Citation: Mengyuan Li, Xitong Ren, Yanmei Gao, Mengyao Mu, Shiping Zhu, Shufang Tian, Minghua Lu. Constructing bifunctional magnetic porous poly(divinylbenzene) polymer for high-efficient removal and sensitive detection of bisphenols[J]. Chinese Chemical Letters, ;2024, 35(12): 109699. doi: 10.1016/j.cclet.2024.109699 shu

Constructing bifunctional magnetic porous poly(divinylbenzene) polymer for high-efficient removal and sensitive detection of bisphenols

Mengyuan Li ^a ,
Xitong Ren ^b ,
Yanmei Gao ^a ,
Mengyao Mu ^a ,
Shiping Zhu ^a ,
Shufang Tian ^a ,
Minghua Lu ^{a, *,}

a.
College of Chemistry and Molecular Sciences, Henan University, Kaifeng 475004, China
b.
Key Laboratory for Special Functional Materials of Ministry of Education, School of Materials Science and Engineering, Henan University, Kaifeng 475004, China

mhlu@henu.edu.cn

Received Date: 11 December 2023
Revised Date: 14 February 2024
Accepted Date: 27 February 2024
Available Online: 1 March 2024

Figures(4)

In view of widespread existence and toxicity, removal and detection of bisphenols is imperative to assess environmental risks and reduce harm to human health. Although many techniques have been reported, constructing fast and sensitive method remains a challenge. Herein, porous poly(divinylbenzene) polymer was synthesized in-situ on the Fe₃O₄ particles by means of distillation-precipitation polymerization and functioned as sorbents to extract bisphenols. Employing Fe₃O₄@poly(divinylbenzene) as sorbent, a magnetic solid-phase extraction coupling with liquid chromatography was developed to detect trace bisphenols in water. This method presented low detection limits (0.01–0.03 ng/mL), high enrichment ability (enrichment factor, 327–343), and good reproducibility. Moreover, the method showed satisfactory recoveries in the detection of lake water (80.60%-116.2%) and egg sample (75.17%-120.0%). Impressively, Fe₃O₄@PDVB has excellent adsorption capacity, which can realize rapid kinetic adsorption of bisphenols with equilibrium time all less than 10 s. The maximum adsorption capacities reached 1074.8, 1049.7, 1299.1 and 1329.5 mg/g for bisphenol F, bisphenol A, bisphenol B and bisphenol AF with Langmuir isotherm model. The adsorption mechanism of Fe₃O₄@PDVB to bisphenols was investigated and demonstrated that hydrophobic interactions played a key role, together with assistance of stacking interactions and hydrogen interactions. Overall, this work provides a promising sorbent material with ultra-fast and large adsorption capacities for extraction of bisphenols from water.
- Sample pretreatment,
- Bisphenols (BPs),
- Porous organic polymer,
- Magnetic solid-phase extraction (MSPE),
- Adsorption
1. [1]
  Y. Ma, H. Liu, J. Wu, et al., Environ. Res. 176 (2019) 108575. doi: 10.1016/j.envres.2019.108575
2. [2]
  P. Qin, S. Zhu, M. Li, et al., Chin. Chem. Lett. 34 (2023) 108620. doi: 10.1016/j.cclet.2023.108620
3. [3]
  J. Liu, L. Zhang, G. Lu, et al., Environ. Saf. 208 (2021) 111481. doi: 10.1016/j.ecoenv.2020.111481
4. [4]
  A. Tarafdar, R. Sirohi, P.A. Balakumaran, et al., J. Hazard. Mater. 423 (2022) 127097. doi: 10.1016/j.jhazmat.2021.127097
5. [5]
  Z. Gao, S. Liu, L. Tan, et al., Sci. Total Environ. 836 (2022) 155628. doi: 10.1016/j.scitotenv.2022.155628
6. [6]
  F. Navarro-Lafuente, E. Adoamnei, J.J. Arense-Gonzalo, et al., Sci. Total Environ. 838 (2022) 156540. doi: 10.1016/j.scitotenv.2022.156540
7. [7]
  L. Han, X. Liu, X. Zhang, et al., J. Hazard. Mater. 424 (2022) 127559. doi: 10.1016/j.jhazmat.2021.127559
8. [8]
  B. Zhao, W. Xu, J. Ma, Q. Jia, Chin. Chem. Lett. 34 (2023) 107498. doi: 10.1016/j.cclet.2022.05.012
9. [9]
  Y. Gao, S. Zhu, M. Mu, et al., Chem. Eng. J. 475 (2023) 146459. doi: 10.1016/j.cej.2023.146459
10. [10]
  L. Qiao, C. Yu, R. Sun, J. Anal. Test. 6 (2022) 401–410. doi: 10.1007/s41664-021-00188-7
11. [11]
  A.K. EI-Deen, C.M. Hussain, Trends Environ. Anal. Chem. 39 (2023) e00211. doi: 10.1016/j.teac.2023.e00211
12. [12]
  X. Zhang, Y. Yang, P. Qin, al. et, Chin. Chem. Lett. 33 (2022) 903–906. doi: 10.1016/j.cclet.2021.07.003
13. [13]
  Z. Zhao, B. Liang, M. Wamg, et al., Chem. Eng. J. 427 (2022) 130943. doi: 10.1016/j.cej.2021.130943
14. [14]
  T. Lu, Q. Wang, J. Kong, al. et, Chem. Eng. J. 448 (2022) 137690. doi: 10.1016/j.cej.2022.137690
15. [15]
  J. Cheng, J. Ma, S. Li, et al., J. Hazard. Mater. 461 (2024) 132613. doi: 10.1016/j.jhazmat.2023.132613
16. [16]
  W. Ma, Q. Zheng, Y. He, et al., J. Am. Chem. Soc. 141 (2019) 18271–18277. doi: 10.1021/jacs.9b09189
17. [17]
  X. Yan, Y. Yang, G. Li, et al., Chin. Chem. Lett. 34 (2023) 107201. doi: 10.1016/j.cclet.2022.02.007
18. [18]
  L. Han, P. Qin, M. Li, et al., Chem. Eng. J. 456 (2023) 140969. doi: 10.1016/j.cej.2022.140969
19. [19]
  P. Qin, D. Chen, D. Li, et al., Food Chem. 409 (2023) 135272. doi: 10.1016/j.foodchem.2022.135272
20. [20]
  Y. Wu, H. Chen, Y. Chen, et al., Sci. China Chem. 65 (2022) 650–677. doi: 10.1007/s11426-021-1195-3
21. [21]
  X. Zhang, Y. Zhang, W. Zhou, et al., Chin. Chem. Lett. 34 (2023) 107368. doi: 10.1016/j.cclet.2022.03.091
22. [22]
  S. Qin, S. Qi, X. Li, et al., Sci. Total Environ. 728 (2020) 138789. doi: 10.1016/j.scitotenv.2020.138789
23. [23]
  B. Zhao, L. Jiang, Q. Jia, Chin. Chem. Lett. 33 (2022) 11–21. doi: 10.1016/j.cclet.2021.06.031
24. [24]
  L. Xiang, S. Yuan, F. Wang, et al., J. Am. Chem. Soc. 144 (2022) 15497–15508. doi: 10.1021/jacs.2c02881
25. [25]
  D. Chen, D. Luo, Y. He, et al., J. Am. Chem. Soc. 144 (2022) 16755–16760. doi: 10.1021/jacs.2c08327
26. [26]
  A. Alsbaiee, B.J. Smith, L. Xiao, et al., Nature 529 (2016) 190–U146. doi: 10.1038/nature16185
27. [27]
  X. Liu, C. Zhu, J. Yin, et al., Nat. Commun. 13 (2022) 2132. doi: 10.1038/s41467-022-29816-1
28. [28]
  R. Hu, M. Hassan, S. Zhang, W. Gong, Chin. Chem. Lett. 34 (2023) 107541. doi: 10.1016/j.cclet.2022.05.055
29. [29]
  Z. Li, Y. Yang, Adv. Mater. 34 (2022) 2107401. doi: 10.1002/adma.202107401
30. [30]
  H. Sai, K.W. Tan, K. Hur, Science 341 (2013) 530–534. doi: 10.1126/science.1238159
31. [31]
  Y. Zhu, P. Xu, X. Zhang, et al., Chem. Soc. Rev. 51 (2022) 1377–1414. doi: 10.1039/d1cs00871d
32. [32]
  S. Jiang, Z. Li, X. Yang, et al., Food Chem. 404 (2023) 134652. doi: 10.1016/j.foodchem.2022.134652
33. [33]
  M. Li, X. Ren, Y. Gao, et al., Chem. Commun. 58 (2022) 7574–7577. doi: 10.1039/d2cc02461f
34. [34]
  S.R. Churipard, K.S. Kanakikodi, D.A. Rambhia, et al., Chem. Eng. J. 380 (2020) 122481. doi: 10.1016/j.cej.2019.122481
35. [35]
  Y. Zhang, S. Wei, W. Zhang, et al., ChemSusChem 2 (2009) 867–872. doi: 10.1002/cssc.200900100
36. [36]
  J. Liu, Z. Sun, Y. Deng, et al., Angew. Chem. Int. Ed. 48 (2009) 5875–5879. doi: 10.1002/anie.200901566
37. [37]
  Y.S. Ho, G. McKay, Process Biochem. 34 (1999) 451–465. doi: 10.1016/S0032-9592(98)00112-5
38. [38]
  P. Wu, Z. Cai, H. Jin, et al., Sci. Total Environ. 650 (2019) 671–678. doi: 10.5194/isprs-archives-xlii-4-w16-671-2019
39. [39]
  A. Kubiak, M. Mackiewicz, M. Biesaga, et al., J. Environ. Chem. Eng. 9 (2021) 104947. doi: 10.1016/j.jece.2020.104947
40. [40]
  P. Lu, J. Cheng, Y. Li, et al., Carbohydr. Polym. 216 (2019) 149–156. doi: 10.1016/j.carbpol.2019.04.015
41. [41]
  Y. Feng, M. Sun, M. Sun, et al., J. Chromatogr. A 1673 (2022) 463132. doi: 10.1016/j.chroma.2022.463132
42. [42]
  L. Han, X. Zhang, D. Li, et al., Talanta 235 (2021) 122818. doi: 10.1016/j.talanta.2021.122818
43. [43]
  Y. Umezawa, S. Tsuboyama, H. Takahashi, et al., Carbohydr. Polym. 55 (1999) 10047–10056.
44. [44]
  T. Yamate, K. Kumazawa, H. Suzuki, et al., ACS Macro Lett. 5 (2016) 858–861. doi: 10.1021/acsmacrolett.6b00265
45. [45]
  D. Schneider, D. Mehlhorn, P. Zeigermann, et al., Chem. Soc. Rev. 45 (2016) 3439–3467. doi: 10.1039/C5CS00715A
1. [1]
  Congyan Liu , Xueyao Zhou , Fei Ye , Bin Jiang , Bo Liu . Confined electric field in nano-sized channels of ionic porous framework towards unique adsorption selectivity. Chinese Chemical Letters, 2025, 36(2): 109969-. doi: 10.1016/j.cclet.2024.109969
2. [2]
  Xiao-Hong Yi , Chong-Chen Wang . Metal-organic frameworks on 3D interconnected macroporous sponge foams for large-scale water decontamination: A mini review. Chinese Chemical Letters, 2024, 35(5): 109094-. doi: 10.1016/j.cclet.2023.109094
3. [3]
  Xudong Zhao , Yuxuan Wang , Xinxin Gao , Xinli Gao , Meihua Wang , Hongliang Huang , Baosheng Liu . Anchoring thiol-rich traps in 1D channel wall of metal-organic framework for efficient removal of mercury ions. Chinese Chemical Letters, 2025, 36(2): 109901-. doi: 10.1016/j.cclet.2024.109901
4. [4]
  Haodong Wang , Xiaoxu Lai , Chi Chen , Pei Shi , Houzhao Wan , Hao Wang , Xingguang Chen , Dan Sun . Novel 2D bifunctional layered rare-earth hydroxides@GO catalyst as a functional interlayer for improved liquid-solid conversion of polysulfides in lithium-sulfur batteries. Chinese Chemical Letters, 2024, 35(5): 108473-. doi: 10.1016/j.cclet.2023.108473
5. [5]
  Jiaxuan Wang , Tonghe Liu , Bingxiang Wang , Ziwei Li , Yuzhong Niu , Hou Chen , Ying Zhang . Synthesis of polyhydroxyl-capped PAMAM dendrimer/silica composites for the adsorption of aqueous Hg(II) and Ag(I). Chinese Chemical Letters, 2024, 35(12): 109900-. doi: 10.1016/j.cclet.2024.109900
6. [6]
  Fengxing Liang , Yongzheng Zhu , Nannan Wang , Meiping Zhu , Huibing He , Yanqiu Zhu , Peikang Shen , Jinliang Zhu . Recent advances in copper-based materials for robust lithium polysulfides adsorption and catalytic conversion. Chinese Chemical Letters, 2024, 35(11): 109461-. doi: 10.1016/j.cclet.2023.109461
7. [7]
  Zixuan Zhu , Xianjin Shi , Yongfang Rao , Yu Huang . Recent progress of MgO-based materials in CO₂ adsorption and conversion: Modification methods, reaction condition, and CO₂ hydrogenation. Chinese Chemical Letters, 2024, 35(5): 108954-. doi: 10.1016/j.cclet.2023.108954
8. [8]
  Yue Li , Minghao Fan , Conghui Wang , Yanxun Li , Xiang Yu , Jun Ding , Lei Yan , Lele Qiu , Yongcai Zhang , Longlu Wang . 3D layer-by-layer amorphous MoS_x assembled from [Mo₃S₁₃]^2- clusters for efficient removal of tetracycline: Synergy of adsorption and photo-assisted PMS activation. Chinese Chemical Letters, 2024, 35(9): 109764-. doi: 10.1016/j.cclet.2024.109764
9. [9]
  Chong Liu , Nanthi Bolan , Anushka Upamali Rajapaksha , Hailong Wang , Paramasivan Balasubramanian , Pengyan Zhang , Xuan Cuong Nguyen , Fayong Li . Critical review of biochar for the removal of emerging inorganic pollutants from wastewater. Chinese Chemical Letters, 2025, 36(2): 109960-. doi: 10.1016/j.cclet.2024.109960
10. [10]
  Linshan Peng , Qihang Peng , Tianxiang Jin , Zhirong Liu , Yong Qian . Highly efficient capture of thorium ion by citric acid-modified chitosan gels from aqueous solution. Chinese Chemical Letters, 2024, 35(5): 108891-. doi: 10.1016/j.cclet.2023.108891
11. [11]
  Dan Luo , Jinya Tian , Jianqiao Zhou , Xiaodong Chi . Anthracene-bridged "Texas-sized" box for the simultaneous detection and uptake of tryptophan. Chinese Chemical Letters, 2024, 35(9): 109444-. doi: 10.1016/j.cclet.2023.109444
12. [12]
  Hong-Rui Li , Xia Kang , Rui Gao , Miao-Miao Shi , Bo Bi , Ze-Yu Chen , Jun-Min Yan . Interfacial interactions of Cu/MnOOH enhance ammonia synthesis from electrochemical nitrate reduction. Chinese Chemical Letters, 2025, 36(2): 109958-. doi: 10.1016/j.cclet.2024.109958
13. [13]
  Shuangying Li , Qingxiang Zhou , Zhi Li , Menghua Liu , Yanhui Li . Sensitive measurement of silver ions in environmental water samples integrating magnetic ion-imprinted solid phase extraction and carbon dot fluorescent sensor. Chinese Chemical Letters, 2024, 35(5): 108693-. doi: 10.1016/j.cclet.2023.108693
14. [14]
  Muhammad Riaz , Rakesh Kumar Gupta , Di Sun , Mohammad Azam , Ping Cui . Selective adsorption of organic dyes and iodine by a two-dimensional cobalt(II) metal-organic framework. Chinese Journal of Structural Chemistry, 2024, 43(12): 100427-100427. doi: 10.1016/j.cjsc.2024.100427
15. [15]
  Hui Li , Yanxing Qi , Jia Chen , Juanjuan Wang , Min Yang , Hongdeng Qiu . Synthesis of amine-pillar[5]arene porous adsorbent for adsorption of CO₂ and selectivity over N₂ and CH₄. Chinese Chemical Letters, 2024, 35(11): 109659-. doi: 10.1016/j.cclet.2024.109659
16. [16]
  Ting Shi , Ziyang Song , Yaokang Lv , Dazhang Zhu , Ling Miao , Lihua Gan , Mingxian Liu . Hierarchical porous carbon guided by constructing organic-inorganic interpenetrating polymer networks to facilitate performance of zinc hybrid supercapacitors. Chinese Chemical Letters, 2025, 36(1): 109559-. doi: 10.1016/j.cclet.2024.109559
17. [17]
  Jing Wang , Pingping Li , Yuehui Wang , Yifan Xiu , Bingqian Zhang , Shuwen Wang , Hongtao Gao . Treatment and Discharge Evaluation of Phosphorus-Containing Wastewater. University Chemistry, 2024, 39(5): 52-62. doi: 10.3866/PKU.DXHX202309097
18. [18]
  Guang Huang , Lei Li , Dingyi Zhang , Xingze Wang , Yugai Huang , Wenhui Liang , Zhifen Guo , Wenmei Jiao . Cobalt’s Valor, Nickel’s Foe: A Comprehensive Chemical Experiment Utilizing a Cobalt-based Imidazolate Framework for Nickel Ion Removal. University Chemistry, 2024, 39(8): 174-183. doi: 10.3866/PKU.DXHX202311051
19. [19]
  Hui Wang , Abdelkader Labidi , Menghan Ren , Feroz Shaik , Chuanyi Wang . 微观结构调控的g-C₃N₄在光催化NO转化中的最新进展：吸附/活化位点的关键作用. Acta Physico-Chimica Sinica, 2025, 41(5): 100039-. doi: 10.1016/j.actphy.2024.100039
20. [20]
  Xinghong Cai , Qiang Yang , Yao Tong , Lanyin Liu , Wutang Zhang , Sam Zhang , Min Wang . AlO₂: A novel two-dimensional material with a high negative Poisson's ratio for the adsorption of volatile organic compounds. Chinese Chemical Letters, 2025, 36(2): 109586-. doi: 10.1016/j.cclet.2024.109586

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(329)
HTML views(12)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142