Abstract
Three different palladium(II) complexes with ligands containing nitrogenized aromatic rings were investigated theoretically as model to obtain the computational band gap energies. The results demonstrated promising possibility for designing palladium(II) complexes with photocatalytic properties at visible light irradiation. Deliberated products were synthesized via grafting on the silica-coated Fe3O4 magnetic nanoparticles (Fe3O4@SiO2). Formation of complexes on the surface of Fe3O4@SiO2, as insoluble and reusable photocatalysts, was proved by Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), thermogravimetric (TGA), X-ray photoelectron spectroscopy (XPS), vibrating sample magnetometer (VSM), transmission electron microscope (TEM), and scanning electron microscopy (SEM) analyses. The trend of the band gap energies of prepared structures was calculated via experimental and theoretical methods. The photocatalytic capability of these nanoparticles was investigated in degradation of 2,4-dichlorophenol by means of HPLC analysis. A tentative reaction mechanism for the formation of intermediates was proposed.
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Abolhosseini Shahrnoy A, Mahjoub AR, Eslami-Moghadam M, Fakhri H (2014) Dichloro (1,10-phenanthroline-5,6-dione) palladium(II) complex supported by mesoporous silica SBA-15 as a photocatalyst for degradation of 2,4-dichlorophenol. J Mol Struct 1076:568–575. https://doi.org/10.1016/j.molstruc.2014.08.024
Abolhosseini Shahrnoy A, Mahjoub AR, Morsali A, Dusek M, Eigner V (2018) Sonochemical synthesis of polyoxometalate based of ionic crystal nanostructure: a photocatalyst for degradation of 2,4-dichlorophenol. Ultrason Sonochem 40(Pt A):174–183. https://doi.org/10.1016/j.ultsonch.2017.07.018
Aghayan H, Mahjoub AR, Khanchi AR (2013) Synthesis and characterization of cesium molybdo vanado phosphate immobilized on platelet SBA-15: an efficient inorganic composite ion-exchanger for gadolinium ion sorption. Appl Surf Sci 274:7–14. https://doi.org/10.1016/j.apsusc.2013.02.005
Balcha A, Yadav OP, Dey T (2016) Photocatalytic degradation of methylene blue dye by zinc oxide nanoparticles obtained from precipitation and sol-gel methods. Environ Sci Pollut Res 23(24):25485–25493. https://doi.org/10.1007/s11356-016-7750-6
Boruah PK, Sharma B, Karbhal I, Shelke MV, Das MR (2017) Ammonia-modified graphene sheets decorated with magnetic Fe3O4 nanoparticles for the photocatalytic and photo-Fenton degradation of phenolic compounds under sunlight irradiation. J Hazard Mater 325:90–100. https://doi.org/10.1016/j.jhazmat.2016.11.023
Benitez FJ, Beltran-Heredia J, Acero JL, Javier Rubio F (2000) Contribution of free radicals to chlorophenols decomposition by several advanced oxidation processes. Chemosphere 41(8):1271–1277. https://doi.org/10.1016/S0045-6535(99)00536-6
Campos-Carrasco A, Bruce M, Reguero M, Masdeu-Bultó AM (2014) Pd(II) complexes with 3,3′-substituted bipyridine ligands: Synthesis, crystal structure, DFT calculations and catalytic studies in compressed carbon dioxide. Inorg Chim Acta 409:285–295. https://doi.org/10.1016/j.ica.2013.09.053
Chu W-K, Wei X-G, Yiu S-M, Ko C-C, Lau K-C (2015) Strongly phosphorescent neutral rhenium(I) isocyanoborato complexes: synthesis, characterization, and photophysical, electrochemical, and computational studies. Chem Eur J 21(6):2603–2612. https://doi.org/10.1002/chem.201405291
Czaplicka M (2004) Sources and transformations of chlorophenols in the natural environment. Sci Total Environ 322(1-3):21–39. https://doi.org/10.1016/j.scitotenv.2003.09.015
Davis EA, Mott NF (1970) Conduction in non-crystalline systems V. Conductivity, optical absorption and photoconductivity in amorphous semiconductors. Philos Mag 22(179):0903–0922. https://doi.org/10.1080/14786437008221061
Deng YH, Wang CC, Hu JH, Yang WL, Fu SK (2005) Investigation of formation of silica-coated magnetite nanoparticles via sol–gel approach. Colloids Surf A Physicochem Eng Asp 262(1-3):87–93. https://doi.org/10.1016/j.colsurfa.2005.04.009
Dey T (2012) Nanotechnology for water purification. Universal Publishers Inc, USA. isbn:9781612336190
Dey T (2006) Polymer-coated magnetic nanoparticles: surface modification and end-functionalization. J Nanosci Nanotechnol 6(8):2479–2483. https://doi.org/10.1166/jnn.2006.534
Eslami MM, Divsalar A, Abolhosseini Shahrnoy A, Saboury AA (2016) Synthesis, cytotoxicity assessment, and interaction and docking of novel palladium(II) complexes of imidazole derivatives with human serum albumin. J Biomolec Struc Dynam 34:1751–1762. https://doi.org/10.1080/07391102.2015.1090345
Fakhri H, Mahjoub AR, Cheshme Khavar AH (2016) Improvement of visible light photocatalytic activity over graphene oxide/CuInS2/ZnO nanocomposite synthesized by hydrothermal method. Mat Sci in Semicon Proc 41:38–44. https://doi.org/10.1016/j.mssp.2015.05.020
Jakonen M, Hirva P, Haukka M, Chardon-Noblat S, Lafolet F, Chauvin J, Deronzier A (2007) An alternative synthesis method for [Os(NN)(CO)2X2] complexes (NN = 2,2′-bipyridine, 4,4′-dimethyl-2,2′-bipyridine; X = Cl, Br, I). Electrochemical and photochemical properties and behavior. Dalton Trans (30):3314–3324. https://doi.org/10.1039/B704931E
Ha K (2010a) Acta Cryst E66:m7
Ha K (2010b) Acta Cryst E66:m38
Ha K (2010c) Acta Cryst E66:m145
Kaya Y, Icsel C, Yilmaz VT, Buyukgungor O (2014) Palladium(II) and platinum(II) complexes of a new imineoxime ligand—structural, spectroscopic and DFT/time-dependent (TD) DFT studies. J Organomet Chem 752:83–90. https://doi.org/10.1016/j.jorganchem.2013.12.011
Kokushi E, Shintoyo A, Koyama J, Uno S (2016) Evaluation of 2,4-dichlorophenol exposure of Japanese medaka, Oryzias latipes, using a metabolomics approach. Environ Sci Pollut Res 24(36):27678–27686. https://doi.org/10.1007/s11356-016-6425-7
Lam SM, Sin JC, Abdullah AZ, Mohamed AR (2012) Degradation of wastewaters containing organic dyes photocatalysed by zinc oxide: a review. Desalinat Water Treatment 41(1-3):131–169. https://doi.org/10.1080/19443994.2012.664698
Laurent S, Forge D, Port M, Roch A, Robic C, Elst LV, Muller RN (2008) Magnetic iron oxide nanoparticles: synthesis, stabilization, vectorization, physicochemical characterizations, and biological applications. Chem Rev 108(6):2064–2110. https://doi.org/10.1021/cr068445e
Lehlooh AF, Mahmood S, Abu-Aljarayesh I (1994) Mössbauer and X-ray diffraction studies of heat-treated Fe3O4 fine particles. J Magn Magn Mater 136:143–148. https://doi.org/10.1016/0304-8853(94)90458-8
Leong KH, Monash P, Ibrahim S, Saravanan P (2014) Solar photocatalytic activity of anatase TiO2 nanocrystals synthesized by non-hydrolitic sol–gel method. Sol Energy 101:321–332. https://doi.org/10.1016/j.solener.2014.01.006
Miranda SM, Lopes FVS, Rodrigues-Silva C, Martins SDS, Silva AMT, Faria JL, Boaventura RAR, Vilar VJP (2015) Solar photocatalytic gas-phase degradation of n-decane—a comparative study using cellulose acetate monoliths coated with P25 or sol-gel TiO2 films. Environ Sci Pollut Res 22(2):820–832. https://doi.org/10.1007/s11356-014-2952-2
Morel AL, Nikitenko SI, Gionnet K, Wattiaux A, Lai-Kee-Him J, Labrugere C, Chevalier B, Deleris G, Petibois C, Brisson A, Simonoff M (2008) Sonochemical approach to the synthesis of Fe3O4@SiO2 core–shell nanoparticles with tunable properties. ACS Nano 2(5):847–856. https://doi.org/10.1021/nn800091q
Nejat R, Mahjoub AR (2016) Magnetically water-dispersible and recoverable rhodium organometallic catalyst derived from Wilkinson’s catalyst for promoting organic reactions. Appl Organometl Chem 31(7). https://doi.org/10.1002/aoc.3657
Nejat R, Chamack M, Mahjoub A (2017) Active and recyclable ordered mesoporous magnetic organometallic catalyst as high-performance visible light photocatalyst for degradation of organic pollutants. Appl Organometal Chem 31(11):e3745. https://doi.org/10.1002/aoc.3745
Pirhayati M, Kakanejadifard A, Veisi H (2016) A new nano-Fe3O4-supported organocatalyst based on 3,4-dihydroxypyridine: an efficient heterogeneous nanocatalyst for one-pot synthesis of pyrazolo[3,4-b]pyridines and pyrano[2,3-d]pyrimidines. Appl Organomet Chem 30(12):1004–1008. https://doi.org/10.1002/aoc.3534
Prasad C, Sreenivasulu K, Gangadhara S, Venkateswarlu P (2017) Bio inspired green synthesis of Ni/Fe3O4 magnetic nanoparticles using Moringa oleifera leaves extract: a magnetically recoverable catalyst for organic dye degradation in aqueous solution, J. Alloys Compd 700:252–258. https://doi.org/10.1016/j.jallcom.2016.12.363
Richard C, Boule P (1991) Oxidizing species involved in transformations on zinc oxide. J Photochem Photobiol A Chem 60(2):235–243. https://doi.org/10.1016/1010-6030(91)85063-M
Taufik A, Saleh R (2017) Synthesis of iron(II,III) oxide/zinc oxide/copper(II) oxide (Fe3O4/ZnO/CuO) nanocomposites and their photosonocatalytic property for organic dye removal. J Colloid Interface Sci 491:27–36. https://doi.org/10.1016/j.jcis.2016.12.018
Yan M, Hua Y, Zhu F, Gu W, Jiang J, Shen H, Shi W (2017) Fabrication of nitrogen doped graphene quantum dots-BiOI/MnNb2O6 p-n junction photocatalysts with enhanced visible light efficiency in photocatalytic degradation of antibiotics. Appl Catal B Environ 202:518–527. https://doi.org/10.1016/j.apcatb.2016.09.039
Zhao D, Huo Q, Feng J, Chmelka BF, Stucky GD (1998) Nonionic triblock and star diblock copolymer and oligomeric surfactant syntheses of highly ordered, hydrothermally stable, mesoporous silica structures. J Am Chem Soc 120(24):6024–6036. https://doi.org/10.1021/ja974025i
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Support of this investigation by Tarbiat Modares University and Iranian nanotechnology initiative council is gratefully acknowledged.
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Tehrani Nejad, S., Abolhosseini Shahrnoy, A., Mahjoub, A.R. et al. Photodegradation of 2,4-dichlorophenol by supported Pd(X2) catalyst (X = Cl, Br, N3): a HOMO manipulating point of view. Environ Sci Pollut Res 25, 9969–9980 (2018). https://doi.org/10.1007/s11356-017-1117-5
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DOI: https://doi.org/10.1007/s11356-017-1117-5