Citation: Chun-Ying Xu, Xiao-Lin Luan, Yuan-Yuan Cui, Cheng-Xiong Yang. One-pot in situ doping synthesis of phenylboronic acid-functionalized magnetic-cyclodextrin microporous organic network for specific enrichment and detection of sulfonylurea herbicides[J]. Chinese Chemical Letters, ;2025, 36(9): 110937. doi: 10.1016/j.cclet.2025.110937 shu

One-pot in situ doping synthesis of phenylboronic acid-functionalized magnetic-cyclodextrin microporous organic network for specific enrichment and detection of sulfonylurea herbicides

School of Pharmaceutical Sciences, Medical Science and Technology Innovation Center, Shandong First Medical University & Shandong Academy of Medical Sciences, Ji’nan 250117, China

Received Date: 8 July 2024
Revised Date: 13 October 2024
Accepted Date: 8 February 2025
Available Online: 8 February 2025

Figures(5)

Microporous organic networks (MONs) are attractive adsorbents for use in sample pretreatment owning to their unique structure and properties. However, methods for constructing functional MONs are still limited because the lack of monomers via direct synthesis and their complex procedures via post-modification. To address this issue, a facile one-pot in situ doping strategy was proposed herein for synthesis a novel phenylboronic acid-functionalized magnetic cyclodextrin-based microporous organic network ([PBA]_3/4−MCD-MON-0.04). [PBA]_3/4−MCD-MON-0.04 was used for the selective and efficient extraction of sulfonylurea herbicides (SUHs) from complex food and environmental water samples via the synergistic hydrogen bonding, host-guest, hydrophobic and π-π interactions and the specific B-N coordination. [PBA]_3/4−MCD-MON-0.04 had a large surface area, high saturation magnetism, good reusability, and remarkable stability. A rapid, sensitive, and selective method was proposed for monitoring SUHs from diverse matrices. This study provides a new strategy for synthesizing novel and multifunctional magnetic CD-MONs-based adsorbents and reveals the considerable potential of CD-MONs in sample pretreatment.
- Cyclodextrin microporous organic network,
- Magnetic solid phase extraction,
- In situ doping,
- Sulfonylurea herbicide,
- B-N coordination
1. [1]
  Y.R. Yamada, M. Murase, Y. Goto, et al., J. Agric. Food Chem. 71 (2023) 5006–5015. doi: 10.1021/acs.jafc.2c09077
2. [2]
  C.S. Li, N. Zhang, J.X. Chen, et al., Environ. Pollut. 255 (2019) 113150. doi: 10.1016/j.envpol.2019.113150
3. [3]
  Y. de Lafontaine, C. Beauvais, A.J. Cessn, et al., Sci. Total Environ. 479-480 (2014) 1–10. doi: 10.1016/j.scitotenv.2014.01.094
4. [4]
  M. Singh, A. Srivastava, Y.K. Sharma, S. Singh, S.P. Singh, Microchim. Acta 187 (2020) 490. doi: 10.1007/s00604-020-04464-8
5. [5]
  J.P. Ma, S. Li, G.G. Wu, et al., J. Colloid Interf. Sci. 553 (2019) 834–844. doi: 10.1016/j.jcis.2019.06.082
6. [6]
  X.L. Guo, T.Z. Ren, J.C. Ji, Y. Yang, X. Di, Food Chem. 396 (2022) 133652. doi: 10.1016/j.foodchem.2022.133652
7. [7]
  M.J. Lerma-Garcıá, E.F. Simó-Alfonso, M. Zougagh, Á. Ríos, Talanta 105 (2013) 372–378. doi: 10.1016/j.talanta.2012.10.056
8. [8]
  Y. Peng, Y. Xie, J. Luo, et al., Anal. Chim. Acta 674 (2010) 190–200. doi: 10.1016/j.aca.2010.06.022
9. [9]
  S.H. Zhang, X.F. Yin, Q. Yang, C. Wang, Z. Wang, Anal. Bioanal. Chem. 401 (2011) 1071–1081. doi: 10.1007/s00216-011-5138-5
10. [10]
  A. Gure, F.J. Lara, A.M. García-Campaña, N. Megersa, M. del Olmo-Iruela, Food Chem. 170 (2015) 348–353. doi: 10.1016/j.foodchem.2014.08.065
11. [11]
  K.J. Tang, X.H. Gu, Q.S. Luo, et al., Food Chem. 150 (2014) 106–112. doi: 10.1016/j.foodchem.2013.10.152
12. [12]
  J.Y. Wu, S.Y. Luo, X.J. Huang, Chem. Eng. J. 455 (2023) 140786. doi: 10.1016/j.cej.2022.140786
13. [13]
  J.H. Yang, C.X. Cui, L.B. Qu, et al., Microchem. J. 141 (2018) 369–376. doi: 10.1016/j.microc.2018.05.049
14. [14]
  J.P. Ma, L.H. Jiang, G.G. Wu, et al., J. Chromatogr. A 1466 (2016) 12–20. doi: 10.1016/j.chroma.2016.08.065
15. [15]
  H. Qi, L.Y. Jiang, Q. Jia, Chin. Chem. Lett. 32 (2021) 2629–2636. doi: 10.1016/j.cclet.2021.01.037
16. [16]
  C. Tian, Z.K. Wu, M. He, B.B. Chen, B. Hu, J. Sep. Sci. 45 (2022) 1746–1756. doi: 10.1002/jssc.202200055
17. [17]
  Z.Y. He, D.H. Liu, R.H. Li, Z.Q. Zhou, P. Wang, Anal. Chim. Acta 747 (2012) 29–35. doi: 10.1016/j.aca.2012.08.015
18. [18]
  S.S. Miao, M.S. Wu, H.G. Zuo, et al., J. Agric. Food Chem. 63 (2015) 3634–3645. doi: 10.1021/jf506239b
19. [19]
  Y.F. Zhou, M.X. Zhao, Z. Meng, et al., Microchim. Acta 186 (2019) 486. doi: 10.1007/s00604-019-3536-0
20. [20]
  M. Bouri, M. Gurau, R. Salghi, et al., Anal. Bioanal. Chem. 404 (2012) 1529–1538. doi: 10.1007/s00216-012-6221-2
21. [21]
  Y. Qi, M.F. Wan, A.M. Abd El-Aty, et al., Microchim. Acta 187 (2020) 279. doi: 10.1007/s00604-020-04243-5
22. [22]
  D.D. Wang, Y. Zhao, M.N. Ou Yang, H.M. Guo, Z.H. Yang, J. Chromatogr. A 1601 (2019) 53–59. doi: 10.1016/j.chroma.2019.05.011
23. [23]
  Y.Y. Cui, X.Q. He, C.X. Yang, X.P. Yan, Trends Anal. Chem. 139 (2021) 116268. doi: 10.1016/j.trac.2021.116268
24. [24]
  S.H. Li, L.L. Bian, C.Y. Yang, A.V. Schepdael, X. Wang, J. Hazard. Mater. 438 (2022) 129505. doi: 10.1016/j.jhazmat.2022.129505
25. [25]
  L. Liu, H.C. Tu, F. Liu, et al., Chem. Eng. J. 442 (2022) 136171. doi: 10.1016/j.cej.2022.136171
26. [26]
  X.H. Li, Y.Y. Cui, X. Wu, A. Abdukayum, C.X. Yang, Food Chem. 429 (2023) 136808. doi: 10.1016/j.foodchem.2023.136808
27. [27]
  X.Q. He, Y.Y. Cui, C.X. Yang, ACS Appl. Mater. Interfaces 13 (2021) 39905–39914. doi: 10.1021/acsami.1c11148
28. [28]
  X.H. Li, Y.Y. Cui, S.L. Ji, A. Abdukayum, C.X. Yang, Food Chem. 443 (2024) 138559. doi: 10.1016/j.foodchem.2024.138559
29. [29]
  C.Y. Li, J.M. Liu, Z.H. Wang, et al., J. Hazard. Mater. 384 (2020) 121348. doi: 10.1016/j.jhazmat.2019.121348
30. [30]
  Y.Y. Cui, Y.P. Bi, C.X. Yang, Chem. Eng. J. 435 (2022) 134829. doi: 10.1016/j.cej.2022.134829
31. [31]
  C.Y. Xu, C.Q. Zhen, Y.J. He, Y.Y. Cui, C.X. Yang, J. Chromatogr. A 1728 (2024) 464991. doi: 10.1016/j.chroma.2024.464991
32. [32]
  L. Yu, J. Ding, Y.L. Wang, P. Liu, Y.Q. Feng, Anal. Chem. 88 (2016) 1286–1293. doi: 10.1021/acs.analchem.5b03720
33. [33]
  Z.Y. Li, B. Luo, L.Z. Yu, F. Lan, Y. Wu, J. Mater. Chem. B 9 (2021) 453. doi: 10.1039/d0tb01901a
34. [34]
  J.S. Chen, X.W. Min, P. Li, et al., Anal. Chim. Acta 879 (2015) 41–47. doi: 10.1016/j.aca.2015.03.058
35. [35]
  S.S. Chi, C. Peng, Y.H. Lan, et al., J. Chromatogr. A 1590 (2019) 10–18. doi: 10.1016/j.chroma.2018.12.067
36. [36]
  Y. Zhang, M. Mei, X.J. Huang, D.X. Yuan, Anal. Chim. Acta 899 (2015) 75–84. doi: 10.1159/000374054
37. [37]
  M. Pei, X.Y. Zhu, X.J. Huang, J. Chromatogr. A 1531 (2018) 13–21. doi: 10.1016/j.chroma.2017.11.030
38. [38]
  Z.X. Cai, X. Zhou, Y.S. Yang, et al., Chem. Eng. J. 466 (2023) 143315. doi: 10.1016/j.cej.2023.143315
39. [39]
  S.C. Jiang, Z. Li, X.M. Yang, et al., Food Chem. 404 (2023) 134652. doi: 10.1016/j.foodchem.2022.134652
40. [40]
  M.M. Xu, J.M. Wang, L.H. Zhang, et al., J. Hazard. Mater. 429 (2022) 128288. doi: 10.1016/j.jhazmat.2022.128288
41. [41]
  Z.X. Cai, Z. Li, Q.Q. Wang, et al., J. Hazard. Mater. 462 (2024) 132746. doi: 10.1016/j.jhazmat.2023.132746
1. [1]
  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
2. [2]
  Ning Zhang , Mengjie Qin , Jiawen Zhu , Xuejing Lou , Xiao Tian , Wende Ma , Youmei Wang , Minghua Lu , Zongwei Cai . Thickness-controllable synthesis of metal-organic framework based hollow nanoflowers with magnetic core via liquid phase epitaxy for phosphopeptides enrichment. Chinese Chemical Letters, 2025, 36(4): 110177-. doi: 10.1016/j.cclet.2024.110177
3. [3]
  Xiaxia LIU , Xiaofang MA , Luxia GUO , Xianda HAN , Sisi FENG . Structure and magnetic properties of Mn(Ⅱ) coordination polymers regulated by N-auxiliary ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 587-596. doi: 10.11862/CJIC.20240269
4. [4]
  Bin Feng , Tao Long , Ruotong Li , Yuan-Li Ding . Rationally constructing metallic Sn-ZnO heterostructure via in-situ Mn doping for high-rate Na-ion batteries. Chinese Chemical Letters, 2025, 36(2): 110273-. doi: 10.1016/j.cclet.2024.110273
5. [5]
  Le Ye , Wei-Xiong Zhang . Structural phase transition in a new organic-inorganic hybrid post-perovskite: (N,N-dimethylpyrrolidinium)[Mn(N(CN)2)3]. Chinese Journal of Structural Chemistry, 2024, 43(6): 100257-100257. doi: 10.1016/j.cjsc.2024.100257
6. [6]
  Yuxiang Zhang , Jia Zhao , Sen Lin . Nitrogen doping retrofits the coordination environment of copper single-atom catalysts for deep CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100415-100415. doi: 10.1016/j.cjsc.2024.100415
7. [7]
  Jaeyong Ahn , Zhenping Li , Zhiwei Wang , Ke Gao , Huagui Zhuo , Wanuk Choi , Gang Chang , Xiaobo Shang , Joon Hak Oh . Surface doping effect on the optoelectronic performance of 2D organic crystals based on cyano-substituted perylene diimides. Chinese Chemical Letters, 2024, 35(9): 109777-. doi: 10.1016/j.cclet.2024.109777
8. [8]
  Peng Jia , Yunna Guo , Dongliang Chen , Xuedong Zhang , Jingming Yao , Jianguo Lu , Liqiang Zhang . In-situ imaging electrocatalysis in a solid-state Li-O₂ battery with CuSe nanosheets as air cathode. Chinese Chemical Letters, 2024, 35(5): 108624-. doi: 10.1016/j.cclet.2023.108624
9. [9]
  Han Yan , Jingming Yao , Zhangran Ye , Qiaoquan Lin , Ziqi Zhang , Shulin Li , Dawei Song , Zhenyu Wang , Chuang Yu , Long Zhang . Al-F co-doping towards enhanced electrolyte-electrodes interface properties for halide and sulfide solid electrolytes. Chinese Chemical Letters, 2025, 36(1): 109568-. doi: 10.1016/j.cclet.2024.109568
10. [10]
  Zhaodong WANG . In situ synthesis, crystal structure, and magnetic characterization of a trinuclear copper complex based on a multi-substituted imidazo[1,5-a]pyrazine scaffold. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 597-604. doi: 10.11862/CJIC.20240268
11. [11]
  Xiangdong Lai , Tengfei Liu , Zengchao Guo , Yihan Wang , Jiang Xiao , Qingxiu Xia , Xiaohui Liu , Hui Jiang , Xuemei Wang . In situ formed fluorescent gold nanoclusters inhibit hair follicle regeneration in oxidative stress microenvironment via suppressing NFκB signal pathway. Chinese Chemical Letters, 2025, 36(2): 109762-. doi: 10.1016/j.cclet.2024.109762
12. [12]
  Wenhao Feng , Chunli Liu , Zheng Liu , Huan Pang . In-situ growth of N-doped graphene-like carbon/MOF nanocomposites for high-performance supercapacitor. Chinese Chemical Letters, 2024, 35(12): 109552-. doi: 10.1016/j.cclet.2024.109552
13. [13]
  Xiaoxiao Huang , Zhi-Long He , Yangpeng Chen , Lei Li , Zhenyu Yang , Chunyang Zhai , Mingshan Zhu . Novel P-doping-tuned Pd nanoflowers/S,N-GQDs photo-electrocatalyst for high-efficient ethylene glycol oxidation. Chinese Chemical Letters, 2024, 35(6): 109271-. doi: 10.1016/j.cclet.2023.109271
14. [14]
  Yan-Ran Weng , Wen-Fu Tian , Wen-Jing Ding , Bi-He Ren , De-Hou Liu , Jia-Ying Tang , Feng Zhou , Xiao-Gang Chen , Xian-Jiang Song , Hui-Peng Lv , Yong Ai . Homochiral organic ferroelastics with plastic phase transition. Chinese Chemical Letters, 2025, 36(7): 110188-. doi: 10.1016/j.cclet.2024.110188
15. [15]
  Haoting Wang , Mengfan Luo , Yuzhong Wang , Jialong Yin , Heng Zhang , Jia Zhao , Bo Lai . Mn(Ⅱ) enhanced permanganate oxidation of trace organic pollutants in water: Critical role of in situ formation of colloidal MnO₂. Chinese Chemical Letters, 2025, 36(6): 110348-. doi: 10.1016/j.cclet.2024.110348
16. [16]
  Pingping Wang , Huixian Miao , Kechuan Sheng , Bin Wang , Fan Feng , Xuankun Cai , Wei Huang , Dayu Wu . Efficient blue-light-excitable copper(Ⅰ) coordination network phosphors for high-performance white LEDs. Chinese Chemical Letters, 2024, 35(4): 108600-. doi: 10.1016/j.cclet.2023.108600
17. [17]
  Cheng Cheng , Nasir Ali , Ji Liu , Juan Qiao , Ming Wang , Li Qi . Construction of degradable liposome-templated microporous metal-organic frameworks with commodious space for enzymes. Chinese Chemical Letters, 2024, 35(11): 109812-. doi: 10.1016/j.cclet.2024.109812
18. [18]
  Hao Sun , Xiaoxue Li , Baoyu Wu , Kai Zhu , Yinyi Gao , Tianzeng Bao , Hongbin Wu , Dianxue Cao . Direct regeneration of spent LiFePO₄ cathode material via a simple solid-phase method. Chinese Chemical Letters, 2025, 36(6): 110041-. doi: 10.1016/j.cclet.2024.110041
19. [19]
  Jialin Cai , Yizhe Chen , Ruiwen Zhang , Cheng Yuan , Zeyu Jin , Yongting Chen , Shiming Zhang , Jiujun Zhang . Interfacial Pt-N coordination for promoting oxygen reduction reaction. Chinese Chemical Letters, 2025, 36(2): 110255-. doi: 10.1016/j.cclet.2024.110255
20. [20]
  Dai-Huo Liu , Ao Wang , Hong-Yan Lü , Xing-Long Wu , Dan Luo , Wen-Hao Li , Jin-Zhi Guo , Haozhen Dou , Qianyi Ma , Zhongwei Chen . In situ constructing (MnS/Mn₂SnS₄)@N,S-ACTs heterostructure with superior Na/Li-storage capabilities in half-cells and pouch full-cells. Chinese Chemical Letters, 2024, 35(11): 109285-. doi: 10.1016/j.cclet.2023.109285

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(7)
HTML views(1)

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