Synthesis, characterization, industrial and biological studies of azo dye ligand and their some metallic ions

Authors

  • Abaas Obaid Hussein Medical Laboratory Technology Department, College of Medical Technology, the Islamic University, Najaf, Iraq.
  • Rana Abdulilah Abbas Chemical Industrial Department, Institute of Technology, Middle Technical University, Baghdad, Iraq.
  • Jinan M. M. Al-Zinkee Department of Chemistry, College of science, University of Diyala, Diyala, Iraq.
  • AmerJ. Jarad Department of Chemistry, College of Education for Pure Science Ibn-Al-Haitham, University of Baghdad, Baghdad, Iraq. https://orcid.org/0000-0001-7073-6011

DOI:

https://doi.org/10.21123/bsj.2024.8319

Keywords:

azo dyes, biological activity, 4-aminoantipyrine, metal complexes, textile industry.

Abstract

4-((2-hydroxy-3,5-dinitrophenyl)diazenyl)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one was produced through the reaction of diazonium salt from 4-amino antipyrine with 2,4-dinitrophenol. This ligand is examined by (UV-Vis, FTIR,1H,13CNMR, and LC-Mass) spectral techniques and micro elemental analysis (C.H.N.O). Co(II), Ni(II), Cu(II), and Zn(II) complexes were also performed and depicted. Metal chelates were distinguished by utilizing flame atomic absorption, infrared analysis, and elemental, visible, as well as ultraviolet spectroscopy, in addition to conductivity and magnetic quantification. Methods of mole ratio and continuous contrast have been studied to determine the nature of the compounds. Beer's law was followed throughout a condensation reach of about  1×10-4 - 3×10-4 M/L. A higher molar absorbance was observed for compound solutions. Analytical data displayed all metal chelates in a 1:2 metal-ligand ratio. In general, the physicochemical data, and the octahedral geometry of the compounds are described. Compounds are tested in biological and dye studies

References

Fleischmann C, Lievenbrück M, Ritter H. Polymers and dyes: Developments and applications. Polymers. 2015; 7: 717–746. https://doi.org/10.3390/polym7040717.

Zhang H, Chan-Park M B, Wang M. Functional polymers and polymer–dye composites for food sensing, Macromol. Rapid Commun. 2020; 41: 1–17.https://doi.org/10.1002/marc.202000279.

Myek B, Sunday N, Agbamu O F. Synthesis and characterization of an azo dye and its iron complex.Fudma. J Sci. 2021; 5(4): 347-352. doi: https://doi.org/10.33003/fjs-2021-0504-750.

Alabidi1 H M, Farhan A M, Salh N S, Aljanaby A A J. New azo-Schiff compounds and metal complexes derived from 2-naphthol synthesis, characterization, spectrophotometric, and study of biological activity. Current Appl Sci Techn. 2023; 23(4): 1-14. https://doi.org/10.55003/cast.2022.04.23.007.

Moamen S R, Altalhi T, Safyah B B, Ghaferah H A, Kehkashan A. New Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Zn(II), Cd(II),and Hg(II) Gibberellate Complexes: Synthesis, structure, and inhibitory activity against COVID-19 protease. Russ J Gen Chem. 2021; 91(5): 890–896. https://doi.org/10.1134/S1070363221050194.

Maurice K, Mariam AC, Katia NN, Awawou GP, Sally-Judith EN, Peter TN. Synthesis, characterization and antimicrobial studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes of (E)-2-(4-dimethylbenzydimino)-glycylglycine,(Glygly-DAB) a Schiff base derived from 4-dimethylaminobenzaldehyde and glycylglycine. Int J Org Chem. 2018; 8: 298-308. https://doi.org/10.4236/ijoc.2022.124015.

Hamza IS, Mahmmoud WA, Al-Hamdani AAS, Ahmed SD, Allaf AW, AlZoubi W. Synthesis, characterization, and bioactivity of several metal complexes of (4-Amino-N-(5-methyl-isaxazol-3-yl)-benzenesulfonamide). Inorg Chem Commun. 2022; 24(144): 109776. https://doi.org/10.1016/j.inoche.2022.109776.

Dahi MA, Jarad A J. Synthesis, characterization and biological evaluation of thiazolyl azo ligand complexes with some metal ions. J Phys Conf. 2020; 1664(012090): 1-18. https://doi.org/10.1088/1742-6596/1664/1/012090.

Jana B, Bhattacharyya S, Patra A. Perspective of dye-encapsulated conjugated polymer nanoparticles for potential applications, Bull Mater Sci. 2018; 41: 122. https://doi.org/10.1007/s12034-018-1643-x.

Oyarce E, Butter B, Santander P, Sánchez J. Polyelectrolytes applied to remove methylene blue and methyl orange dyes from water via polymer-enhanced ultrafiltration. J Environ Chem Eng. 2021; 9(6): 106297. https://doi.org/10.1016/j.jece.2021.106297.

Nair MLH, Mathew G, Kumar MRS. Synthesis and characterization of some new Cu(II) complexes of azo dyes derived from 1,2-dihydro-1,5-dimethyl-2-phenyl-4-amino-3H-pyrazol-3-one. Indian J Chem. 2005; 44: 85-89.

Li J, Fan J, Cao R, Zhang Z, Du J, Peng X. Encapsulated dye/polymer nanoparticles prepared via miniemulsion polymerization for inkjet printing. ACS Omega. 2018; 3: 7380–7387. https://doi.org/10.1021/acsomega.8b01151.

Hussein AO, Abbas RA, Sultan JS, Jarad AJ. Synthesis and characterization of metal(II) complexes with azo dye ligand and their industrial and biological applications. Egypt J Chem. 2021; 64(11): 6717-6724. https://doi.org/10.21608/EJCHEM.2021.68770.3530.

Kirill VY, Aleksandr SS, Werner K, Sergey AG. Synthesis, crystal chemistry of octahedral Rhodium(III) Chloroamines. Molecules. 2020; 25(768): 1-17. https://doi.org/10.3390/molecules25040768.

Al-Khazraji AMA, Al Hassani RAM. Synthesis, characterization and spectroscopic study of new metal complexes form heterocyclic compounds for photostability study. Syst Rev Pharm. 2020; 11(5): 535-555.

Al-Sheikh M, Medrasi HY, Sadek KU, Mekheimer RA. Synthesis and spectroscopic properties of new azo dyes derived from 3-ethylthio-5-cyanomethyl-4-phenyl-1,2,4-triazole. Molecules. 2014; 19(3): 2993-3003. https://doi.org/10.3390/molecules19032993.

Shaalan N D, Abdulwahhab S. Synthesis, characterization and biological activity study of some new metal complexes with Schiff's bases derived from [o-vanillin] with [2-amino-5-(2-hydroxy-phenyl)-1,3,4-thiadiazole]. Egypt J Chem. 2021; 64(8): 4059-4067. https://doi.org/10.21608/EJCHEM.2021.66235.3432.

Kirill VY, Aleksandr SS, Werner K, Sergey AG. Synthesis, Crystal Chemistry of Octahedral Rhodium(III) Chloroamines. Molecules. 2020; 25(768): 1-17. https://doi.org/10.3390/molecules25040768.

KofiKyei S, Onyewuchi A, Godfred D. Synthesis, characterization and antimicrobial activity of peanut skin extract-azo-compounds. Sci Afr. 2020; 8 (e00406): 1-14.https://doi.org/10.1016/j.sciaf.2020.e00406.

Al-Daffy RKH, Al-Hamdani AAS. Synthesis, characterization, and thermal analysis of a new acidic azo ligand's metal complexes. Baghdad Sci J. 2022; 3(19): 121-133. https://doi.org/10.21123/bsj.2022.6709.

GearyWJ. The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coord Chem Rev. 1971; 7: 81-122. http://dx.doi.org/10.1016/S0010-8545(00)80009-0.

Saadi L, Ghali AA. Synthesis and characterization of some metal complexes derived from azo ligand of 4,4' methylenedianiline and resorcinol. Biomed Chem Sci. 2022; 1(4): 241-248. https://doi.org/10.48112/bcs.v1i4.252.

Raghavendra KR, Kumar KA. Synthesis of some novel azo dyes and their dyeing, redox and antifungal properties, Int J Chem Tech Res. 2013; 5(4): 1756-1760.

Ravanasiddappa M, Sureshg T, Syed K, Radhavendray SC, Basavaraja C, Angadi SD. Transition metal complexes of 1,4(2-hydroxyphenyl-1-yl)di-iminoazine:synthesis, characterization and antimicrobial studies, E-J Chem. 2008; 5(2): 395-403. https://doi.org/10.1155/2008/328961.

Al-Khateeb Z T, Karam F F, Al-Adilee K. Synthesis and characterization of some metals complexes with new heterocyclic azo dye ligand 2-[2-(5- Nitro thiazolyl) azo]-4- methyl -5- nitro phenol and their biological activities. J Phys Conf. 2019; 1294 (052043): 1-18. https://doi.org/10.1088/1742-6596/1294/5/052043.

Kilinc D, Şahin O, Horoz S. Use of low cost Zn(II) complex efciently in a dye sensitized solar cell device. J Mater Sci Mater Electron. 2019; 30: 11464–11467. https://doi.org/10.1007/s10854-019-01497-5.

Oloyede H O, Woods J A O, Gorls H, Plass W, Eseola A O. N-donor-stabilized Pd(II) species supported by sulphonamide-azo ligands: Ligand architecture, solvent co-ligands, CeC coupling. J Mol Struct. 2020; 1199(127030): 1-11. https://doi.org/10.1016/j.molstruc.2019.127030.

Anacona J, Pineda Y, Bravo A, Camus J. Synthesis, characterization and antibacterial activity of a tridentate Schiff base derived from Cephalexin and 1,6-hexanediamine and its transition metal complexes. Med Chem. 2016; 6(7): 467-473. https://dx.doi.org/10.4172/2161-0444.1000385.

Sahap EH, Sajad FAA, Al-Labban HMY. Incorporation of nickel with azo dye and its applications in dye-sensitized solar cells. Int J Drug Del Tech. 2022; 12(2): 603-609.

Lateef SM , Ismail AA . Synthesis a novel complexes of VO(II),Mn(II),Fe(II) ,Co(II), Ni(II), Cu(II)and Pt(IV) derived from Schiff’s base of pyridoxal and 2-amino-4-nitrophenol and study their biological activates. Ibn Al-Haith J Pur Appl Sci. 2023; 36(2): 259-275. https://doi.org/10.30526/36.2.3054.

Abdulammer JH, Alis MF. Heavy metal complexes of 1,2,3-triazole derivatives: synthesis, characterization, and cytotoxicity appraisal against breast cancer cell lines (MDA- MB-231). Baghdad Sci J. 2022; 19(6): 1410-1422.https://doi.org/10.21123/bsj.2022.7178.

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2024-10-01

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Synthesis, characterization, industrial and biological studies of azo dye ligand and their some metallic ions. Baghdad Sci.J [Internet]. 2024 Oct. 1 [cited 2024 Oct. 13];21(10):3108. Available from: https://bsj.uobaghdad.edu.iq/index.php/BSJ/article/view/8319

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