Citation: Yue Yong, Qian Zhiqi, Kong Fanan, Xiao Qin, Ren Shijie. Preparation and Adsorption Application Study of Fluorine-containing Conjugated Microporous Polymers[J]. Acta Chimica Sinica, ;2019, 77(6): 500-505. doi: 10.6023/A19020066 shu

Preparation and Adsorption Application Study of Fluorine-containing Conjugated Microporous Polymers

  • Corresponding author: Ren Shijie, rensj@scu.edu.cn
  • Received Date: 22 February 2019
    Available Online: 17 June 2019

    Fund Project: the National Natural Science Foundation of China 21404074the State Key Laboratory of Polymer Materials Engineering Sklpme2018-2-05the National Natural Science Foundation of China 21574087Project supported by the National Natural Science Foundation of China (Nos. 21574087, 21404074) and the State Key Laboratory of Polymer Materials Engineering (No. Sklpme2018-2-05)

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  • Water pollution arising from ever-growing domestic sewage and industrial organic pollutants has caused severe environmental and ecological problems in many parts of the world. It is urgent to seek appropriate ways to resolve oily wastewater and organic solvent pollution. Currently, physical adsorption is considered to be one of the most important methods to eliminate the oil contaminations in water thanks to its high efficiency and low cost. However, traditional adsorbent materials, such as activated carbon, zeolite and natural fibers, often suffer from low adsorption capacities, poor adsorption selectivity and recyclability. Thus, it is still of great importance to develop new absorbent materials for the separation and removal of oils or organic pollutants from water to address environmental issues. Conjugated microporous polymers (CMPs) are a class of organic porous polymers that have attracted extensive attention thanks to their large specific surface area, good physicochemical stability and unique extended π-conjugation along the polymer skeleton. Here we report a fluorine-containing conjugated microporous polymer (F-CMP), which was synthesized via Sonogashira cross-coupling reaction from 1, 3, 5-trifluoro-2, 4, 6-triiodobenzene and 1, 3, 5-triethynylbenzene. As a comparison, fluorine-free conjugated microporous polymer (H-CMP) was synthesized in the same condition from 1, 3, 5-tribromobenzene and 1, 3, 5-triethynybenzene. By introducing fluorine atom into the conjugated microporous skeleton, the contact angle of F-CMP with water reaches 145°, exhibiting excellent hydrophobicity. Nitrogen adsorption/desorption isotherms of the F-CMP show a high specific surface area of 638 m2·g-1, and the pore size distribution analysis shows the existence of both micropores and macropores. It can be obtained by adsorption experiments of oil and organic solvents that the adsorption capability of F-CMP increases significantly compared with its fluorine-free counterpart with similar structural skeleton. Due to high hydrophobicity and porous properties, F-CMP shows excellent adsorption properties towards to the removal of organic solvents and oils. The adsorption capability of F-CMP towards pump oil and chloroform can reach 40 g/g and 43 g/g, respectively. Meanwhile, F-CMP shows rapid adsorption rate and excellent adsorption recyclability. Thus, F-CMP displays promising application prospects in the field of organic pollutant adsorption and environmental remediation.
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    1. [1]

      Shannon, M. A.; Bohn, P. W.; Elimelech, M.; Georgiadis, J. G.; Marinas, B. J.; Mayes, A. M. Nature 2008, 452, 301.  doi: 10.1038/nature06599

    2. [2]

      Doshi, B.; Sillanpaa, M.; Kalliola, S. Water Res. 2018, 135, 262.  doi: 10.1016/j.watres.2018.02.034

    3. [3]

      Gupta, S.; Tai, N. H. J. Mater. Chem. A 2016, 4, 1550.  doi: 10.1039/C5TA08321D

    4. [4]

      Lei, E.; Li, W.; Ma, C.; Liu, S. Mater. Chem. Phys. 2018, 214, 291.  doi: 10.1016/j.matchemphys.2018.04.075

    5. [5]

      Mohan, D.; Singh, K. P.; Singh, V. K. J. Hazard Mater. 2008, 152, 1045.  doi: 10.1016/j.jhazmat.2007.07.079

    6. [6]

      Sakthivel, T.; Reid, D. L.; Goldstein, I.; Hench, L.; Seal, S. Environ. Sci. Technol. 2013, 47, 5843.  doi: 10.1021/es3048174

    7. [7]

      Likon, M.; Remskar, M.; Ducman, V.; Svegl, F. J. Environ. Manage. 2013, 114, 158.

    8. [8]

      Zhang, T.; Kong, L.; Dai, Y.; Yue, X.; Rong, J.; Qiu, F.; Pan, J. Chem. Eng. J. 2017, 309, 7.  doi: 10.1016/j.cej.2016.08.085

    9. [9]

      Chin, S. F.; Binti, R. A. N.; Pang, S. C. Mater. Lett. 2014, 115, 241.  doi: 10.1016/j.matlet.2013.10.061

    10. [10]

      Ong, C. C.; Sundera, M. S.; Mohamed, N. M.; Perumal, V.; Mohamed, S. M. S. ACS Omega. 2018, 3, 15907.  doi: 10.1021/acsomega.8b01566

    11. [11]

      Ji, C.; Zhang, K.; Li, L.; Chen, X.; Hu, J.; Yan, D.; Xiao, G.; He, X. J. Mater. Chem. A 2017, 5, 11263.  doi: 10.1039/C7TA02613G

    12. [12]

      Peng, D.; Jiang, W.; Li, F. F.; Zhang, L.; Liang, R. P.; Qiu, J. D. ACS Sustainable Chem. Eng. 2018, 6, 11685.  doi: 10.1021/acssuschemeng.8b01951

    13. [13]

      Dawson, R.; Laybourn, A.; Clowes, R.; Khimyak, Y. Z.; Adams, D. J.; Cooper, A. I. Macromolecules 2009, 42, 8809.  doi: 10.1021/ma901801s

    14. [14]

      Dawson, R.; Cooper, A. I.; Adams, D. J. Prog. Polym. Sci. 2012, 37, 530.  doi: 10.1016/j.progpolymsci.2011.09.002

    15. [15]

      Yan, T. T.; Xing, G. L.; Ben, T. Acta Chim. Sinica 2018, 76, 366.
       

    16. [16]

      Pang, C.; Luo, S. H.; Hao, Z. F.; Gao, J.; Huang, Z. H.; Yu, J. H.; Yu, S. M.; Wang, Z. Y. Chin. J. Org. Chem. 2018, 38, 2606.

    17. [17]

      Yu, S.; Xu, Y. J.; Jiang, J. X.; Ren, S. J. Acta Chim. Sinica 2015, 73, 629.
       

    18. [18]

      Xu, Y.; Jin, S.; Xu, H.; Nagai, A.; Jiang, D. Chem. Soc. Rev. 2013, 42, 8012.  doi: 10.1039/c3cs60160a

    19. [19]

      Jiang, J. X.; Su, F.; Trewin, A.; Wood, C. D.; Campbell, N. L.; Niu, H.; Dickinson, C.; Ganin, A. Y.; Rosseinsky, M. J.; Khimyak, Y. Z.; Cooper, A. I. Angew. Chem. Int. Ed. 2007, 46, 8574.  doi: 10.1002/anie.v46:45

    20. [20]

      Chen, Q.; Liu, D. P.; Luo, M.; Feng, L. J.; Zhao, Y. C.; Han, B. H. Small 2014, 10, 308.  doi: 10.1002/smll.v10.2

    21. [21]

      Wang, X.; Chen, B.; Dong, W.; Zhang, X.; Li, Z.; Xiang, Y.; Chen, H. Macromol. Rapid Commun. 2018, e1800494.

    22. [22]

      Kong, S. N.; Malik, A. U.; Qian, X. F.; Shu, M. H.; Xiao, W. D. Chin. J. Org. Chem. 2018, 38, 656.

    23. [23]

      Kong, S. N.; Qian, X. F.; Shu, M. H.; Xiao, W. D. Chin. J. Org. Chem. 2018, 38, 2754.

    24. [24]

      Xu, Y. J.; Wu, S. P.; Ren, S. J.; Ji, J.; Yue, Y.; Shen, J. J. RSC Adv. 2017, 7, 32496.  doi: 10.1039/C7RA05551J

    25. [25]

      He, Q.; Zhang, C.; Li, X.; Wang, X.; Mu, P.; Jiang, J. X. Acta Chim. Sinica 2018, 76, 202.
       

    26. [26]

      Liao, Y.; Cheng, Z.; Zuo, W.; Thomas, A.; Faul, C. F. J. ACS Appl. Mater. Interfaces 2017, 9, 38390.  doi: 10.1021/acsami.7b09553

    27. [27]

      Bildirir, H.; Osken, I.; Ozturk, T.; Thomas, A. Chemistry 2015, 21, 9306.  doi: 10.1002/chem.v21.26

    28. [28]

      Qiu, F.; Zhao, W.; Han, S.; Zhuang, X.; Lin, H.; Zhang, F. Polymers 2016, 8, 191.  doi: 10.3390/polym8050191

    29. [29]

      Yang, R. X.; Wang, T. T.; Deng, W. Q. Sci. Rep. 2015, 5, 10155.  doi: 10.1038/srep10155

    30. [30]

      Lee, J. S. M.; Wu, T. H.; Alston, B. M.; Briggs, M. E.; Hasell, T.; Hu, C. C.; Cooper, A. I. J. Mater. Chem. A 2016, 4, 7665.  doi: 10.1039/C6TA02319C

    31. [31]

      Qin, L.; Xu, G. j.; Yao, C.; Xu, Y. Polym. Chem. 2016, 7, 4599.  doi: 10.1039/C6PY00666C

    32. [32]

      Cha, M. C.; Lim, Y.; Choi, T. J.; Chang, J. Y. Macromol. Chem. Phys. 2017, 218, 1700219.  doi: 10.1002/macp.v218.20

    33. [33]

      Shen, X.; He, J.; Wang, K.; Li, X.; Wang, X.; Yang, Z.; Wang, N.; Zhang, Y.; Huang, C. ChemSusChem 2019, 12, 1342.  doi: 10.1002/cssc.v12.7

    34. [34]

      Zhao, X.; Wu, M.; Liu, Y.; Cao, S. Org. Lett. 2018, 20, 5564.  doi: 10.1021/acs.orglett.8b02228

    35. [35]

      Ju, Z.; Zhang, S.; Xing, Z.; Zhuang, Q.; Qiang, Y.; Qian, Y. ACS Appl. Mater. Interfaces 2016, 8, 20682.  doi: 10.1021/acsami.6b04763

    36. [36]

      Wang, X.; Mu, P.; Zhang, C.; Chen, Y.; Zeng, J.; Wang, F.; Jiang, J. X. ACS Appl. Mater. Interfaces 2017, 9, 20779.  doi: 10.1021/acsami.7b05345

    37. [37]

      Xu, L.; Xiao, G.; Chen, C.; Li, R.; Mai, Y.; Sun, G.; Yan, D. J. Mater. Chem. A 2015, 3, 7498.  doi: 10.1039/C5TA00383K

    38. [38]

      Wenk, H. H.; Sander, W. Eur. J. Org. Chem. 2002, 3927.

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