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Construction of Ionic Porous Organic Polymers (iPOPs) via Pyrylium Mediated Transformation

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Abstract

Two new ionic porous organic polymers (iPOPs) with different counter anions were successfully fabricated via well-known pyrylium mediated transformation into pyridinium. 13C solid-state NMR, XPS, and FTIR were analyzed and confirmed the formation of pyridinium in the network. Containing charged and aromatic networks, both iPOPs exhibit a high affinity towards toxic hexavalent chromium Cr(VI) ions. What is more, it has been demonstrated that both CO2 adsorption and Cr(VI) removal properties can be tuned by simply varying counter anions.

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References

  1. Li, H.; Li, J. H.; Thomas, A.; Liao, Y. Ultra-high surface area nitrogen-doped carbon aerogels derived from a Schiff-base porous organic polymer aerogel for CO2 storage and supercapacitors. Adv. Funct. Mater.2019, 29, 1904785.

    Article  Google Scholar 

  2. Shen, R.; Zhu, W.; Yan, X. G.; Li, T.; Liu, Y.; Li, Y. X.; Dai, S. Y.; Gu, Z. G. A porphyrin porous organic polymer with bicatalytic sites for highly efficient one-pot tandem catalysis. Chem. Commun.2019, 55, 822–825.

    Article  CAS  Google Scholar 

  3. Krishnan, S.; Suneesh, C. V. Fluorene-triazine conjugated porous organic polymer framework for superamplified sensing of nitroaromatic explosives. J. Photoch. Photobio. A2019, 371, 414–422.

    Article  CAS  Google Scholar 

  4. Weeraratne, K. S.; Alzharani, A. A.; El-Kaderi, H. M. Redox-active porous organic polymers as novel electrode materials for green rechargeable sodium-ion batteries. ACS Appl. Mater. Interfaces2019, 11, 23520–23526.

    Article  CAS  Google Scholar 

  5. Zhang, W. J.; Aguila, B.; Ma, S. Q. Potential applications of functional porous organic polymer materials. J. Mater. Chem. A2017, 5, 8795–8824.

    Article  CAS  Google Scholar 

  6. Gu, C.; Huang, N.; Chen, Y. C.; Qin, L. Q.; Xu, H.; Zhang, S. T.; Li, F. H.; Ma, Y. G.; Jiang, D. L. π-Conjugated microporous polymer films: designed synthesis, conducting properties, and photoenergy conversions. Angew. Chem. Int. Ed.2015, 54, 13594–13598.

    Article  CAS  Google Scholar 

  7. Li, Z. P.; Li, H.; Xia, H.; Mu, Y. Triarylboron-linked conjugated microporous polymers: sensing and removal of fluoride ions. Chem. Eur. J.2015, 21, 17355–17362.

    Article  CAS  Google Scholar 

  8. Buyukcakir, O.; Je, S. H.; Talapaneni, S. N.; Kim, D.; Coskun, A. Charged covalent triazine frameworks for CO2 capture and conversion. ACS Appl. Mater. Interfaces2017, 9, 7209–7216.

    Article  CAS  Google Scholar 

  9. Chen, G.; Huang, X.; Zhang, Y.; Sun, M.; Shen, J.; Huang, R.; Tong, M.; Long, Z.; Wang, X. Constructing POSS and viologen-linked porous cationic frameworks induced by the Zincke reaction for efficient CO2 capture and conversion. Chem. Commun.2018, 54, 12174–12177.

    Article  CAS  Google Scholar 

  10. Gang, X.; Bin, W. B.; Xin, Y. L.; Yi, R. B.; Ke, H. Y.; Fu, D.; Ileana, D.; Valerian, D.; Guang, S. Y. Hypervalent silicon-based, anionic porous organic polymers with solid microsphere or hollow nanotube morphologies and exceptional capacity for selective adsorption of cationic dyes. J. Mater. Chem. A2019, 3, 393–404.

    Google Scholar 

  11. Das, G.; Skorjanc, T.; Sharma, S. K.; Gandara, F.; Lusi, M.; Shankar Rao, D. S.; Vimala, S.; Krishna Prasad, S.; Raya, J.; Han, D. S.; Jagannathan, R.; Olsen, J. C.; Trabolsi, A. Violgenn-aasdd conjugated covalent organic networks via Zincke reaction. J. Am. Chem. Soc.2017, 139, 9558–9565.

    Article  CAS  Google Scholar 

  12. Shen, X. C.; Ma, S.; Xia, H.; Shi, Z.; Mua, Y.; Liu, X. M. Cattonic porous organic polymers as an excellent platform for highly efficient removal of pollutants from water. J. Mater. Chem. A2018, 6, 20653–20658.

    Article  CAS  Google Scholar 

  13. Liu, T. T.; Liang, J.; Huang, Y. B.; Cao, R. A bifunctional cationic porous organic polymer based on a Salen-(Al) metalloligand for the cycloaddition of carbon dioxide to produce cyclic carbonates. Chem. Commun.2016, 52, 13288–13291.

    Article  CAS  Google Scholar 

  14. Dong, D.; Zhang, H.; Zhou, B.; Sun, Y. F.; Zhang, H. L.; Cao, M.; Li, J. B.; Zhou, H.; Qian, H.; Lin, Z. Y.; Chen, H. G. Porous covalent organic frameworks for high transference number polymer-based electrolytes. Chem. Commun.2019, 55, 1458–1461.

    Article  CAS  Google Scholar 

  15. Huang, N.; Wang, P.; Addicoat, M. A.; Heine, T.; Jiang, D. Ionic covalent organic frameworks: design of a charged interface aligned on 1D channel walls and its unusual electrostatic functions. Angew. Chem. Int. Ed.2017, 56, 4982–4986.

    Article  CAS  Google Scholar 

  16. Zhao, Y. S.; Li, S. Q.; Zheng, X. S.; Tang, J. B.; She, Z. J.; Gao, G.; You, J. S. Rh/Cu-catalyzed cascade[4+2] vinylic C-H o-annulation and ring contraction of a-aryle enones with alkynes in air. Anqewi. Chem. Int. Ed.2017, 56, 4286–4289.

    Article  CAS  Google Scholar 

  17. Garciá-Acosta, B.; Comes, M.; Bricks, J. L.; Kudinova, M. A.; Kurdyukov, V. V.; Tolmachev, A. I. Sensory hybrid host materials for the selective chromo-fluorogenic detection of biogenic amines. Chem. Commun.2006, 21, 2239–2241.

    Article  Google Scholar 

  18. Martinez-Hayaa, R.; Bareckaa, M. H.; Miroa, P.; Marina, M. L.; Miranda, M. A. Photocatalytic treatment of cork wastewater pollutants. Degradation of gallic acid and trichloroanisole using triphenyl(thia)pyrylium salts. Appl. Catal. B2015, 179, 433–438.

    Article  Google Scholar 

  19. Katritzky, A. R.; Marson, C. M. Pyrylium mediated transformations of primary amino groups into other functional groups. Angew. Chem. Int. Ed.1984, 23, 420–429.

    Article  Google Scholar 

  20. Katritzky, L. R.; Manzo, R. H.; Lloyd, J. M.; Patel, R. C. Mechanism of the pyrylium/pyridinium ring interconversion. Mild preparative conditions for conversion of amines into pyridinium ions. Angew. Chem. Int. Ed.1980, 92, 315–316.

    Article  CAS  Google Scholar 

  21. Wang, H.; Qian, X. M.; Wang, K.; Su, M.; Haoyang, W. W.; Jiang, X.; Brzozowski, R.; Wang, M.; Gao, X.; Li, Y. M.; Xu, B. Q.; Eswara, P.; Hao, X. Q.; Gong, W. T.; Hou, J. L.; Cai, J. F.; Li, X. P. Supramolecular Kandinsky circles with high antibacterial activity. Nat. Commun. 2018, 9, 1815–1824.

    Article  Google Scholar 

  22. Qian, X. M.; Gong, W. T.; Wang, F. R.; Lin, Y.; Ning, G. L. A pyrylium-based colorimetric and fluorimetric chemosensor for the selective detection of lysine in aqueous environment and real sample. Tetrahedron Lett.2015, 56, 2764–2767.

    Article  CAS  Google Scholar 

  23. Gong, W. T.; Zhang, Q. L.; Wang, F. R.; Gao, B.; Lin, Y.; Ning, G. L. Selective sensing of H2PO4− (Pi) driven by the assembly of anthryl pyridinium ligands. Org. Biomol. Chem.2012, 10, 7578–7583.

    Article  CAS  Google Scholar 

  24. Qian, X. M.; Gong, W. T.; Li, X. P. Fluorescent cross-linked supramolecular polymer constructed by orthogonal self-assembly of metal-ligand coordination and host-guest interaction. Chem. Eur J.2016, 22, 6881–6890.

    Article  CAS  Google Scholar 

  25. Qian, X. M.; Gong, W. T.; Dhinakaran, M. K. Two bent-shaped π-organogelators: synthesis, fluorescence, self-assembly and detection of volatile acid vapours in gel films and in gel-gel states. Soft Matter2015, 11, 9179–9187.

    Article  CAS  Google Scholar 

  26. Gong, W. T.; Qian, X. M.; Wang, F. R. Synthesis and photophysical properties of new highly conjugated bispyrylium compounds. Heteroatom Chem.2013, 24, 66–71.

    Article  CAS  Google Scholar 

  27. Harris, F. W.; Chuang, K. C.; Huang, S. X.; Janimak, J. J.; Cheng, S. Z. D. Aromatic poly(pyridinium salt)s: synthesis and structure of organo-soluble, rigid-rod poly(pyridinium tetrafluoroborate)s. Polymer1994, 35, 4940–4948.

    Article  CAS  Google Scholar 

  28. Bhowmik, P. K.; Burchett, R. A.; Han, H.; Cebe, J. J. Synthesis and characterization of poly(pyridinium salt)s with organic counterion exhibiting both lyotropic liquid-crystalline and light-emitting properties. Macromolecules2001, 34, 7579–7581.

    Article  CAS  Google Scholar 

  29. Gomes, R.; Bhanja, P.; Bhaumik, A. A triazine-based covalent organic polymer for efficient CO2 adsorption. Chem. Commun. 2015, 51, 10050–10053.

    Article  CAS  Google Scholar 

  30. Che, S. Y.; Yang, Z. Z.; Popovs, I.; Luo, H. M.; Luo, Y. L.; Guo, W.; Chen, H.; Wang, T.; Jie, K. C.; Wang, C. M.; Dai, S. A succinct strategy for construction of nanoporous ionic organic networks from a pyrylium intermediate. Chem. Commun.0019, 55, 13450–13453.

    Article  Google Scholar 

  31. Pietrzak, R. XPS study and physico-chemical properties of nitrogen-enriched microporous activated carbon from high volatile bituminous coal. Fuel2009, 88, 1871–1877.

    Article  CAS  Google Scholar 

  32. Wang, Y.; Tao, J.; Xiong, S. H.; Lu, P.; Tang, J. T.; He, J. Q.; Javaid, M. U.; Pan, C. Y.; Yu, G. P. Ferrocene-based porous organic polymers for high-affinity iodine capture. Chem. Eng. J.2020, 380, 122420–122425.

    Article  CAS  Google Scholar 

  33. Li, X. M.; Zhou, M. J.; Jia, J. X.; Jia, Q. A water-insoluble viologen-based β-cyclodextrin polymer for selective adsorption toward anionic dyes. React. Funct. Polym.2018, 126, 20–26.

    Article  CAS  Google Scholar 

  34. Su, Y. Q.; Wang, Y. X.; Li, X. J.; Li, X. X.; Wang, R. H. Imidazolium-based porous organic polymers: anion exchange driven capture and luminescent probe of Cr2O72−. ACS Appl. Mater. Interfaces2016, 8, 18904–18911.

    Article  CAS  Google Scholar 

  35. Wen, T.; Fan, Q. H.; Tan, X. L.; Chen, Y. T.; Chen, C. L.; Xu, A. W.; Wang, X. K. A core-shell structure of polyaniline coated protonic titanate nanobelt composites for both Cr(VI) and humic acid removal. Polym. Chem.2016, 7, 785–794.

    Article  CAS  Google Scholar 

  36. Zhang, C. H.; Liu, Y. C.; Sun, L. B.; Shi, H. Z.; Shi, C.; Liang, Z. Q.; Li, J. Y. A zwitterionic ligand-based cationic metal-organic famework for rapidly selective dye capture and highly efficient Cr2O72− removal. Chem. Eur J.2018, 24, 2718–2724.

    Article  CAS  Google Scholar 

  37. Guo, D. M.; Ana, Q. D.; Xiao, Z. Y.; Zhai, S. R. Efficient removal of Pb(II), Cr(VI) and organic dyes by polydopamine modified chitosan aerogels. Carbohyd Polym.2018, 202, 306–314.

    Article  CAS  Google Scholar 

  38. Liang, X. T.; Fan, X. Y.; Li, R. M.; Li, S. R.; Shen, S. K.; Hu, D. D. Efficient removal of Cr(VI) from water by quaternized chitin/branched polyethylenimine biosorbent with hierarchical pore structure. Bioresource Technol.2018, 250, 178–184.

    Article  CAS  Google Scholar 

  39. Song, L.; Liu, F. Q.; Zhua, C. Q.; Li, A. M. Facile one-step fabrication of carboxymethyl cellulose based hydrogel for highly efficient removal of Cr(VI) under mild acidic condition. Chem. Eng. J.2019, 369, 641–651.

    Article  CAS  Google Scholar 

  40. Zhang, L.; Niu, W.; Sun, J.; Zhou, Q. Efficient removal of Cr(VI) from water by the uniform fiber ball loaded with polypyrrole: static adsorption, dynamic adsorption and mechanism studies. Chemosphere2020, 248, 126102–126112.

    Article  CAS  Google Scholar 

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Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (No. 21206016 for W.T. Gong, No. U1808210 for G.L. Ning), the Fundamental Research Funds for the Central Universities (No. DUT-17LK07), and the Natural Science Foundation of Liaoning province (No. 2019-MS-046).

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Authors and Affiliations

  1. State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian, 116024, China

    Shi-Yue Zhang, Wei-Tao Gong, Wei-Dong Qu, Xiao-Rong Deng, Kai-Xun Dong, Shu-Guang Zhang & Gui-Ling Ning

  2. Engineering Laboratory of Boric and Magnesic Functional Material Preparative and Applied Technology, Dalian, 116024, China

    Wei-Tao Gong & Gui-Ling Ning

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  1. Shi-Yue Zhang
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Correspondence to Wei-Tao Gong or Gui-Ling Ning.

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Zhang, SY., Gong, WT., Qu, WD. et al. Construction of Ionic Porous Organic Polymers (iPOPs) via Pyrylium Mediated Transformation. Chin J Polym Sci 38, 958–964 (2020). https://doi.org/10.1007/s10118-020-2436-4

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  • DOI: https://doi.org/10.1007/s10118-020-2436-4

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