Study of the Degradation of Dyes by a Mononuclear Copper Complex Forming a Zigzag Chain

Article Preview

Abstract:

The titled mononuclear complex [Cu (L)] with the formally tetradentate schiff base ligand, [N,N’-bis (2-hydroxy-3-methoxybenzylidene)-1,3-diaminopropan-2-ol] has been synthesized and characterized using IR spectroscopy and elemental analysis. Crystal structure has been determined by XRD which reveals the pseudo octahedral complex geometry and the use of hydroxo bridges between two neighbor units to form a 1D coordination polymer. The use of this complex as a catalyst for the degradation of two textile dyes, in the presence of the appropriate amount of H2O2 and a UV light source has given very good results with yields exceeding 98% after 50 minutes.

You have full access to the following eBook

Info:

* - Corresponding Author

[1] Sheldon, R., Santen, R. Catalytic oxidation, principles and applications. World Scientific, Singapore. (1995).

Google Scholar

[2] Zamian, J. R, Dockal, E. R., Tetradentate Schiff base oxovanadium(IV)complexes, Trans Met Chem. 21(1996) 370-376.

DOI: 10.1007/bf00139036

Google Scholar

[3] Kolawole, G. A., Patel, K. S, Earnshaw A., the stereochemistry of oxovanadium (IV) complexes derived from substituted 2-hydroxy aromatic aldehydes and aromatic diamines. J. Coord Chem. 14 (1985) 57-63.

DOI: 10.1080/00958978508080678

Google Scholar

[4] Datta, A., Choudhury, C. R., Talukder, P., Mitra, S., Dahlenburg, L., Matsushita, T., A novel doubly phenoxo-bridged Cu(II) trimer: synthesis, crystal structure and low-temperature magnetic behaviour. J. Chem. Research (S). (2003) 642-644.

DOI: 10.3184/030823403322656247

Google Scholar

[5] Thakurta, S., Chakraborty, J., Rosair, G., Tercero, J., El Fallah, M. S., Garribba, E., Mitra, S., Synthesis of Two New Linear Trinuclear CuII Complexes: Mechanism of Magnetic Coupling through Hybrid B3LYP Functional and CShM Studies. Inorg. Chem. 47 (2008) 6227-6235.

DOI: 10.1021/ic8001459

Google Scholar

[6] Talukder, P., Shit, S., Sasmal, A., Batten, S. R., Moubaraki, B., Murray, K.S., Mitra, S., An antiferromagnetically coupled hexanuclear copper(II) Schiff base complex containing phenoxo and dicyanamido bridges: Structural aspects and magnetic properties. Polyhedron. 30 (2011) 1767-1773.

DOI: 10.1016/j.poly.2011.03.049

Google Scholar

[7] Costes, J. P., Duhayon, C., Vendier, L., Mota, A. J., Reaction of a series of ZnL, CuL and NiL Schiff base and non-Schiff base complexes with MCl2 salts (M = Cu, Ni, Mn). Syntheses, structures, magnetic properties and DFT calculations. New J. Chem. 42 (2018) 3683.

DOI: 10.1039/c7nj04347c

Google Scholar

[8] Parsekar, S. U., Paliwal, K., Haldar, P., Sudhadevi Antharjanam, P. K. Kumar, M., Synthesis, Characterization, Crystal Structure, DNA and HSA Interactions, and Anticancer Activity of a Mononuclear Cu(II) Complex with a Schiff Base Ligand Containing a Thiadiazoline Moiety. ACS Omega. 7 (2022) 2881-2896.

DOI: 10.1021/acsomega.1c05750

Google Scholar

[9] Hui Yang, Shan-Shan Liu, Yin-Shan Meng, Yi-Quan Zhang, Lin Pu, Xincheng Wang, Shijing Lin., Four mononuclear dysprosium complexes with neutral Schiff-base ligands: syntheses, crystal structures and slow magnetic relaxation behavior . Dalton Trans. 51 (2022) 1415-1422.

DOI: 10.1039/d1dt03701c

Google Scholar

[10] Chiboub Fellah, F. Z., Duhayon, C., Mallet-Ladeira, S., Vendier, L., Costes, J. P., Cu-Ln complexes involving non-symmetrical ligands able to introduce asymmetric centres in the vicinity of Ln ions. Polyhedron. 224 (2022) 116015.

DOI: 10.1016/j.poly.2022.116015

Google Scholar

[11] Chiboub Fellah, F. Z. Pointillart, F. Guizouarn, T. Roisnel, T. Dege, N. Chiboub Fellah, A. Hassaine R., Photophysical Properties and Single-Molecule Magnet Behavior in Heterobimetallic 3d4 f Schiff Base Complexes . European Journal of Inorganic Chemistry. 27 (2022).

DOI: 10.1002/ejic.202200349

Google Scholar

[12] Novitchi, G., Shova, S., Caneschi, A., Costes, J. P., Gdaniec, M., Stanica. N., Hetero di- and trinuclear Cu–Gd complexes with trifluoroacetate bridges: synthsis, structural and magnetic studies. Dalton Trans. (2004) 1194-1200.

DOI: 10.1039/b312186k

Google Scholar

[13] Chiboub Fellah, F. Z., Costes, J.P., Dahan, F., Duhayon, C., Tuchagues, J. P., Varying the metal/metal ratio in related Cu–Ca complexes. Polyhedron. 26 (2007) 4209.

DOI: 10.1016/j.poly.2007.05.019

Google Scholar

[14] Costes, J-P., Dahan, F., Laurent, J-P., A Monomeric, Self-Assembling, Alkali-Metal Binding Nickel Complex: Reappraisal of the Original Model from Solid-State and Solution Studies Inorg. Chem. 33 (1994) 2738.

DOI: 10.1021/ic00091a012

Google Scholar

[15] Butsch, K., Gunther, T.,A.Klein, Stirnat, K., Berkessel, A., Neudorfl. J., Redox chemistry of copper complexes with various salen type ligands. Inorganica. Chimica. Acta. 394 (2012) 237-246.

DOI: 10.1016/j.ica.2012.08.016

Google Scholar

[16] Gupta, K.C., Sutar. A.K., Catalytic activity of polymer anchored N,N'-bis ( o-hydroxy acetophenone) ethylene diamine Schiff base complexes of Fe(III), Cu(II) and Zn(II) ions in oxidation of phenol. Reactive & Functional Polymers. 68 (2008) 12–26.

DOI: 10.1016/j.reactfunctpolym.2007.10.015

Google Scholar

[17] Chiboub Fellah, F.Z., Costes, J-P., Dahan, F., Duhayon, C., Novitchi, G., Tuchagues, J-P., Vendier. L., Di- and Triheteronuclear Cu−Gd and Cu−Gd−Cu Complexes with Dissymmetric Double Bridge. Inorg. Chem. 47 (2008) 6444.

DOI: 10.1021/ic800599r

Google Scholar

[18] Chiboub Fellah, F.Z., Costes, J-P., Duhayon, C., Daran, J-C., Tuchagues. J-P., Mononuclear Cu and dinuclear Cu–Ln complexes of benzimidazole based ligands including N and O donors: Syntheses, characterization, X-ray molecular structures and magnetic properties. Polyhedron. 29 (2010) 2111-2119.

DOI: 10.1016/j.poly.2010.04.010

Google Scholar

[19] Sarkar, S., Biswas, S., Dey. K., Synthesis, spectroscopic characterization and magnetic properties of homo- and heterodinuclear complexes of transition and non-transition metal ions with a new Schiff base ligand. Spectrochimica. Acta. Part A. 71 (2008) 1555-1561.

DOI: 10.1016/j.saa.2008.06.002

Google Scholar

[20] Sain, S., Saha, R., Mostafa, G., Fleck, M., Bandyopadhyay, D., Synthesis and crystal structure of three new copper(II) complexes with a tridentate amine and its Schiff bases. Polyhedron. 31 (2012) 82-88.

DOI: 10.1016/j.poly.2011.08.040

Google Scholar

[21] Omidi, S., Kakanejadifard,A., A review on biological activities of Schiff base, hydrazone, and oxime derivatives of curcumin . RSC Adv. 10 (2020) 30186-30202.

DOI: 10.1039/d0ra05720g

Google Scholar

[22] Yogesh Deswal, Sonika Asija, Amit Dubey, Laxmi Deswal, Deepak Kumar, DeepakKumar Jindal, Jai Devi., Cobalt(II), nickel(II), copper(II) and zinc(II) complexes of thiadiazole based Schiff base ligands: Synthesis, structural characterization, DFT, antidiabetic and molecular docking studies. Journal of Molecular Structure. 1253 (2022) 132266.

DOI: 10.1016/j.molstruc.2021.132266

Google Scholar

[23] Mazurek, W., Kennedy, B.J., Murray, K.S., O'Connor, M.J., Rodgers, J.R., Snow, M.R., Wedd, A.G. & Zwack, P.R., Magnetic interactions in metal complexes of binucleating ligands. 2. Synthesis and properties of binuclear copper(II) compounds containing exogenous ligands that bridge through two atoms. Crystal and molecular structure of a binuclear .mu.-pyrazolato-N,N'-bridged dicopper(II) complex of 1,3-bis(salicylideneamino)propan-2-ol. lnorg. Chem. 24 (1985) 3258-3264.

DOI: 10.1021/ic00214a033

Google Scholar

[24] Nishida, Y., Kida, S., Crystal structures and magnetism of binuclear copper (II) complexes with alkoxide bridges. Importance of orbital complementarity in spin coupling through two different bridging groups. J. Chem. Soc., Dalton Trans. (1986) 2633-2640.

DOI: 10.1039/dt9860002633

Google Scholar

[25] Singh, K, Siwach, P., Synthesis, spectroscopic, theoretical and biological evaluation of novel Schiff base complexes of divalent transition metals Applied Organometallic Chemistry. 36 (2022) 6553.

DOI: 10.1002/aoc.6553

Google Scholar

[26] Smith, K. I., Borer, L. L., Olmstead, M. M., Vanadium (IV) and Vanadium (V) Complexes of Salicyladimine Ligands . Inorg. Chem. 42 (2003) 7410-7415

DOI: 10.1021/ic034640p

Google Scholar

[27] Manna, S., Zangrando, E., Manna, S. C., Schiff base and azido coordinated di-/poly-nuclear cadmium(II) complexes: Crystal structure, photocatalytic degradation of methylene blue and thermal analysis. Polyhedron. 177 (2020) 114296.

DOI: 10.1016/j.poly.2019.114296

Google Scholar

[28] Manimohan, M., Pugalmani, S., K. Ravichandran, Sithique, M.A., Synthesis and characterisation of novel Cu(II )-anchored biopolymer complexes as reusable materials for the photocatalytic degradation of methylene blue . RSC Adv. 10 (2020) 18259-18279

DOI: 10.1039/d0ra01724h

Google Scholar

[29] Basak, T., Bhattacharyya, A., Harms, K., Chattopadhyay, S., The ability of a trinuclear zinc(II) Schiff base complex to act as a photocatalyst for the degradation of methylene blue and to mimic phosphatase. Polyhedron. 157 (2019) 449-457.

DOI: 10.1016/j.poly.2018.09.070

Google Scholar

[30] Fathima Fasna, P. H., Sasi, S., Sharmila, B., Julie Chandra, T. K., Antony, C. S., Raman, J. V., Photocatalytic remediation of methylene blue and antibacterial activity study using Schiff base-Cu complexes. Environmental Science and Pollution Research. 29 (2022) 54318-54329.

DOI: 10.1007/s11356-022-19694-x

Google Scholar

[31] Xu-Jia Hong., Xiang Liu., Jing-Bo Zhang., Chu-Ling Lin., Xiao Wu., Yan-Jun Ou., Jian Yang., Hong-Guang Jin., Yue-Peng Cai., Two low-dimensional Schiff base copper(i/ii) complexes: synthesis, characterization and catalytic activity for degradation of organic dyes. CrystEngComm. 16 (2014) 7926-7932.

DOI: 10.1039/c4ce01207k

Google Scholar

[32] Bhaumik, P. K., Chattopadhyay, S., Synthetic methodology, structures and properties of mixed valence copper (I/II) complexes with various Schiff bases and their reduced analogues. Polyhedron. 199 (2021) 115086.

DOI: 10.1016/j.poly.2021.115086

Google Scholar

[33] Hu Wang., Xiao-Yin Zhang., Cai-Feng Bi., Yu-Hua Fan., Xiang-Min Meng., Hu Wang, Xiao-Yin Zhang, Cai-Feng Bi, Yu-Hua Fan, Xiang-Min Meng, Synthesis, crystal structures and photocatalytic properties of Zn(II), Ni(II), Co(II) complexes with a symmetric open-chain N2O4-donor bis-Schiff base ligand. Transition Met Chem. 40 (2015) 769–777.

DOI: 10.1007/s11243-015-9975-5

Google Scholar

[34] Hu. Wang., Xiangmin. Meng., Chuanbin Fan., Yuhua Fan., Caifeng Bi., Synthesis, crystal structure, DFT study and photocatalytic property of a new Ni(II) complex of a symmetric N2O4-donor bis-Schiff base ligand. Journal of Molecular Structure. 1107 (2016) 25-30.

DOI: 10.1016/j.molstruc.2015.11.035

Google Scholar

[35] Carvalho, S. S. F., Rodrigues, A. C. C., Lima, J.F., Carvalho N. M.F., Photocatalytic degradation of dyes by mononuclear copper(II) complexes from bis-(2-pyridylmethyl)amine NNN-derivative ligands. Inorganica Chimica Acta 512 (2020) 119924.

DOI: 10.1016/j.ica.2020.119924

Google Scholar

[36] Sheldrick, G. M., SHELXT - Integrated space-group and crystal-structure determination. Acta Crystallogr. Sect. A. Found. Crystallogr. 71 (2015) 3-8.

DOI: 10.1107/s2053273314026370

Google Scholar

[37] Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. Sect. C. Struct. Chem. 71 (2015) 3-8.

DOI: 10.1107/s2053229614024218

Google Scholar

[38] Nakamoto, K., Infrared and Raman Spectra of Inorganic and Coordination Compounds, Parts A and B, 5th ed. JohnWiley, New York, (1997).

Google Scholar

[39] Temel . H., Sekerci, M., novel complexes of manganese (III), cobalt (II), copper (II), and zinc (II) with schiff base derived from 1,2-bis(p-aminophenoxy)ethane and salicylaldehyde. synth. react. inorg. met-org. chem. 31(2001) 849-857.

DOI: 10.1081/sim-100104855

Google Scholar

[40] Turan, N., sekerci, M., Synthesis and Characterization of Co(II), Ni(II), Cu(II) and Cd(II)Complexes of Schiff Base Derived from 1,8-Diaminonaphthalene. Asian J. Chem. 21(2009), 6939-6944.

DOI: 10.14233/ajchem.2013.13322

Google Scholar

[41] Palaniappan, M., Selvaraj, D., Kandasamy, H., Kahng , S.Y., Narayanan , M., Rajendran , R., Rangappan, R., Architectural MCM 41 was anchored to the Schiff base Co(II) complex to enhance methylene blue dye degradation and mimic activity. Environmental Research. 215 (2022) 114325.

DOI: 10.1016/j.envres.2022.114325

Google Scholar

[42] Bhaskar, S., Jha, P., Subramaniam, C., Ramamurthy, S. S., Multifunctional hybrid soret nanoarchitectures for mobile phone-based picomolar Cu2+ ion sensing and dye degradation applications. Physica E. 132 (2021) 114764.

DOI: 10.1016/j.physe.2021.114764

Google Scholar