, Y., Lee, H.-I., Pyo, M., Lah, M.S.: A linear trinuclear mixed valence vanadium(V/IV/V) complex: Synthesis, characterization, and solution behavior. Dalton Trans. 4, 797–803 (2005)

    Article  Google Scholar 

  17. Alajrawy, O.I., Tuleab, S.F., Alshammary, E.T.: Vanadium(IV) and vanadium(V) complexes: Syntheses, structural characterization, DFT studies and impact of oral uptake on enhancing insulin activity of diabetic albino rats. J. Mol. Struct. 1269, 133821 (2022)

    Article  CAS  Google Scholar 

  18. Dorn, M., Kalmbach, J., Boden, P., Päpcke, A., Gómez, S., Förster, C., Kuczelinis, F., Carrella, L.M., Büldt, L.A., Bings, N.H., Rentschler, E., Lochbrunner, S., González, L., Gerhards, M., Seitz, M., Heinze, K.: A vanadium(III) complex with blue and NIR-II spin-flip luminescence in solution. J. Am. Chem. Soc. 142, 7947 (2020)

    Article  CAS  PubMed  Google Scholar 

  19. Zhang, G., Scott, B.L., Wu, R., Silks, L.A., Hanson, S.K.: Aerobic oxidation reactions catalyzed by vanadium complexes of bis(phenolate) ligands. Inorg. Chem. 51, 7354 (2012)

    Article  CAS  PubMed  Google Scholar 

  20. Mathavan, A., Ramdass, A., Rajagopal, S.: Kinetic study of the oxovanadium(IV)-salen-catalyzed H2O2 oxidation of phenols. Transition Met. Chem. 40, 355 (2015)

    Article  CAS  Google Scholar 

  21. Banerjee, A., García, C.J.G., Benmansour, S., Gomlia, R.M., Frontera, A., Chattopadhyay, S.: Field-induced single-molecule magnet behaviour in a series of dinuclear cobalt(III,II) complexes. Polyhedron. 220, 115802 (2022)

    Article  CAS  Google Scholar 

  22. Huang, H., Sun, R., Wu, X.-F., Liu, Y., Zhan, J.Z., Wang, B.-W., Gao, S.: Circularly polarized luminescence and magneto-optic effects from chiral Dy(III) single molecule magnets. Dalton Trans. 52, 7646 (2023)

    Article  CAS  PubMed  Google Scholar 

  23. APEX3, v2019.1-0; Bruker: Madison, WI, USA: (2019)

  24. SADABS: version 2016/2, Bruker AXS Inc., Madison, WI, USA (2016)

  25. Sheldrick, G.M.: Phase annealing in SHELX-90: Direct methods for larger structures. Acta Crystallogr. A46, 467 (1990)

    Article  CAS  Google Scholar 

  26. Sheldrick, G.M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71, 3 (2015)

    Google Scholar 

  27. Apak, R., Güçlü, K., Özyürek, M., Karademir, S.E.: Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine: CUPRAC method. J. Agric. Food Chem. 52, 7970 (2004)

    Article  CAS  PubMed  Google Scholar 

  28. Hoshina, T.-A., Tsuchihashi, N., Ibuki, K., Ueno, M.: Electric conductivities of 1: 1 electrolytes in liquid methanol along the liquid–vapor coexistence curve up to the critical temperature. I. NaCl, KCl, and CsCl solutions. J. Chem. Phys. 120, 4355 (2004)

    Article  CAS  PubMed  Google Scholar 

  29. Nakamoto, K.: Infrared and Raman Spectra of Inorganic and Coordination Compounds part B, 6th edn., pp. 96–104. Wiley, New Jersey (2009)

    Google Scholar 

  30. Borah, R., Lahkar, S., Deori, N., Brahma, S.: Synthesis, characterization and application of oxovanadium(IV) complexes with [NNO] donor ligands: X-ray structures of their corresponding dioxovanadium(V) complexes. RSC Adv. 12, 13740 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  31. Mirdya, S., Basak, T., Chattopadhyay, S.: Photocatalytic ability of two hetero-tetranuclear complexes with CuO2Cd cores to degrade methylene blue: Influence of their structures on activity. Polyhedron. 170, 253 (2019)

    Article  CAS  Google Scholar 

  32. Kasumov, V.T., Köksal, F., Aslanoglu, M., Yerli, Y.: Synthesis, spectroscopic characterization and reactivity studies of oxovanadium(IV) complexes with bulky N,N′-polymethylenebis(3,5-tBu2salicylaldimine) ligands. Spectrochim. Acta A Mol. Biomol. Spectrosc. 77, 630 (2010)

    Article  PubMed  Google Scholar 

  33. Fang, X., Yang, X., Li, D., Lu, B., Yan, D.: Modification of π–π interaction and charge transfer in ratiometric cocrystals: Amplified spontaneous emission and near-infrared luminescence. Cryst. Growth Des. 18, 6470 (2018)

    Article  CAS  Google Scholar 

  34. Fourmigué, M., Batail, P.: Activation of hydrogen- and halogen-honding interactions in tetrathiafulvalene-based crystalline molecular conductors. Chem. Rev. 104, 5379 (2004)

    Article  PubMed  Google Scholar 

  35. Jeong, A.R., Shin, H.J., Jang, Y.J., Min, K.S.: Two-dimensional zinc (II) and copper (I) coordination polymers for photoluminescence. J. Mol. Struct. 1251, 132031 (2022)

    Article  CAS  Google Scholar 

  36. Jeon, S., Jeong, Y., Le, N.T.A., Ju, J., Cho, D., Jang, Y.J., Tokunaga, R., Hayami, S., Min, K.S.: Synthesis, crystal structure, luminescent properties, and magnetic properties of lanthanide(III) complexes containing the chiral (S,S/R,R)-N,N’-bis(3,5-dinitrosalicylidene)-1,2-cyclohexanediamine ligand. J. Ind. Eng. Chem. 128, 275 (2023)

  37. Rabouw, F.T., Prins, P.T., Villanueva-Delgado, P., Castelijns, M., Geitenbeek, R.G., Meijerink, A.: Quenching pathways in NaYF4: Er3+, Yb3+ upconversion nanocrystals. ACS Nano. 12, 4812 (2018)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  38. Grant, C.V., Geiser-Bush, K.M., Cornman, C.R., Britt, R.D.: Probing the molecular geometry of five-coordinate vanadyl complexes with pulsed ENDOR. Inorg. Chem. 38, 6285 (1999)

    Article  CAS  PubMed  Google Scholar 

  39. Stoll, S., Schweiger, A.: EasySpin, a comprehensive software package for spectral simulation and analysis in EPR. J. Magn. Reson. 178, 42 (2006)

    Article  CAS  PubMed  Google Scholar 

  40. Keskin, B., Yerli, Y., Avciata, U.: Synthesis and EPR studies of soluble vanadyl octakis(4-tert-butylbenzylthio)porphyrazine. J. Coord. Chem. 66, 2615 (2013)

    Article  CAS  Google Scholar 

  41. Kahn, O.: Molecular Magnetism. VCH (1993)

  42. Lagostina, V., Carniato, F., Esteban-Gómez, D., Platas-Iglesias, C., Chiesa, M., Botta, M.: Magnetic and relaxation properties of vanadium(IV) complexes: An integrated 1H relaxometric, EPR and computational study. Inorg. Chem. Front. 10, 1999 (2023)

    Article  CAS  Google Scholar 

  43. Machin, D.J., Murray, K.S.: The magnetic properties of some vanadium(IV) complexes. J. Chem. Soc. A. 1967, 1330–1332 (1967)

    Article  Google Scholar 

  44. Sarhan, A.M., Elsayed, S.A., Mashaly, M.M., El-Hendawy, A.M.: Oxovanadium(IV) and ruthenium (II) carbonyl complexes of ONS-donor ligands derived from dehydroacetic acid and dithiocarbazate: Synthesis, characterization, antioxidant activity, DNA binding and in vitro cytotoxicity. Appl. Organomet. Chem. 33, e4655 (2019)

    Article  Google Scholar 

  45. Ilhan-Ceylan, B., Tuzun, E., Kurt, Y., Acikgoz, M., Kahraman, S., Atun, G., Ulkuseven, B.: Oxovanadium(IV) complexes based on S-alkyl-thiosemicarbazidato ligands. Synthesis, characterization, electrochemical, and antioxidant studies. J. Sulfur Chem. 36, 434 (2015)

    Article  CAS  Google Scholar 

  46. Abdel-Rahman, L.H., Abu-Dief, A.M., Moustafa, H., Hamdan, S.K.: Ni(II) and Cu(II) complexes with ONNO asymmetric tetradentate Schiff base ligand: Synthesis, spectroscopic characterization, theoretical calculations, DNA interaction and antimicrobial studies. Appl. Organometal Chem. 31, e3555 (2017)

    Article  Google Scholar 

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Acknowledgements

This research was supported by Basic Science Research Program (no. 2021R1F1A1062108) through the National Research Foundation of Korea (NRF).

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Authors and Affiliations

  1. Department of Chemistry, Kyungpook National University, Daegu, 41566, Republic of Korea

    Ngoc Tram Anh Le

  2. Department of Chemistry Education and Science Education Research Institute, Kyungpook National University, Daegu, 41566, Republic of Korea

    Yuri Jeong & Kil Sik Min

  3. College of Basis Education, Yeungnam University, Gyeongsan, Gyeong-buk, 38541, Republic of Korea

    Yoon Jung Jang

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NTAL and KSM performed the experiments and analyzed the spectroscopic data, YJ and KSM performed the experiments and analyzed the magnetic data, YJJ and KSM analyzed the photoluminescent and catalytic data, NTAL and KSM wrote the paper.

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Correspondence to Kil Sik Min.

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Le, N.T.A., Jeong, Y., Jang, Y.J. et al. Oxovanadium(IV) complexes containing tetradentate N2O2-type ligands: synthesis, crystal structure, antioxidant activity, and spectroscopic characterization. J Incl Phenom Macrocycl Chem (2024). https://doi.org/10.1007/s10847-023-01215-z

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