{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T02:39:43Z","timestamp":1790649583493,"version":"4.1.0"},"reference-count":49,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2018,4,2]],"date-time":"2018-04-02T00:00:00Z","timestamp":1522627200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>We are reporting a novel azo-azomethine ligand, HL and its complexes with Cu(II) and Fe(III) ions. The ligand and its complexes are characterized by various physico-chemical techniques using C,H,N analyses, FT-IR, 1H-NMR, ESI-MS and UV-Vis studies. TGA analyses reveal complexes are sufficiently stable and undergo two-step degradation processes. The redox behavior of the complexes was evaluated by cyclic voltammetry. Furthermore, the ligand and its complexes were tested for antimicrobial activity against bacterial and fungal strains by determining inhibition zone, minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC). The complexes showed moderate antimicrobial activity when tested against Gram +ve and Gram \u2212ve bacterial strains. To obtain insights into the structure of ligand, DFT studies are recorded. The results obtained are quite close to the experimental results. In addition, the energy gap, chemical hardness, softness, electronegativity, electrophilic index and chemical potential were calculated using HOMO, LUMO energy value of ligand.<\/jats:p>","DOI":"10.3390\/molecules23040813","type":"journal-article","created":{"date-parts":[[2018,4,2]],"date-time":"2018-04-02T12:32:20Z","timestamp":1522672340000},"page":"813","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":46,"title":["Synthesis, Structural Characterization and Antimicrobial Activity of Cu(II) and Fe(III) Complexes Incorporating Azo-Azomethine Ligand"],"prefix":"10.3390","volume":"23","author":[{"given":"Mohammad","family":"Azam","sequence":"first","affiliation":[{"name":"Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Saud","family":"Al-Resayes","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Saikh","family":"Wabaidur","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mohammad","family":"Altaf","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bhaskar","family":"Chaurasia","sequence":"additional","affiliation":[{"name":"Coordination Chemistry Research Laboratory, Department of Chemistry, Govt. Science College, Jabalpur 482001, India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5188-1130","authenticated-orcid":false,"given":"Mahboob","family":"Alam","sequence":"additional","affiliation":[{"name":"Division of Chemistry and Biotechnology, Dongguk University, 123 Dongdae-ro, Gyeongju 780-714, Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Satyendra","family":"Shukla","sequence":"additional","affiliation":[{"name":"Coordination Chemistry Research Laboratory, Department of Chemistry, Govt. Science College, Jabalpur 482001, India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pratiksha","family":"Gaur","sequence":"additional","affiliation":[{"name":"Coordination Chemistry Research Laboratory, Department of Chemistry, Govt. Science College, Jabalpur 482001, India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nader","family":"Albaqami","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mohammad","family":"Islam","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Soonheum","family":"Park","sequence":"additional","affiliation":[{"name":"Department of Advanced Materials Chemistry, Dongguk University, 123 Dongdae-ro, Gyeongju 780-714, Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2018,4,2]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Hunger, K. (2003). Industrial Dyes. Chemistry, Properties, Applications, Wiley-VCH.","DOI":"10.1002\/3527602011"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"520","DOI":"10.1016\/j.molstruc.2017.08.016","article-title":"Multi-properties of a new azo-Schiff base and its binuclear copper(II) chelate: Preparation, spectral characterization, electrochemical, potentiometric and modeling studies","volume":"1149","author":"Sarigul","year":"2017","journal-title":"J. Mol. Struct."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"268","DOI":"10.1016\/j.ica.2015.03.010","article-title":"An azo-azomethine ligand and its copper (II) complex: Synthesis, X-ray crystal structure, spectral, thermal, electrochemical and photoluminescence properties","volume":"430","author":"Eren","year":"2015","journal-title":"Inorg. Chim. Acta"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"138","DOI":"10.1016\/j.molliq.2016.02.021","article-title":"Geometrical structure, potentiometric, molecular docking and thermodynamic studies of azo dye ligand and its metal complexes","volume":"218","author":"Mohamed","year":"2016","journal-title":"J. Mol. Liq."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"92","DOI":"10.1016\/j.molstruc.2015.06.048","article-title":"Electronic structure of thioether containing NSNO donor azo-ligand and its copper(II) complex: Experimental and theoretical studies","volume":"1099","author":"Pramanik","year":"2015","journal-title":"J. Mol. Struct."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"40","DOI":"10.1016\/j.dyepig.2005.10.005","article-title":"Synthesis and spectroscopic properties of new azo-dyes and azo-metal complexes derived from barbituric acid and aminoquinoline","volume":"73","author":"Gup","year":"2007","journal-title":"Dyes Pigments"},{"key":"ref_7","unstructured":"Peters, A.T., and Freeman, H.S. (1991). Colour Chemistry, the Design and Synthesis of Organic Dyes and Pigments, Elsevier Applied Science."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Gregory, P. (1991). High-Technology Applications of Organic Colorants, Plenum Press.","DOI":"10.1007\/978-1-4615-3822-6"},{"key":"ref_9","unstructured":"Grayson, M. (1985). Concise Encyclopedia of Chemical Technology, John Wiley & Sons."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1016\/j.saa.2014.01.005","article-title":"Spectroscopy and solvatochromism studies along with antioxidant and antibacterial activities investigation of azo\u2013azomethine compounds 2-(2-hydroxyphenylimino)methyl)-4-phenyldiazenyl)phenol","volume":"124","author":"Ghasemian","year":"2014","journal-title":"Spectrochim. Acta Part A Mol. Biomol. Spectrosc."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"691","DOI":"10.1007\/s00726-013-1539-4","article-title":"Asymmetric synthesis of \u03b1-amino acids via homologation of Ni(II) complexes of glycine Schiff bases; Part 1: Alkyl halide alkylations","volume":"45","author":"Sorochinsky","year":"2013","journal-title":"Amino Acids"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1017","DOI":"10.1007\/s00726-013-1580-3","article-title":"Asymmetric synthesis of \u03b1-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 2: Aldol, Mannich addition reactions, deracemization and (S) to (R) interconversion of \u03b1-amino acids","volume":"45","author":"Sorochinsky","year":"2013","journal-title":"Amino Acids"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"2047","DOI":"10.1007\/s00726-014-1764-5","article-title":"Asymmetric synthesis of alpha-amino acids via homologation of Ni(II) complexes of glycine schiff bases. Part 3: Michael addition reactions and miscellaneous transformations","volume":"46","author":"Acena","year":"2014","journal-title":"Amino Acids"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"21","DOI":"10.1016\/j.jfluchem.2013.06.004","article-title":"ChemInform Abstract: Synthesis of Fluorine-Containing \u03b1-Amino Acids in Enantiomerically Pure Form via Homologation of Ni(II) Complexes of Glycine and Alanine Schiff Bases","volume":"155","author":"Acena","year":"2013","journal-title":"J. Fluor. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1016\/j.arabjc.2011.11.004","article-title":"Synthesis, spectroscopic characterization and in vitro antimicrobial studies of Schiff base ligand, H2L derived from glyoxalic acid and 1,8-diaminonaphthalene and its Co(II), Ni(II), Cu(II) and Zn(II) complexes","volume":"9","author":"Shakir","year":"2016","journal-title":"Arab. J. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"309","DOI":"10.1016\/j.bjp.2014.07.008","article-title":"Study of the antimicrobial activity of metal complexes and their ligands through bioassays applied to plant extracts","volume":"24","author":"Santosa","year":"2014","journal-title":"Rev. Bras. Farmacogn."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"87","DOI":"10.1111\/febs.14315","article-title":"Mechanisms of proton relay and product release by Class A \u03b2-lactamase at ultrahigh resolution","volume":"285","author":"Lewandowski","year":"2018","journal-title":"FEBS J."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1673","DOI":"10.1021\/acs.organomet.6b00888","article-title":"Antibacterial Properties of Metallocenyl-7-ADCA Derivatives and Structure in Complex with CTX-M \u03b2-Lactamase","volume":"36","author":"Lewandowski","year":"2017","journal-title":"Organometallics"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1442","DOI":"10.1021\/cb4000844","article-title":"Analysis of the Mechanism of Action of Potent Antibacterial Hetero-tri-organometallic Compounds: A Structurally New Class of Antibiotics","volume":"8","author":"Wenzel","year":"2013","journal-title":"ACS Chem. Biol."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"6350","DOI":"10.1039\/c2dt12460b","article-title":"Small organometallic compounds as antibacterial agents","volume":"41","author":"Patra","year":"2012","journal-title":"Dalton Trans."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"4453","DOI":"10.1039\/C4SC01822B","article-title":"Highly active antibacterial ferrocenoylated or ruthenocenoylated Arg-Trp peptides can be discovered by an l-to-d substitution scan","volume":"5","author":"Albada","year":"2014","journal-title":"Chem. Sci."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Jab\u0142onski, A., Matczak, K., Koceva-Chy\u0142a, A., Durka, K., Steverding, D., Jakubiec-Krzesniak, K., Solecka, J., Trzybinski, D., Wozniak, K., and Andreu, V. (2017). Cymantrenyl-Nucleobases: Synthesis, Anticancer, Antitrypanosomal and Antimicrobial Activity Studies. Molecules, 22.","DOI":"10.3390\/molecules22122220"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/j.dyepig.2008.07.019","article-title":"New azo ligands containing azomethine groups in the pyridazine-based chain: Synthesis and characterization","volume":"81","author":"Khanmohammadi","year":"2009","journal-title":"Dyes Pigments"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"180","DOI":"10.1016\/j.saa.2013.09.070","article-title":"Synthesis and characterization of Cu(II), Co(II) and Ni(II) complexes of a number of sulfadrug azodyes and their application for wastewater treatment","volume":"121","author":"Sakai","year":"2014","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"449","DOI":"10.1016\/j.jphotobiol.2011.05.003","article-title":"Synthesis, spectroscopic and electrochemical studies of N,N-bis[(E)-2-thienylmethylidene]-1,8-naphthalenediamine and its Cu(II) complex: DNA cleavage and generation of superoxide anion","volume":"104","author":"Shakir","year":"2011","journal-title":"J. Photochem. Photobiol. B"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/j.molstruc.2014.01.001","article-title":"Design and structural studies of diimine\/CdX2 (X = Cl, I) complexes based on 2,2-dimethyl-1,3-diaminopropane ligand","volume":"1062","author":"Warad","year":"2014","journal-title":"J. Mol. Struct."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"568","DOI":"10.1039\/C4DT02112F","article-title":"Novel uranyl(vi) complexes incorporating propylene-bridged salen-type N2O2-ligands: A structural and computational approach","volume":"44","author":"Azam","year":"2015","journal-title":"Dalton Trans."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1069","DOI":"10.1016\/j.saa.2010.08.075","article-title":"A new salen base 5-(phenylazo)-N-(2-amino pyridine) salicyliden Schiff base ligand: Synthesis, experimental and density functional studies on its crystal structure, FTIR, 1H-NMR and 13C NMR spectra","volume":"77","author":"Sheikhshoaie","year":"2010","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"535","DOI":"10.1016\/S0009-2614(00)01135-0","article-title":"Investigation of third-order nonlinearity of an azo dye and its metal-substituted compounds","volume":"330","author":"Wu","year":"2000","journal-title":"Chem. Phys. Lett."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"3039","DOI":"10.1016\/S0277-5387(01)00901-9","article-title":"Synthesis of copper(II) and nickel(II) complexes using compartmental ligands: X-ray, electrochemical and magnetic studies","volume":"20","author":"Manonmani","year":"2001","journal-title":"Polyhedron"},{"key":"ref_31","unstructured":"Cotton, F.A., and Wilkinson, G. (1988). Advanced Inorganic Chemistry, Wiley. [5th ed.]."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"467","DOI":"10.1007\/s11243-008-9066-y","article-title":"Template synthesis and physicochemical studies of 14-membered hexaazmacrocyclic complexes with Co(II), Ni(II), Cu(II) and Zn(II): A comparative spectroscopic approach on DNA binding with Cu(II) and Ni(II) complexes","volume":"33","author":"Firdaus","year":"2008","journal-title":"Trans. Met. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1007\/BF01064247","article-title":"Geometry of New Iron (III) and Copper (II) Azo-Nitroso complexes Trans","volume":"11","author":"Masoud","year":"1986","journal-title":"Met. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"722","DOI":"10.1063\/1.1700523","article-title":"A Molecular Orbital Theory of Reactivity in Aromatic Hydrocarbons","volume":"20","author":"Fukui","year":"1952","journal-title":"J. Chem. Phys."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"988","DOI":"10.1002\/etc.5620170603","article-title":"Molecular orbital calculations to describe microbial reductive dechlorination of polychlorinated dioxins","volume":"17","author":"Lynam","year":"1998","journal-title":"Environ. Toxicol. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1016\/j.compbiolchem.2018.01.007","article-title":"DFT\/TD-DFT calculations, spectroscopic characterizations (FTIR, NMR, UV-vis), molecular docking and enzyme inhibition study of 7-benzoyloxycoumarin","volume":"73","author":"Alam","year":"2018","journal-title":"Comput. Biol. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"227","DOI":"10.1016\/j.ica.2017.08.016","article-title":"Synthesis and characterization of cobalt (II), nickel (II), copper (II) and zinc (II) complexes derived from two Schiff base ligands: Spectroscopic, thermal, magnetic moment, electrochemical and antimicrobial studies","volume":"467","author":"Orojloo","year":"2017","journal-title":"Inorg. Chim. Acta"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1016\/j.poly.2016.05.036","article-title":"Copper(II) and nickel(II) complexes with N\u2032-[(Z)-phenyl(pyridin-2-yl)methylidene]acetohydrazide: Synthesis, crystal structures, DFT calculations and antioxidant effects","volume":"117","author":"Patel","year":"2016","journal-title":"Polyhedron"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1688","DOI":"10.1016\/j.eurpolymj.2013.03.015","article-title":"From metal complexes to metallosupramolecular polymers via polycondensation: Synthesis, structure and electrochromic properties of Co(III)- and Fe(III)-based metallosupramolecular polymers with aromatic azo ligands","volume":"49","author":"Bandyopadhyay","year":"2013","journal-title":"Eur. Polym. J."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"128","DOI":"10.1016\/j.molcata.2009.03.025","article-title":"Iron(III) complexes of bidentate nitrogen ligands as catalysts in reverse atom transfer radical polymerization of styrene","volume":"307","author":"Ferro","year":"2009","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_41","unstructured":"Frisch, M.J. (2009). Gaussian 09, Revision D.01, Gaussian Inc."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"3098","DOI":"10.1103\/PhysRevA.38.3098","article-title":"Density-functional exchange-energy approximation with correct asymptotic behaviour","volume":"38","author":"Beck","year":"1988","journal-title":"Phys. Rev. A"},{"key":"ref_43","first-page":"785","article-title":"Development of the colle-salvetticorrelationenergy formula into a functional of the electron density","volume":"37","author":"Lee","year":"1988","journal-title":"Phys. Rev. A"},{"key":"ref_44","unstructured":"Dennington, R., Keith, T., and Millam, J. (2009). GaussView, Semichem Inc.. Ver. 5."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1002\/(SICI)1096-987X(19990115)20:1<129::AID-JCC13>3.0.CO;2-A","article-title":"Chemical reactivity indexes in density functional theory","volume":"20","author":"Chermette","year":"1999","journal-title":"J. Comput. Chem."},{"key":"ref_46","first-page":"113","article-title":"An antibiotic assay by the agar well diffusion method","volume":"15","author":"Perez","year":"1990","journal-title":"Acta Biol. Med. Exp."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"106","DOI":"10.1002\/jobm.200410355","article-title":"Effect of certain bioactive plant extracts on clinical isolates of beta-lactamase producing methicillin resistant Staphylococcus aureus","volume":"45","author":"Aqil","year":"2005","journal-title":"J. Basic Microbiol."},{"key":"ref_48","unstructured":"Cruickshank, R., Duguid, J.P., Marmion, B.P., and Swain, R.H.A. (1975). Medicinal Microbiology, Churchill Livingstone. [12th ed.]."},{"key":"ref_49","first-page":"91","article-title":"In Vitro antifungal activity of deterium microcarpum","volume":"24","author":"Doughari","year":"2008","journal-title":"Pak. J. Med. Sci."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/23\/4\/813\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T14:59:23Z","timestamp":1760194763000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/23\/4\/813"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,4,2]]},"references-count":49,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2018,4]]}},"alternative-id":["molecules23040813"],"URL":"https:\/\/doi.org\/10.3390\/molecules23040813","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,4,2]]}}}