Enhanced debromination of 2,2′,4,4′-tetrabromodiphenyl ether (BDE-47) by zero-valent zinc with ascorbic acid

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Frontiers of Environmental Science & Engineering ›› 2020, Vol. 14 ›› Issue (3) : 47. DOI: 10.1007/s11783-020-1224-2
RESEARCH ARTICLE

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Enhanced debromination of 2,2′,4,4′-tetrabromodiphenyl ether (BDE-47) by zero-valent zinc with ascorbic acid

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Highlight

• Highly efficient debromination of BDE-47 was achieved in the ZVZ/AA system.

• BDE-47 debromination by the ZVZ/AA can be applied to a wide range of pH.

• AA inhibits the formation of (hydr)oxide and accelerates the corrosion of ZVZ.

• Reduction mechanism of BDE-47 debromination by the ZVZ/AA system was proposed.

Abstract

A new technique of zero-valent zinc coupled with ascorbic acid (ZVZ/AA) was developed and applied to debrominate the 2,2′,4,4′-Tetrabromodiphenyl ether (BDE-47), which achieved high conversion and rapid debromination of BDE-47 to less- or non-toxic forms. The reaction conditions were optimized by the addition of 100 mg/L ZVZ particles and 3 mmol/L AA at original solution pH= 4.00 using the solvent of methanol/H2O (v:v= 4:6), which could convert approximately 94% of 5 mg/L BDE-47 into lower-brominated diphenyl ethers within a 90 min at the ZVZ/AA system. The high debromination of BDE-47 was mainly attributed to the effect of AA that inhibits the formation of Zn(II)(hydr)oxide passivation layers and promotes the corrosion of ZVZ, which leads to increase the reactivity of ZVZ. Additionally, ion chromatography and gas chromatography mass spectrometry analyses revealed that bromine ion and lower-debromination diphenyl ethers formed during the reduction of BDE-47. Furthermore, based on the generation of the intermediates products, and its concentration changes over time, it was proposed that the dominant pathway for conversion of BDE-47 was sequential debromination and the final products were diphenyl ethers. These results suggested that the ZVZ/AA system has the potential for highly efficient debromination of BDE-47 from wastewater.

Keywords

2,2′,4,4′-tetrabromodiphenyl ether (BDE-47) / Ascorbic acid / Reductive debromination / Zero-valent zinc

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. . Frontiers of Environmental Science & Engineering. 2020, 14(3): 47 https://doi.org/10.1007/s11783-020-1224-2

参考文献

[1]
Abdallah M A, Pawar G, Harrad S (2015). Effect of bromine substitution on human dermal absorption of polybrominated diphenyl ethers. Environmental Science & Technology, 49(18): 10976–10983
CrossRef ADS Google scholar
[2]
Ahmad H B, Abbas Y, Hussain M, Akhtar N, Ansari T M, Zuber M, Zia K M, Arain S A (2014). Synthesis and application of alumina supported nano zero valent zinc as adsorbent for the removal of arsenic and nitrate. Korean Journal of Chemical Engineering, 31(2): 284–288
CrossRef ADS Google scholar
[3]
Al-Harahsheh M, Aljarrah M, Al-Otoom A, Altarawneh M, Kingman S (2018). Pyrolysis kinetics of tetrabromobisphenol a (TBBPA) and electric arc furnace dust mixtures. Thermochimica Acta, 660: 61–69
CrossRef ADS Google scholar
[4]
Blotevogel J, Giraud R J, Borch T (2018). Reductive defluorination of perfluorooctanoic acid by zero-valent iron and zinc: A DFT-based kinetic model. Chemical Engineering Journal, 335: 248–254
CrossRef ADS Google scholar
[5]
Boronina T N, Dieken L, Lagadic I, Klabunde K J (1998). Zinc-silver, zinc-palladium, and zinc-gold as bimetallic systems for carbon tetrachloride dechlorination in water. Journal of Hazardous Substance Research, 1(1): 7
CrossRef ADS Google scholar
[6]
Cao H, He M, Han D, Li J, Li M, Wang W, Yao S (2013). OH-initiated oxidation mechanisms and kinetics of 2,4,4′-Tribrominated diphenyl ether. Environmental Science & Technology, 47(15): 8238–8247
CrossRef ADS Google scholar
[7]
Chen J, Wang C, Pan Y, Farzana S S, Tam N F Y (2018). Biochar accelerates microbial reductive debromination of 2,2',4,4'-tetrabromodiphenyl ether (BDE-47) in anaerobic mangrove sediments. Journal of Hazardous Materials, 341: 177–186
CrossRef ADS Google scholar
[8]
Choi J H, Kim Y H (2009). Reduction of 2,4,6-trichlorophenol with zero-valent zinc and catalyzed zinc. Journal of Hazardous Materials, 166(2–3): 984–991
CrossRef ADS Google scholar
[9]
Chung S S, Zheng J S, Kwong A C S, Lai V W Y (2018). Harmful flame retardant found in electronic cigarette aerosol. Journal of Cleaner Production, 171: 10–16
CrossRef ADS Google scholar
[10]
Djedidi Z, Médard B, Cheikh R B, Mercier G, Tyagi R D, Blais J F (2009). Comparative study of dewatering characteristics of metal precipitates generated during treatment synthetic polymetallic and AMD solutions. Hydrometallurgy, 98(3–4): 247–256
CrossRef ADS Google scholar
[11]
Fang L, Xu L, Li J, Huang L Z (2019). Copper nanoparticles/graphene modified green rusts for debromination of tetrabromobisphenol A: Enhanced galvanic effect, electron transfer and adsorption. Science of the Total Environment, 683: 275–283
CrossRef ADS Google scholar
[12]
Fang Z, Qiu X, Chen J, Qiu X (2011). Debromination of polybrominated diphenyl ethers by Ni/Fe bimetallic nanoparticles: Influencing factors, kinetics, and mechanism. Journal of Hazardous Materials, 185(2–3): 958–969
CrossRef ADS Google scholar
[13]
Fu Z, Wang Y, Chen J, Wang Z, Wang X (2016). How PBDEs are transformed into dihydroxylated and dioxin metabolites catalyzed by the active center of cytochrome P450s: A DFT study. Environmental Science & Technology, 50(15): 8155–8163
CrossRef ADS Google scholar
[14]
Fukuchi S, Nishimoto R, Fukushima M, Zhu Q (2014). Effects of reducing agents on the degradation of 2,4,6-tribromophenol in a heterogeneous Fenton-like system with an iron-loaded natural zeolite. Applied Catalysis B: Environmental, 147: 411–419
CrossRef ADS Google scholar
[15]
Gao X, Yang F, Lan Y, Mao J D, Duan X (2011). Rapid degradation of carbon tetrachloride by commercial micro-scale zinc powder assisted by citric acid. Environmental Chemistry Letters, 9(3): 431–438
CrossRef ADS Google scholar
[16]
Gómara B, Herrero L, Ramos J J, Mateo J R, Fernandez M A, Garcia J F, Gonzalez M J (2007). Distribution of polybrominated diphenyl ethers in human umbilical. cord serum, paternal serum, maternal serum, placentas, and breast milk from Madrid population, Spain. Environmental Science & Technology, 41(20): 6961–6968
CrossRef ADS Google scholar
[17]
Guo J, Jiang D, Wu Y, Zhou P, Lan Y (2011). Degradation of methyl orange by Zn0 assisted with silica gel. Journal of Hazardous Materials, 194: 290–296
CrossRef ADS Google scholar
[18]
Guo J, Li Y, Dai R, Lan Y (2012). Rapid reduction of Cr(VI) coupling with efficient removal of total chromium in the coexistence of Zn0 and silica gel. Journal of Hazardous Materials, 243: 265–271
CrossRef ADS Google scholar
[19]
Han Y, Chen Z L, Tong L N, Yang L, Shen J M, Wang B Y, Liu Y, Liu Y, Chen Q (2013). Reduction of N-Nitrosodimethylamine with zero-valent zinc. Water Research, 47(1): 216–224
CrossRef ADS Google scholar
[20]
He J, Robrock K R, Alvarez-Cohen L (2006). Microbial reductive debromination of polybrominated diphenyl ethers (PBDEs). Environmental Science & Technology, 40(14): 4429–4434
CrossRef ADS Google scholar
[21]
Hites R A, Foran J A, Schwager S J, Knuth B A, Hamilton M C, Carpenter D O (2004). Global assessment of polybrominated diphenyl ethers in farmed and wild salmon. Environmental Science & Technology, 38(19): 4945–4949
CrossRef ADS Google scholar
[22]
Hou X, Shen W, Huang X, Ai Z, Zhang L (2016). Ascorbic acid enhanced activation of oxygen by ferrous iron: a case of aerobic degradation of rhodamine B. Journal of Hazardous Materials, 308: 67–74
CrossRef ADS Google scholar
[23]
Huang J, Wang X, Long Q, Wen X, Zhou Y, Li L (2009). Influence of pH on the stability characteristics of nanofluids. In: 2009 Symposium on Photonics and Optoelectronics. Washington, DC: IEEE, 1–4
[24]
Jeyaraju P (2007). Determination of Vitamin C (Ascorbic Acid) Content in Vitamin C Supplements by Redox Titration. Dissertation for the Doctoral Degree. Sabah: Universiti Malaysia Sabah
[25]
Keum Y S, Li Q X (2005). Reductive debromination of polybrominated diphenyl ethers by zerovalent iron. Environmental Science & Technology, 39(7): 2280–2286
CrossRef ADS Google scholar
[26]
Kim M, Guerra P, Theocharides M, Barclay K, Smyth S A, Alaee M (2013). Parameters affecting the occurrence and removal of polybrominated diphenyl ethers in twenty Canadian wastewater treatment plants. Water Research, 47(7): 2213–2221
CrossRef ADS Google scholar
[27]
Kleszczewska E (1999). The spectrophotometry determination of chelate complex: L-ascorbic acid with cuprum (ii) and mercury (ii) in alkaline solution. Polish Journal of Environmental Studies, 8: 313–318
[28]
Li A, Tai C, Zhao Z, Wang Y, Zhang Q, Jiang G, Hu J (2007). Debromination of decabrominated diphenyl ether by resin-bound iron nanoparticles. Environmental Science & Technology, 41(19): 6841–6846
CrossRef ADS Google scholar
[29]
Li W, Chen C, Zhu J, Zhou L, Lan Y (2019a). Efficient removal of aniline by micro-scale zinc-copper (mZn/Cu) bimetallic particles in acidic solution: An oxidation degradation mechanism via radicals. Journal of Hazardous Materials, 366: 482–491
CrossRef ADS Google scholar
[30]
Li X, Wang P, Feng C, Liu D, Chen J, Wu F (2019b). Acute toxicity and hazardous concentrations of zinc to native freshwater organisms under different pH values in China. Bulletin of Environmental Contamination and Toxicology, 103(1): 120–126
CrossRef ADS Google scholar
[31]
Liang C, Lin Y T, Shiu J W (2016). Reduction of nitrobenzene with alkaline ascorbic acid: Kinetics and pathways. Journal of Hazardous Materials, 302: 137–143
CrossRef ADS Google scholar
[32]
Lin Y T, Liang C (2013). Carbon tetrachloride degradation by alkaline ascorbic acid solution. Environmental Science & Technology, 47(7): 3299–3307
CrossRef ADS Google scholar
[33]
Lin Y T, Liang C (2015). Reductive dechlorination of carbon tetrachloride using buffered alkaline ascorbic acid. Chemosphere, 136: 27–31
CrossRef ADS Google scholar
[34]
Liu Z, Gu C, Ye M, Bian Y, Cheng Y, Wang F, Yang X, Song Y, Jiang X (2015). Debromination of polybrominated diphenyl ethers by attapulgite-supported Fe/Ni bimetallic nanoparticles: Influencing factors, kinetics and mechanism. Journal of Hazardous Materials, 298: 328–337
CrossRef ADS Google scholar
[35]
Luo S, Yang S, Xue Y, Liang F, Sun C (2011). Two-stage reduction/subsequent oxidation treatment of 2,2′,4,4′-tetrabromodiphenyl ether in aqueous solutions: Kinetic, pathway and toxicity. Journal of Hazardous Materials, 192(3): 1795–1803
CrossRef ADS Google scholar
[36]
Lyche J L, Rosseland C, Berge G, Polder A (2015). Human health risk associated with brominated flame-retardants (BFRs). Environment International, 74: 170–180
CrossRef ADS Google scholar
[37]
Mecozzi R, Di Palma L, Pilone D, Cerboni L (2006). Use of EAF dust as heterogeneous catalyst in Fenton oxidation of PCP contaminated wastewaters. Journal of Hazardous Materials, 137(2): 886–892
CrossRef ADS Google scholar
[38]
Moreira Bastos P, Eriksson J, Vidarson J, Bergman A (2008). Oxidative transformation of polybrominated diphenyl ether congeners (PBDEs) and of hydroxylated PBDEs (OH-PBDEs). Environmental Science and Pollution Research International, 15(7): 606–613
CrossRef ADS Google scholar
[39]
Mukherjee R, Kumar R, Sinha A, Lama Y, Saha A K (2016). A review on synthesis, characterization, and applications of nano zero valent iron (nZVI) for environmental remediation. Critical Reviews in Environmental Science and Technology, 46(5): 443–466
CrossRef ADS Google scholar
[40]
Nasuha N, Ismail S, Hameed B H (2017). Activated electric arc furnace slag as an effective and reusable Fenton-like catalyst for the photodegradation of methylene blue and acid blue 29. Journal of Environmental Management, 196: 323–329
CrossRef ADS Google scholar
[41]
Rivero-Huguet M, Marshall W D (2009). Influence of various organic molecules on the reduction of hexavalent chromium mediated by zero-valent iron. Chemosphere, 76(9): 1240–1248
CrossRef ADS Google scholar
[42]
Salter-Blanc A J, Tratnyek P G (2011). Effects of solution chemistry on the dechlorination of 1,2,3-trichloropropane by zero-valent zinc. Environmental Science & Technology, 45(9): 4073–4079
CrossRef ADS Google scholar
[43]
Santos M S F, Alves A, Madeira L M (2016). Chemical and photochemical degradation of polybrominated diphenyl ethers in liquid systems: A review. Water Research, 88: 39–59
CrossRef ADS Google scholar
[44]
Sayilgan E, Kukrer T, Yigit N, Civelekoglu G, Kitis M (2010). Acidic leaching and precipitation of zinc and manganese from spent battery powders using various reductants. Journal of Hazardous Materials, 173(1–3): 137–143
CrossRef ADS Google scholar
[45]
Schwertmann U (1991). Solubility and dissolution of iron oxides. Plant and Soil, 130(1–2): 1–25
CrossRef ADS Google scholar
[46]
Sellström U, Kierkegaard A, De Wit C, Jansson B (1998). Polybrominated diphenyl ethers and hexabromocyclododecane in sediment and fish from a Swedish River. Environmental Toxicology and Chemistry, 17(6): 1065–1072
CrossRef ADS Google scholar
[47]
Shi J, Qu R, Feng M, Wang X, Wang L, Yang S, Wang Z (2015). Oxidative degradation of decabromodiphenyl ether (BDE 209) by potassium permanganate: reaction pathways, kinetics, and mechanisms assisted by density functional theory calculations. Environmental Science & Technology, 49(7): 4209–4217
CrossRef ADS Google scholar
[48]
Sjodin A (2003). A review on human exposure to brominated flame retardants?particularly polybrominated diphenyl ethers. Environment International, 29(6): 829–839
CrossRef ADS Google scholar
[49]
Soltermann F, Abegglen C, Tschui M, Stahel S, Von Gunten U (2017). Options and limitations for bromate control during ozonation of wastewater. Water Research, 116: 76–85
CrossRef ADS Google scholar
[50]
Song H, Carraway E R, Kim Y H, Batchelor B, Jeon B H, Kim J G (2008). Amendment of hydroxyapatite in reduction of tetrachloroethylene by zero-valent zinc: Its rate enhancing effect and removal of Zn(II). Chemosphere, 73(9): 1420–1427
CrossRef ADS Google scholar
[51]
Song W L, Ford J C, Li A, Mills W J, Buckley D R, Rockne K J (2004). Polybrominated diphenyl ethers in the sediments of the great lakes. 1. Lake superior. Environmental Science & Technology, 38(12): 3286–3293
CrossRef ADS Google scholar
[52]
Stiborova H, Vrkoslavova J, Pulkrabova J, Poustka J, Hajslova J, Demnerova K (2015). Dynamics of brominated flame retardants removal in contaminated wastewater sewage sludge under anaerobic conditions. Science of the Total Environment, 533: 439–445
CrossRef ADS Google scholar
[53]
Stone A T, Morgan J J (1984). Reduction and dissolution of manganese(III) and manganese(IV) oxides by organics: 2. Survey of the reactivity of organics. Environmental Science & Technology, 18(8): 617–624
CrossRef ADS Google scholar
[54]
Sun C, Zhao D, Chen C, Ma W, Zhao J (2009). TiO2-mediated photocatalytic debromination of decabromodiphenyl ether: kinetics and intermediates. Environmental Science & Technology, 43(1): 157–162
CrossRef ADS Google scholar
[55]
Tomy G, Tittlemier S, Braekevelt E, Halldorson T, Stern G (2001).The physico-chemical properties of some brominated flame retardants. In: First International Workshop on Brominated Flames Retardants, Stockholm, Sweden. Stockholm: Stockholm University
[56]
Vonderheide A P, Mueller K E, Meija J, Welsh G L (2008). Polybrominated diphenyl ethers: Causes for concern and knowledge gaps regarding environmental distribution, fate and toxicity. Science of the Total Environment, 400(1–3): 425–436
CrossRef ADS Google scholar
[57]
Wang C, Lin Z, Dong Q, Lin Z, Lin K, Wang J, Huang J, Huang X, He Y, Huang C, Yang D, Huang C (2012). Polybrominated diphenyl ethers (PBDEs) in human serum from Southeast China. Ecotoxicology and Environmental Safety, 78: 206–211
CrossRef ADS Google scholar
[58]
Wang R, Lu G, Lin H, Huang K, Tang T, Xue X, Yang X, Yin H, Dang Z (2017). Relative roles of H-atom transfer and electron transfer in the debromination of polybrominated diphenyl ethers by palladized nanoscale zerovalent iron. Environmental Pollution, 222: 331–337
CrossRef ADS Google scholar
[59]
Wang R, Tang T, Lu G, Huang K, Chen M, Tao X, Yin H, Dang Z (2018a). Formation and degradation of polybrominated dibenzofurans (PBDFs) in the UV photolysis of polybrominated diphenyl ethers (PBDEs) in various solutions. Chemical Engineering Journal, 337: 333–341
CrossRef ADS Google scholar
[60]
Wang R, Tang T, Xie J, Tao X, Huang K, Zou M, Yin H, Dang Z, Lu G (2018b). Debromination of polybrominated diphenyl ethers (PBDEs) and their conversion to polybrominated dibenzofurans (PBDFs) by UV light: Mechanisms and pathways. Journal of Hazardous Materials, 354: 1–7
CrossRef ADS Google scholar
[61]
Wang X, Du Y, Liu H, Ma J(2018c). Ascorbic acid/Fe0 composites as an effective persulfate activator for improving the degradation of rhodamine B. RSC Advances, 8(36): 20275–20276
CrossRef ADS Google scholar
[62]
Wang X,Lian W, Sun X, Ma J, Ning P (2018d). Immobilization of NZVI in polydopamine surface-modified biochar for adsorption and degradation of tetracycline in aqueous solution. Frontiers of Environmental Science & Engineering, 12(4): 9
[63]
Watanabe I (2003). Environmental release and behavior of brominated flame retardants. Environment International, 29(6): 665–682
CrossRef ADS Google scholar
[64]
Wei G, Zhang J, Luo J, Xue H, Huang D,Cheng Z, Jiang X (2019). Nanoscale zero-valent iron supported on biochar for the highly efficient removal of nitrobenzene. Frontiers of Environmental Science & Engineering, 13(4): 61
[65]
Wu D, Song K, Fang Z, Long Gu F (2013). Theoretical investigation on debromination model of deca-bromodiphenyl ester (BDE209). Current Physical Chemistry, 3(2): 179–186
CrossRef ADS Google scholar
[66]
Wu J, Yi Y, Li Y, Fang Z, Tsang E P (2016). Excellently reactive Ni/Fe bimetallic catalyst supported by biochar for the remediation of decabromodiphenyl contaminated soil: Reactivity, mechanism, pathways and reducing secondary risks. Journal of Hazardous Materials, 320: 341–349
CrossRef ADS Google scholar
[67]
Xue X, Hanna K, Despas C, Wu F, Deng N (2009). Effect of chelating agent on the oxidation rate of PCP in the magnetite/H2O2 system at neutral pH. Journal of Molecular Catalysis A. Chemical, 311(1–2): 29–35
CrossRef ADS Google scholar
[68]
Yang B, Deng J, Wei L, Han Y, Yu G, Deng S, Zhu C, Duan H, Zhuo Q (2018). Synergistic effect of ball-milled Al micro-scale particles with vitamin B12 on the degradation of 2,2′,4,4′-tetrabromodiphenyl ether in liquid system. Chemical Engineering Journal, 333: 613–620
CrossRef ADS Google scholar
[69]
Yang B, Yu G, Huang J (2007). Electrocatalytic hydrodechlorination of 2, 4, 5-trichlorobiphenyl on a palladium-modified nickel foam cathode. Environmental Science & Technology, 41(21): 7503–7508
CrossRef ADS Google scholar
[70]
Yin W, Zhang Y, Wang P, Zheng S, Zhu C, Han X, Zhang Q, Liang Y, Jiang G (2018). Distribution of polybrominated diphenyl ethers (PBDEs) in feather and muscle of the birds of prey from Beijing, China. Ecotoxicology and Environmental Safety, 165: 343–348
CrossRef ADS Google scholar
[71]
Zezza D, Tait S, Della Salda L, Amorena M, Merola C, Perugini M (2019). Toxicological, gene expression and histopathological evaluations of environmentally realistic concentrations of polybrominated diphenyl ethers PBDE-47, PBDE-99 and PBDE-209 on zebrafish embryos. Ecotoxicology and Environmental Safety, 183: 109566
CrossRef ADS Google scholar
[72]
Zhai C, Peng S, Yang L, Wang Q (2014). Evaluation of BDE-47 hydroxylation metabolic pathways based on a strong electron-withdrawing pentafluorobenzoyl derivatization gas chromatography/electron capture negative ionization quadrupole mass spectrometry. Environmental Science & Technology, 48(14): 8117–8126
CrossRef ADS Google scholar
[73]
Zhang M, Lu J, Xu Z, He Y, Zhang B, Jin S, Boman B (2015). Removing polybrominated diphenyl ethers in pure water using Fe/Pd bimetallic nanoparticles. Frontiers of Environmental Science & Engineering, 9(5): 832–839
[74]
Zhang X, Gu X, Lu S, Brusseau M L, Xu M, Fu X, Qiu Z, Sui Q (2017). Application of ascorbic acid to enhance trichloroethene degradation by Fe(III)-activated calcium peroxide. Chemical Engineering Journal, 325: 188–198
CrossRef ADS Google scholar
[75]
Zhao C, Yan M, Zhong H, Liu Z, Shi L, Chen M, Zeng G, Song B, Shao B, Feng H (2018). Biodegradation of polybrominated diphenyl ethers and strategies for acceleration: A review. International Biodeterioration & Biodegradation, 129: 23–32
CrossRef ADS Google scholar
[76]
Zhuang Y, Ahn S, Luthy R G (2010). Debromination of polybrominated diphenyl ethers by nanoscale zerovalent iron: pathways, kinetics, and reactivity. Environmental Science & Technology, 44(21): 8236–8242
CrossRef ADS Google scholar
[77]
Zhuang Y, Ahn S, Seyfferth A L, Masue-Slowey Y, Fendorf S, Luthy R G (2011). Dehalogenation of polybrominated diphenyl ethers and polychlorinated biphenyl by bimetallic, impregnated, and nanoscale zerovalent iron. Environmental Science & Technology, 45(11): 4896–4903
CrossRef ADS Google scholar
[78]
Zhuang Y, Jin L, Luthy R G (2012). Kinetics and pathways for the debromination of polybrominated diphenyl ethers by bimetallic and nanoscale zerovalent iron: Effects of particle properties and catalyst. Chemosphere, 89(4): 426–432
CrossRef ADS Google scholar
[79]
Zumreoglukaran B (2006). The coordination chemistry of Vitamin C: An overview. Coordination Chemistry Reviews, 250(17–18): 2295–2307
CrossRef ADS Google scholar

Acknowledgements

The authors thank the Major Science and Technology Program for Water Pollution Control and Treatment, National Water Grant (No. 2017ZX07202002), the Key-Area Research and Development Program of Guangdong Provice (No. 2019B110205003), and the National Natural Science Foundation of China (Grant No. 51979141).

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