the Synthesis and characterization of (E)-5-((2-hydroxynaohthalen-1-yl) diazenyl))-2,3-dihydrophthalazine-1,4-dione complexes with Some Metal ions and their industrial and biological applications

luminol derivatives

Authors

DOI:

https://doi.org/10.24237/04.01.425

Keywords:

Azo dye complexes,, Azo dye,, Bioactivity, Industrial applications, , Mass spectra.

Abstract

When 2-naphthol is reacted with the diazonium salt of 5-amino-2,3-dihydrophthalazine-1,4-dione, (E)-5-((2-hydroxynaphthalen-yl)diazenyl))-2,3-dihydrophthalazine-1,4-dione is produced. Utilized microelemental analysis (C.H.N.O.) and spectroscopic studies (FTIR, UV-Vis, 1H and 13C-NMR, Mass) to determine the azo ligand. . Metal chelates of transition metals were prepared and analyzed using mass spectra, atomic absorption of flame, elemental analysis, infrared and UV-Vis spectral processes, as well as conductivity and magnetic measurements. The nature of the compounds produced has been studied following the mole ratio and continuous contrast methods, and Beer's law was followed during a concentration scope (1×10-4 - 3×10-4 mol/L). High molar absorptivity of compound solutions has been noticed. Analytical data showed that all the complexes are outo 1:2 metal-ligand ratio, except for the palladium complex, which has appeared at a 1:1 ratio. At the radix for physicochemical datum, an octahedral structure has been described for Ni(II) and Pt(IV) complexes and a square planar structure for the Pd(II) complex.  Biological activity has been explored in connection to the effects of these complexes on blood lymphocyte division in the presence of PHA. The findings show that at different concentrations, Lpd causes a halt in cell division, which is more apparent. Furthermore, by generating a sustained mitotic block during the metaphase/anaphase, ligand (L) inhibited the proliferation of lymphocyte cell lines. Apart from that, using the chemicals produced to dye cotton fabric was a workable method. Dye stability under light and detergent conditions has been investigated.

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Author Biographies

  • Dr. Jinan M. M. Al-Zinkee, University of Diyala

    Dr. Jinan M. M. Al-Zinkee is an associate professor in the inorganic chemistry department of Chemistry, College of science, University of Diyala, Diyala, Iraq. she can be contacted at email:

  • Eman khalil lbrahem  , Ministry of Education

    Eman khalil lbrahem  is the teacher at  ministry of Education she received the B.Sc degree  in chemistry science from University of Diyala in lraq and M.Sc  degree in chemistry science from University of Diyala . she can be contacted at email: emankhilil327@gmail.com.

  • Dr. Amer J. Jarad, Ibn-Al-Haitham, University

    Dr. Amer J. Jarad is  Professor at Inorganic Chemistry Department of Chemistry, College of Education for Pure science /Ibn-Al-Haitham, University of Baghdad, Baghdad, Iraq. he can be contacted at email: :    Amir.j.j@ihcoedu.uobaghdad.edu.iq

References

[1] Ali, R.R. and Mohammed, H.S. 2021. Synthesis and characterization and biological study of pyridylazo ligand and its compounds of Co, Ni and Cu divalent ions, Journal of Physics: Conference Series, 1999, 012009. DOI: 10.1088/1742-6596/1999/1/012009

[2] Mohammed,H.S.,Tripathi, V.D. and Darghouth, A.A. 2019 Synthesis, Characterization, DFT calculation and Antimicrobial Activity of Co (II) and Cu(II) complexes with azo dye, Journal of Physics: Conference Series, 1294, 052051. DOI: 10.1088/1742-6596/1294/5/052051

[3] Bouhdada, M., Amane, M.E. and El Hamzaoui, N. 2019. Synthesis, spectroscopic studies, X-ray powder diffraction data and antibacterial activity of mixed transition metal complexes with sulfonate azo dye, sulfamate and caffeine ligands, Inorganic Chemistry Communications, 10,1 32–39. https://doi.org/10.1016/j.inoche.2019.01.005

[4] Sayhood, A.A. and Mohammed, H. 2015. Synthesis of new azo reagent for determination of Pd(II),Ag(I) and applied to enhance the properties of silver nano particles, Int. J. Chem. Sci., 13(3),1123-1136.

[5] Ali1, F.J., AL-Ameri, L.A.M. and Ali, A.M. 2021. Synthesis and identification and biological studies of new azo dyes derived from imidazole and their chelate complexes, Indian Journal of Forensic Medicine and Toxicology, 15( 2),1253-1260. https://doi.org/10.37506/ijfmt.v15i2.14496

[6] Mahmoud, W.H., Sayed, F.N. and Mohamed, G.G. 2016. Synthesis, characterization and in vitro antimicrobial and anti-breast cancer activity studies of metal complexes of novel pentadentate azo dye ligand, Applied Organometallic Chemistry, 30(11), 959–973.

[7] Manna, C.K., Naskar, R. and Mondal, T.K. 2019. Palladium (II) complex with 1-(2-pyridylazo)-2-naphthol (PAN): synthesis, X-ray structure, electrochemistry, DFT computation and DNA binding study,” Journal of the Indian Chemical Society, 96(5),599–606. https://doi.org/10.1016/J.POLY.2018.04.044

[8] Abd El-Wahaab, B., Elgendy, K. and El-didamony, A.2020. Synthesis and characterization of new azo-dye reagent and using to spectrophotometric determination of samarium(III) in some industrial and blood samples, Chemical Papers, 74(5),1439–1448. https://doi.org/10.1007/s11696-019-01000-8

[9] Abate,P.O., Sottile,M., Le´on,I.E., Vergara,M.M. and Katz,N.E. 2020. symmetrical dirhenium(I) complex with 4,4’’- Azobis(2,2’-bipyridine) as a bridging ligand: synthesis, physicochemical properties and applications in detection of biologically relevant thiols and in chemotherapy for bone cancer, Journal of the Brazilian Chemical Society, 31(11), 2299–2306. https://doi.org/10.21577/0103-5053.20200085

[10] AL-Adilee,K.J., Abass ,A.K. and Taher,A.M. 2016. Synthesis of some transition metal complexes with new heterocyclic thiazolyl azo dye and their uses as sensitizers in photo reactions, Journal of Molecular Structure, 1108, 378e397. http://dx.doi.org/10.1016/j.molstruc.2015.11.038

[11] Al-Zinkeei,J.M.M. and Jard.A.J. 2019. Synthesis, characterization and microbial evaluation of heterocyclic azo dye ligand complexes of some transition metal(II) Ions, Asian Journal of Chemistry,31(3),727-732. https://doi.org/10.14233/ajchem.2019.21800

[12] Verma, R. S., & Babu, A. (1989). Human chromosomes: manual of basic techniques.

[13] Carballo,R., Castineras,A., Covelo,B., Niclos,J. and Vazjuez-Lopez,E.M. 2001. Synthesis and characterization of a potassium complex of magneson: [K(HL)(OH2)2]∞ [H2L=4-(4-nitrophenylazo)resorcinol (magneson)], Polyhedron, 20,2415-2420. DOI: 10.1016/S0277-5387(01)00842-7

[14] Fayadh,R.H., Ali,A.A. and Al-Jabri,F.M. 2015. Synthesis and identification symmetrically azo dyes derived from sulfa compounds and spectrophotometric study of Nickel (II) complexes with prepared dyes, International Journal of Engineering and Technical Research, 3(3),24-28.

[15] Adbulrazzaq,A.G. and Al-Hamdani, A.A.S. 2023. Some metal ions complexes with azo [4-((8-hydroxyquinolin-7-yl)-N(4-methylisoxazol-3-yl)benzenesulfonamide] :Synthesis, characterization, thermal study and antioxidant activity. Journal of Medicinal and Chemical Sciences, 6(2),236-249. DOI: 10.26655/JMCHEMSCI.2023.2.7

[16] Nguyen,A.V., Vu,A.T.N., Bazan,L.V., Galeev, R.T., Utenyshev,A.N., Markova, E.B., Le, V.T. and Kovalchukova, O.V. 2022. Synthesis, characterization and sorption activity of novel azo-colorants derived from phloroglucinol and antipyrine and their metal complexes. Royal Society of Chemistry, 12,888-898. https://doi.org/10.1039/D1RA07254D

[17] Cao,H.W and Zhao,J.F. 2003. Stability constants of cobalt(II) and copper(II) with 3-[(o-carboxy-p-nitrobenzene)azo] chromotropic acid and selective determination of copper(II) by competition coordination, Croatica Chemica Acta.,76,1-6.

[18] G.Wtter, N.Ludwig and S.Horst; "Thermodynamics and statistical mechanics", Springer-Verlag, (1996)101.

[19] Geary, W.J. (1971) The Use of Conductivity Measurements in Organic Solvents for the Characterisation of Coordination Compounds. Coordination Chemistry Reviews, 7, 81-122. http://dx.doi.org/10.1016/S0010-8545(00)80009-0

[20] Ibraham, EK, Al-Zinkee, JMM, Jarad, AJ. Feasible and simple preparation of Pd (II), Ni (II), and Pt (IV) complexes: Their biological and industrial applications and investigation of Pd (II) complex in Suzuki reaction. Iranian Journal of Catalysis.2024; 14(2): 142419 (1-17). https://doi.org/10.57647/j.ijc.2024.1402.19

[21] Patel,K.D. and Patel,H.S. 2017. Synthesis, spectroscopic characterization and thermal studies of some divalent transition metal complexes of 8-hydroxyquinoline, Arabian Journal of Chemistry, 10, S1328–S1335. https://doi.org/10.1016/j.arabjc.2013.03.019

[22] Al- Hasani, T.J. and Almaliky,Z.S. 2015. New Pd and Pt complexes of guanine –azo dye: structural, spectroscopic, dyeing performance and antibacterial activity studies, Iraqi Journal of Science, 56(4A), 2718-2731.

[23] Hussein,A.O., Abbas,R.A., Sultan,J.S. and Jarad,A.J. 2020. Synthesis and characterization of metal(II) complexes with azo dye ligand and their industrial and biological applications. Egyptian Journal of Chemistry, 64(11),6717-6724. DOI: 10.21608/EJCHEM.2021.68770.3530

[24] Jarad,A.J.,Kadhim,Z.S., Mahmood,M.A. and Obaid,S.M.H. 2016. Synthesis, spectral studies and biological activity of azo dye complexes with some metal ions. Journal of Global Pharma Technology, 10(06)97-106.

[25] Jarad,A.J. and Quiasim,S.H. 2018. Synthesis and characterization of azo dyes ligands complexes with Ni(II) and Cu(II) and studies their industrial and bacterial application. Research Journal Pharmaceutical ,Biological and Chemical Science, 9(2),631-642.

[26] Jarad,A.J., Majeed,I.Y. and Hussein, A.O. 2018. Synthesis and spectral studies of hetrocyclic azo dye complexes with some metals. Journal of Physics.Conference Series, 1003,0120021. DOI: 10.1088/1742-6596/1003/1/012021

[27] Al-Wabli,R.I., Resmi,K., Mary,Y.S., Panicker,C.Y., Attia,M.I., El-Eman, A.A. and Alsenoy,C.V. 2016. Vibrational spectroscopic studies, fukui functions, HOMO-LUMO, NLONBO analysis and molecular docking study of (E)-1-(1,3-benzodioxol-5-yl)4,4-dimethylpent-1-en-3-one, a potential precursor to bioactive agents, Journal of Molecular Structure, 1123,375-383. DOI: 10.1016/j.molstruc.2016.07.044

[28] Hrichi,H., El-Kanzi,N.A., Ali,A.M. and Abou, A. 2023. A novel colorimetric chemosensor based on 2-[((carbamothioylhydrazazono)methyl]phenyl-4-methylbenzenesulfonate (CHMPMPS) for the detection of Cu(II) in aqueous medium, Res.Chem.Intermed., 49,2257-2276. DOI: 10.1007/s11164-022-04905-4

[29] Mohammed, I. H., Jaafar, G. H., Qaddoori, M. H., Abdulateef, M. H., & Abud, Z. T. (2021). effect of extraction on rhamnus carolnana plant in mice chromosome lymphocytes and microtubules hepg2 cancre cell line Biochemical & Cellular Archives, 21(1).

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Published

2026-01-30

How to Cite

mohammed, J., lbrahem, E., & Jarad, A. . (2026). the Synthesis and characterization of (E)-5-((2-hydroxynaohthalen-1-yl) diazenyl))-2,3-dihydrophthalazine-1,4-dione complexes with Some Metal ions and their industrial and biological applications: luminol derivatives. ٍِASJ - Academic Science Journal, 4(1), 43-58. https://doi.org/10.24237/04.01.425

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