Photocatalytic degradation of tetracycline hydrochloride with visible light-responsive bismuth tungstate/conjugated microporous polymer

doi:10.1016/j.cjche.2021.08.030

中国化学工程学报 ›› 2022, Vol. 41 ›› Issue (1): 488-496.DOI: 10.1016/j.cjche.2021.08.030

• Resources and Environmental Technology • 上一篇下一篇

Photocatalytic degradation of tetracycline hydrochloride with visible light-responsive bismuth tungstate/conjugated microporous polymer

Fenghongkang Pan¹, Yimeng Wang^1,2, Kaiqing Zhao¹, Jun Hu¹, Honglai Liu¹, Ying Hu¹

1 State Key Laboratory of Chemical Engineering and School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China;
2 Prinbury Biopharm Co., Ltd, Shanghai 201203, China

收稿日期:2021-06-07 修回日期:2021-08-26 出版日期:2022-01-28 发布日期:2022-02-25
通讯作者: Jun Hu,E-mail address:junhu@ecust.edu.cn
基金资助:
This work is supported by the National Natural Science Foundation of China (91834301 and 21878076) and the Science and Technology Commission of Shanghai Municipality (19160712100).

Photocatalytic degradation of tetracycline hydrochloride with visible light-responsive bismuth tungstate/conjugated microporous polymer

Fenghongkang Pan¹, Yimeng Wang^1,2, Kaiqing Zhao¹, Jun Hu¹, Honglai Liu¹, Ying Hu¹

1 State Key Laboratory of Chemical Engineering and School of Chemistry & Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China;
2 Prinbury Biopharm Co., Ltd, Shanghai 201203, China

Received:2021-06-07 Revised:2021-08-26 Online:2022-01-28 Published:2022-02-25
Contact: Jun Hu,E-mail address:junhu@ecust.edu.cn
Supported by:
This work is supported by the National Natural Science Foundation of China (91834301 and 21878076) and the Science and Technology Commission of Shanghai Municipality (19160712100).

摘要/Abstract

摘要： Conjugated microporous polymer (CMP) is an emerging organic semiconductor with p-conjugated skeletons, and the bandgap of CMP can be flexibly modulated to harvest visible light. Based on the diversity and adjustability of monomers in CMP, we designed and synthesized donor-accepter (D-A) type BTNCMP through Sonogashira-Hagihara cross-coupling polymerization, further in-situ constructing series of inorganic/organic Z-scheme BW/BTN-n composite in the presence of Bi₂WO₆. After optimization, the tetracycline hydrochloride (C₀ = 10 mg·L^-1) degradation efficiency reached 84% with BW/BTN-2 as catalyst in 90 min under visible light irradiation, the apparent rate constant k₁ is 0.017 min^-1, which is 1.7 and 5.7 times higher than bare Bi₂WO₆ and BTN-CMP. X-ray photoelectron spectra and UV–Vis diffuse spectra showed that the enhanced photocatalytic activity originated from the tight heterojunction between Bi₂WO₆ and BTN-CMP, which can extend the light absorption range and facilitate the separation and transport of photogenerated charges in the interface of heterojunction. The active species trapping experiments and electron spin resonance technique revealed that h⁺ was the dominant active species during the photodegradation process of tetracycline hydrochloride (TCH). The present study demonstrated the feasibility to construct inorganic/organic composite for the photocatalytic degradation of environmental pollutants.

关键词: Photochemistry, Degradation, Visible light response, Pollution, Inorganic/organic heterojunction composite

Abstract: Conjugated microporous polymer (CMP) is an emerging organic semiconductor with p-conjugated skeletons, and the bandgap of CMP can be flexibly modulated to harvest visible light. Based on the diversity and adjustability of monomers in CMP, we designed and synthesized donor-accepter (D-A) type BTNCMP through Sonogashira-Hagihara cross-coupling polymerization, further in-situ constructing series of inorganic/organic Z-scheme BW/BTN-n composite in the presence of Bi₂WO₆. After optimization, the tetracycline hydrochloride (C₀ = 10 mg·L^-1) degradation efficiency reached 84% with BW/BTN-2 as catalyst in 90 min under visible light irradiation, the apparent rate constant k₁ is 0.017 min^-1, which is 1.7 and 5.7 times higher than bare Bi₂WO₆ and BTN-CMP. X-ray photoelectron spectra and UV–Vis diffuse spectra showed that the enhanced photocatalytic activity originated from the tight heterojunction between Bi₂WO₆ and BTN-CMP, which can extend the light absorption range and facilitate the separation and transport of photogenerated charges in the interface of heterojunction. The active species trapping experiments and electron spin resonance technique revealed that h⁺ was the dominant active species during the photodegradation process of tetracycline hydrochloride (TCH). The present study demonstrated the feasibility to construct inorganic/organic composite for the photocatalytic degradation of environmental pollutants.

Key words: Photochemistry, Degradation, Visible light response, Pollution, Inorganic/organic heterojunction composite

Fenghongkang Pan, Yimeng Wang, Kaiqing Zhao, Jun Hu, Honglai Liu, Ying Hu. Photocatalytic degradation of tetracycline hydrochloride with visible light-responsive bismuth tungstate/conjugated microporous polymer[J]. 中国化学工程学报, 2022, 41(1): 488-496.

参考文献

[1] M. Qiao, G.G. Ying, A.C. Singer, Y.G. Zhu, Review of antibiotic resistance in China and its environment, Environ. Int. 110(2018) 160–172.
[2] Q.Q. Zhang, G.G. Ying, C.G. Pan, Y.S. Liu, J.L. Zhao, Comprehensive evaluation of antibiotics emission and fate in the river basins of China: source analysis, multimedia modeling, and linkage to bacterial resistance, Environ. Sci. Technol. 49(11) (2015) 6772–6782.
[3] X.D. Zhu, Y.J. Wang, R.J. Sun, D.M. Zhou, Photocatalytic degradation of tetracycline in aqueous solution by nanosized TiO₂, Chemosphere 92(8) (2013) 925–932.
[4] Y.D. Liu, S.J. Zhou, F. Yang, H. Qin, Y. Kong, Degradation of phenol in industrial wastewater over the F-Fe/TiO₂ photocatalysts under visible light illumination, Chin. J. Chem. Eng. 24(12) (2016) 1712–1718.
[5] N. Daneshvar, D. Salari, A.R. Khataee, Photocatalytic degradation of azo dye acid red 14 in water on ZnO as an alternative catalyst to TiO₂, J. Photochem. Photobiol. A: Chem. 162(2–3) (2004) 317–322.
[6] A. Kambur, G.S. Pozan, I. Boz, Preparation, characterization and photocatalytic activity of TiO₂-ZrO₂ binary oxide nanoparticles, Appl. Catal. B: Environ. 115–116(2012) 149–158.
[7] G.C. Xi, B. Yue, J.Y. Cao, J.H. Ye, Fe₃O₄/WO₃ hierarchical core-shell structure: high-performance and recyclable visible-light photocatalysis, Chemistry 17(18) (2011) 5145–5154.
[8] M. Saeed, M. Muneer, N. Mumtaz, M. Siddique, N. Akram, M. Hamayun, AgCo₃O₄: Synthesis, characterization and evaluation of its photo-catalytic activity towards degradation of rhodamine B dye in aqueous medium, Chin. J. Chem. Eng. 26(6) (2018) 1264–1269.
[9] W. Zhu, F.Q. Sun, R. Goei, Y. Zhou, Facile fabrication of RGO-WO₃ composites for effective visible light photocatalytic degradation of sulfamethoxazole, Appl. Catal. B: Environ. 207(2017) 93–102.
[10] M. Ahmadi, H. Ramezani Motlagh, N. Jaafarzadeh, A. Mostoufi, R. Saeedi, G. Barzegar, S. Jorfi, Enhanced photocatalytic degradation of tetracycline and real pharmaceutical wastewater using MWCNT/TiO₂ nano-composite, J. Environ. Manag. 186(2017) 55–63.
[11] J.W. Fu, J.G. Yu, C.J. Jiang, B. Cheng, G-C₃N₄-based heterostructured photocatalysts, Adv. Energy Mater. 8(3) (2018) 1701503.
[12] X.C. Wang, K. Maeda, A. Thomas, K. Takanabe, G. Xin, J.M. Carlsson, K. Domen, M. Antonietti, A metal-free polymeric photocatalyst for hydrogen production from water under visible light, Nat. Mater. 8(1) (2009) 76–80.
[13] J.L. Zhang, Z. Ma, Porous g-C₃N₄ with enhanced adsorption and visible-light photocatalytic performance for removing aqueous dyes and tetracycline hydrochloride, Chin. J. Chem. Eng. 26(4) (2018) 753–760.
[14] F.M. Zhang, J.L. Sheng, Z.D. Yang, X.J. Sun, H.L. Tang, M. Lu, H. Dong, F.C. Shen, J. Liu, Y.Q. Lan, Rational design of MOF/COF hybrid materials for photocatalytic H₂ evolution in the presence of sacrificial electron donors, Angew. Chem. Int. Ed. Engl. 57(37) (2018) 12106–12110.
[15] F. Guo, S.Z. Yang, Y. Liu, P. Wang, J.E. Huang, W.Y. Sun, Size engineering of metal-organic framework MIL-101(Cr)-Ag hybrids for photocatalytic CO₂ reduction, ACS Catal. 9(9) (2019) 8464–8470.
[16] M. Wang, J.X. Liu, C.M. Guo, X.S. Gao, C.H. Gong, Y. Wang, B. Liu, X.X. Li, G.G. Gurzadyan, L.C. Sun, Metal–organic frameworks (ZIF-67) as efficient cocatalysts for photocatalytic reduction of CO₂: the role of the morphology effect, J. Mater. Chem. A 6(11) (2018) 4768–4775.
[17] B.C. Ma, S. Ghasimi, K. Landfester, F. Vilela, K.A.I. Zhang, Conjugated microporous polymer nanoparticles with enhanced dispersibility and water compatibility for photocatalytic applications, J. Mater. Chem. A 3(31) (2015) 16064–16071.
[18] Z.J. Wang, S. Ghasimi, K. Landfester, K.A. Zhang, Molecular structural design of conjugated microporous poly(benzooxadiazole) networks for enhanced photocatalytic activity with visible light, Adv. Mater. 27(40) (2015) 6265–6270.
[19] R.S. Sprick, J.-X. Jiang, B. Bonillo, S. Ren, T. Ratvijitvech, P. Guiglion, M.A. Zwijnenburg, D.J. Adams, A.I. Cooper, Tunable Organic Photocatalysts for Visible-Light-Driven Hydrogen Evolution, J. Am. Chem. Soc. 137(2015) 3265–3270.
[20] C.H. Dai, B. Liu, Conjugated polymers for visible-light-driven photocatalysis, Energy Environ. Sci. 13(1) (2020) 24–52.
[21] Y.L. Wong, J.M. Tobin, Z. Xu, F. Vilela, Conjugated porous polymers for photocatalytic applications, J. Mater. Chem. A 4(48) (2016) 18677–18686.
[22] Z.A. Lan, G.G. Zhang, X. Chen, Y.F. Zhang, K.A. Zhang, X.C. Wang, Reducing the exciton binding energy of donor-acceptor-based conjugated polymers to promote charge-induced reactions, Angew. Chem. Int. Ed. Engl. 58(30) (2019) 10236–10240.
[23] C. Yang, W. Huang, L.C. Da Silva, K.A.I. Zhang, X.C. Wang, Functional conjugated polymers for CO₂ reduction using visible light, Chem. Eur. J. 24(66) (2018) 17454–17458.
[24] K. Zhang, D. Kopetzki, P.H. Seeberger, M. Antonietti, F. Vilela, Surface area control and photocatalytic activity of conjugated microporous poly (benzothiadiazole) networks, Angew. Chem. Int. Ed. Engl. 52(5) (2013) 1432–1436.
[25] J. Yu, X.Q. Sun, X.X. Xu, C. Zhang, X.M. He, Donor-acceptor type triazine-based conjugated porous polymer for visible-light-driven photocatalytic hydrogen evolution, Appl. Catal. B: Environ. 257(2019) 117935.
[26] H.J. Hou, X.H. Zhang, D.K. Huang, X. Ding, S.Y. Wang, X.L. Yang, S.Q. Li, Y.G. Xiang, H. Chen, Conjugated microporous poly(benzothiadiazole)/TiO₂ heterojunction for visible-light-driven H₂ production and pollutant removal, Appl. Catal. B: Environ. 203(2017) 563–571.
[27] R. He, D.F. Xu, B. Cheng, J.G. Yu, W. Ho, Review on nanoscale Bi-based photocatalysts, Nanoscale Horiz. 3(5) (2018) 464–504.
[28] H. Fu, C. Pan, W. Yao, Y. Zhu, Visible-light-induced degradation of rhodamine B by nanosized Bi₂WO₆, J. Phys. Chem. B 109(47) (2005) 22432–22439.
[29] J.J. Wang, L. Tang, G.M. Zeng, Y.C. Deng, H.R. Dong, Y.N. Liu, L.L. Wang, B. Peng, C. Zhang, F. Chen, 0D/2D interface engineering of carbon quantum dots modified Bi₂WO₆ ultrathin nanosheets with enhanced photoactivity for full spectrum light utilization and mechanism insight, Appl. Catal. B: Environ. 222(2018) 115–123.
[30] S.H. Gu, L.Z. Wang, J.L. Zhang, Enhanced visible light photocatalytic activity of flower-like Bi₂WO₆Loaded with MnO_x, Chin. J. Chem. 35(2) (2017) 153–158.
[31] J.X. Jiang, A. Trewin, F.B. Su, C.D. Wood, H.J. Niu, J.T.A. Jones, Y.Z. Khimyak, A.I. Cooper, Microporous Poly(tri(4-ethynylphenyl)amine) networks: synthesis, properties, and atomistic simulation, Macromolecules 42(7) (2009) 2658–2666.
[32] J. Di, J.X. Xia, Y.P. Ge, H.P. Li, H.Y. Ji, H. Xu, Q. Zhang, H.M. Li, M.N. Li, Novel visible-light-driven CQDs/Bi₂WO₆ hybrid materials with enhanced photocatalytic activity toward organic pollutants degradation and mechanism insight, Appl. Catal. B: Environ. 168–169(2015) 51–61.
[33] F.T. Yu, Z.Q. Wang, S.C. Zhang, H.N. Ye, K.Y. Kong, X.Q. Gong, J.L. Hua, H. Tian, Molecular engineering of donor-acceptor conjugated polymer/g-C₃N₄ heterostructures for significantly enhanced hydrogen evolution under visible-light irradiation, Adv. Funct. Mater. 28(47) (2018) 1804512.
[34] S.Q. Zhang, T. Lv, Y. Mu, J.Q. Zheng, C.G. Meng, High adsorption of Cd (II) by modification of synthetic zeolites Y, A and mordenite with thiourea, Chin. J. Chem. Eng. 28(12) (2020) 3117–3125.
[35] D.B. Xu, L.L. Li, W.Q. Fan, F.G. Wang, H.Y. Bai, B.D. Mao, W.D. Shi, Preparation of WO₃ thin films by dip film-drawing for photoelectrochemical performance, Chin. J. Chem. Eng. 27(5) (2019) 1207–1211.
[36] Y.K. Huang, S.F. Kang, Y. Yang, H.F. Qin, Z.J. Ni, S.J. Yang, X. Li, Facile synthesis of Bi/Bi₂WO₆ nanocomposite with enhanced photocatalytic activity under visible light, Appl. Catal. B: Environ. 196(2016) 89–99.
[37] L.W. Shan, J.B. Mi, L.M. Dong, Z.D. Han, B. Liu, Enhanced photocatalytic properties of silver oxide loaded bismuth vanadate, Chin. J. Chem. Eng. 22(8) (2014) 909–913.
[38] Y.F. Liu, Y. Zou, H. Jiang, H.X. Gao, R.Z. Chen, Deactivation mechanism of betazeolite catalyst for synthesis of cumene by benzene alkylation with isopropanol, Chin. J. Chem. Eng. 25(9) (2017) 1195–1201.
[39] C.M. Li, G. Chen, J.X. Sun, J.C. Rao, Z.H. Han, Y.D. Hu, W.N. Xing, C.M. Zhang, Doping effect of phosphate in Bi₂WO₆ and universal improved photocatalytic activity for removing various pollutants in water, Appl. Catal. B: Environ. 188(2016) 39–47.
[40] D.J. Wang, G.L. Xue, Y.Z. Zhen, F. Fu, D.S. Li, Monodispersed Ag nanoparticles loaded on the surface of spherical Bi₂WO₆ nanoarchitectures with enhanced photocatalytic activities, J. Mater. Chem. 22(11) (2012) 4751.
[41] S.Y. Wang, X.L. Yang, H.J. Hou, X. Ding, S.H. Li, F. Deng, Y.G. Xiang, H. Chen, Highly efficient visible light induced photocatalytic activity of a novel in situ synthesized conjugated microporous poly(benzothiadiazole)–C₃N₄ composite, Catal. Sci. Technol. 7(2) (2017) 418–426.
[42] Z.J. Zhang, W.Z. Wang, L. Wang, S.M. Sun, Enhancement of visible-light photocatalysis by coupling with narrow-band-gap semiconductor: a case study on Bi₂S₃/Bi₂WO₆, ACS Appl. Mater. Interfaces 4(2) (2012) 593–597.
[43] R. Saffari, Z. Shariatinia, M. Jourshabani, Synthesis and photocatalytic degradation activities of phosphorus containing ZnO microparticles under visible light irradiation for water treatment applications, Environ. Pollut. 259(2020) 113902.
[44] S. Horikoshi, F. Hojo, H. Hidaka, N. Serpone, Environmental remediation by an integrated microwave/UV illumination technique. 8. fate of carboxylic acids, aldehydes, alkoxycarbonyl and phenolic substrates in a microwave radiation field in the presence of TiO₂Particles under UV irradiation, Environ. Sci. Technol. 38(7) (2004) 2198–2208.
[45] Z.Q. Ren, X.Y. Zhu, W. Liu, W. Sun, W.D. Zhang, J.T. Liu, Removal of aniline from wastewater using hollow fiber renewal liquid membrane, Chin. J. Chem. Eng. 22(11–12) (2014) 1187–1192.
[46] Y.Y. Wang, W.J. Jiang, W.J. Luo, X.J. Chen, Y.F. Zhu, Ultrathin nanosheets gC₃N₄@Bi₂WO₆ core-shell structure via low temperature reassembled strategy to promote photocatalytic activity, Appl. Catal. B: Environ. 237(2018) 633–640.
[47] J. Low, C.J. Jiang, B. Cheng, S. Wageh, A.A. Al-Ghamdi, J.G. Yu, A review of direct Z-scheme photocatalysts, Small Methods 1(5) (2017) 1700080.
[48] D.L. Huang, J. Li, G.M. Zeng, W.J. Xue, S. Chen, Z.H. Li, R. Deng, Y. Yang, M. Cheng, Facile construction of hierarchical flower-like Z-scheme AgBr/Bi₂WO₆ photocatalysts for effective removal of tetracycline: Degradation pathways and mechanism, Chem. Eng. J. 375(2019) 121991.

Photocatalytic degradation of tetracycline hydrochloride with visible light-responsive bismuth tungstate/conjugated microporous polymer

Photocatalytic degradation of tetracycline hydrochloride with visible light-responsive bismuth tungstate/conjugated microporous polymer

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