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Massive Preparation of Coumarone-indene Resin-based Hyper-crosslinked Polymers for Gas Adsorption

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Abstract

Hyper-crosslinked polymers (HCPs) are promising materials for gas capture and storage because of their low cost and easy preparation. In this work, we report the massive preparation of coumarone-indene resin-based hyper-crosslinked polymers via one-step Friedel-Crafts alkylation. Low-cost coumarone-indene resin serves as the new building block and chloroform is employed as both solvent and external crosslinker. A maximum surface area of 966 m2·g−1 is achieved, which is comparable with that of previously-reported coal tar-based porous organic polymers. Most importantly, a large number of heteroatoms including inherent oxygen atoms and introduced chlorine atoms in obtianed HCPs further enhance the interaction between specific sorbate molecule and adsorbent. Therefore, optimal structural and chemical property endow the new coumarone-indene resin-based HCPs with decent gas storage capacity (14.60 wt% at 273 K and 0.1 MPa for CO2; 1.18 wt% at 77.3 K and 0.1 MPa for H2). These results demonstrate that new HCPs are potential candidates for applications in CO2 and H2 capture.

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References

  1. Xu, F.; Tang, Z.; Huang, S.; Chen, L.; Liang, Y.; Mai, W.; Zhong, H.; Fu, R.; Wu, D. Facile synthesis of ultrahigh-surface-area hollow carbon nanospheres for enhanced adsorption and energy storage. Nat. Commun. 2015, 6, 7221.

    Article  PubMed  PubMed Central  Google Scholar 

  2. Gu, C.; Huang, N.; Gao, J.; Xu, F.; Xu, Y.; Jiang, D. Controlled synthesis of conjugated microporous polymer films: versatile platforms for highly sensitive and label-free chemo-and biosensing. Angew. Chem. Int. Ed. 2014, 53(19), 4850–4855.

    Article  CAS  Google Scholar 

  3. Gu, C.; Chen, Y.; Zhang, Z.; Xue, S.; Sun, S.; Zhang, K.; Zhong, C.; Zhang, H.; Pan, Y.; Lv, Y.; Yang, Y.; Li, F.; Zhang, S.; Huang, F.; Ma, Y. Electrochemical route to fabricate film-like conjugated microporous polymers and application for organic electronics. Adv. Mater. 2013, 25(25), 3443–3448.

    Article  CAS  PubMed  Google Scholar 

  4. Yuan, S.; Dorney, B.; White, D.; Kirklin, S.; Zapol, P.; Yu, L.; Liu, D. J. Microporous polyphenylenes with tunable pore size for hydrogen storage. Chem. Commun. 2010, 46(25), 4547–4549.

    Article  CAS  Google Scholar 

  5. Bezzu, C. G.; Carta, M.; Tonkins, A.; Jansen, J. C.; Bernardo, P.; Bazzarelli, F.; McKeown, N. B. A spirobifluorene-based polymer of intrinsic microporosity with improved performance for gas separation. Adv. Mater. 2012, 24(44), 5930.

    Article  CAS  PubMed  Google Scholar 

  6. McKeown, N. B.; Budd, P. M. Polymers of intrinsic microporosity (PIMs): organic materials for membrane separations, heterogeneous catalysis and hydrogen storage. Chem. Soc. Rev. 2006, 35(8), 675–683.

    Article  CAS  PubMed  Google Scholar 

  7. 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. Conjugated microporous poly(aryleneethynylene) networks. Angew. Chem. Int. Ed. 2007, 46(45), 8574–8578.

    Article  Google Scholar 

  8. Ding, S. Y.; Wang, W. Covalent organic frameworks (COFs): from design to applications. Chem. Soc. Rev. 2013, 42(2), 548–568.

    Article  CAS  PubMed  Google Scholar 

  9. Li, B. Y.; Gong, R. N.; Wang, W.; Huang, X.; Zhang, W.; Li, H. M.; Hu, C. X.; Tan, B. E. A new strategy to microporous polymers: knitting rigid aromatic building blocks by external cross-linker. Macromolecules 2011, 44(8), 2410–2414.

    Article  CAS  Google Scholar 

  10. Ren, S. J.; Bojdys, M. J.; Dawson, R.; Laybourn, A.; Khimyak, Y. Z.; Adams, D. J.; Cooper, A. I. Porous, Fluorescent, Covalent triazine-based frameworks via room-temperature and microwave-assisted synthesis. Adv. Mater. 2012, 24(17), 2357–2361.

    Article  CAS  PubMed  Google Scholar 

  11. Tan, L.; Tan, B. Hypercrosslinked porous polymer materials: design, synthesis, and applications. Chem. Soc. Rev. 2017, 46(11), 3322–3356.

    Article  CAS  PubMed  Google Scholar 

  12. Li, L. N.; Ren, H.; Yuan, Y.; Yu, G. L.; Zhu, G. S. Construction and adsorption properties of porous aromatic frameworks via AlCl3-triggered coupling polymerization. J. Mater. Chem. A 2014, 2(29), 11091–11098.

    Article  CAS  Google Scholar 

  13. Xu, Y. H.; Jin, S. B.; Xu, H.; Nagai, A.; Jiang, D. L. Conjugated microporous polymers: design, synthesis and application. Chem. Soc. Rev. 2013, 42(20), 8012–8031.

    Article  CAS  PubMed  Google Scholar 

  14. Ghanem, B. S.; Msayib, K. J.; McKeown, N. B.; Harris, K. D. M.; Pan, Z.; Budd, P. M.; Butler, A.; Selbie, J.; Book, D.; Walton, A. A triptycene-based polymer of intrinsic microposity that displays enhanced surface area and hydrogen adsorption. Chem. Commun. 2007, (1), 67–69.

    Article  Google Scholar 

  15. Wang, S. L.; Tan, L. X.; Zhang, C. X.; Hussain, I.; Tan, B. E. Novel POSS-based organic-inorganic hybrid porous materials by low cost strategies. J. Mater. Chem. A 2015, 3(12), 6542–6548.

    Article  CAS  Google Scholar 

  16. Tian, Z. H.; Huang, J. J.; Zhang, Z. L.; Shao, G. L.; Liu, A.; Yuan, S. G. Organic-inorganic hybrid microporous polymers based on octaphenylcyclotetrasiloxane: synthesis, carbonization and adsorption for CO2. Microporous Mesoporous Mater. 2016, 234, 130–136.

    Article  CAS  Google Scholar 

  17. Zhu, J. H.; Chen, Q.; Sui, Z. Y.; Pan, L.; Yu, J. G.; Han, B. H. Preparation and adsorption performance of cross-linked porous polycarbazoles. J. Mater. Chem. A 2014, 2(38), 16181–16189.

    Article  CAS  Google Scholar 

  18. Msayib, K. J.; McKeown, N. B. Inexpensive polyphenylene network polymers with enhanced microporosity. J. Mater. Chem. A 2016, 4(26), 10110–10113.

    Article  CAS  Google Scholar 

  19. Meng, Q. B.; Weber, J. Lignin-based microporous materials as selective adsorbents for carbon dioxide separation. ChemSusChem 2014, 7(12), 3312–3318.

    Article  CAS  PubMed  Google Scholar 

  20. Modak, A.; Maegawa, Y.; Goto, Y.; Inagaki, S. Synthesis of 9,9′-spirobifluorene-based conjugated microporous polymers by FeCl3-mediated polymerization. Polym. Chem. 2016, 7(6), 1290–1296.

    Article  CAS  Google Scholar 

  21. Li, W.; Zhang, A.; Gao, H.; Chen, M.; Liu, A.; Bai, H.; Li, L. Massive preparation of pitch-based organic microporous polymers for gas storage. Chem. Commun. 2016, 52(13), 2780–2783.

    Article  CAS  Google Scholar 

  22. Gao, H.; Ding, L.; Bai, H.; Li, L. Microporous organic polymers based on hyper-crosslinked coal tar: preparation and application for gas adsorption. ChemSusChem 2017, 10(3), 618–623.

    Article  CAS  PubMed  Google Scholar 

  23. Li, B. Y.; Guan, Z. H.; Yang, X. J.; Wang, W. D.; Wang, W.; Hussain, I.; Song, K. P.; Tan, B. E.; Li, T. Multifunctional microporous organic polymers. J. Mater. Chem. A 2014, 2(30), 11930–11939.

    Article  CAS  Google Scholar 

  24. Gao, H.; Ding, L.; Bai, H.; Liu, A. H.; Li, S. Z.; Li, L. Pitchbased hyper-cross-linked polymers with high performance for gas adsorption. J. Mater. Chem. A 2016, 4(42), 16490–16498.

    Article  CAS  Google Scholar 

  25. Pan, L.; Chen, Q.; Zhu, J. H.; Yu, J. G.; He, Y. J.; Han, B. H. Hypercrosslinked porous polycarbazoles via one-step oxidative coupling reaction and Friedel-Crafts alkylation. Polym. Chem. 2015, 6(13), 2478–2487.

    Article  CAS  Google Scholar 

  26. Ben, T.; Li, Y.; Zhu, L.; Zhang, D.; Cao, D.; Xiang, Z.; Yao, X.; Qiu, S. Selective adsorption of carbon dioxide by carbonized porous aromatic framework (PAF). Energy Environ. Sci. 2012, 5(8), 8370–8376.

    Article  CAS  Google Scholar 

  27. Zhang, D.; Tao, L. M.; Wang, Q. H.; Wang, T. M. A facile synthesis of cost-effective triphenylamine-containing porous organic polymers using different crosslinkers. Polymer 2016, 82, 114–120.

    Article  CAS  Google Scholar 

  28. Luo, Y. L.; Zhang, S. C.; Ma, Y. X.; Wang, W.; Tan, B. Microporous organic polymers synthesized by self-condensation of aromatic hydroxymethyl monomers. Polym. Chem. 2013, 4(4), 1126–1131.

    Article  CAS  Google Scholar 

  29. Gao, H.; Ding, L.; Li, W. Q.; Ma, G. F.; Bai, H.; Li, L. Hypercross-linked organic microporous polymers based on alternating copolymerization of bismaleimide. ACS Macro Lett. 2016, 5(3), 377–381.

    Article  CAS  Google Scholar 

  30. Kou, J.; Sun, L. B. Fabrication of nitrogen-doped porous carbons for highly efficient CO2 capture: rational choice of a polymer precursor. J. Mater. Chem. A 2016, 4(44), 17299–17307.

    Article  CAS  Google Scholar 

  31. Rabbani, M. G.; El-Kaderi, H. M. Template-free Synthesis of a highly porous benzimidazole-linked polymer for CO2 capture and H2 storage. Chem. Mater. 2011, 23(7), 1650–1653.

    Article  CAS  Google Scholar 

  32. Martin, C. F.; Stoeckel, E.; Clowes, R.; Adams, D. J.; Cooper, A. I.; Pis, J. J.; Rubiera, F.; Pevida, C. Hypercrosslinked organic polymer networks as potential adsorbents for precombustion CO2 capture. J. Mater. Chem. 2011, 21(14), 5475–5483.

    Article  CAS  Google Scholar 

  33. Ren, X.; Li, H.; Chen, J.; Wei, L.; Modak, A.; Yang, H.; Yang, Q. N-doped porous carbons with exceptionally high CO2 selectivity for CO2 capture. Carbon 2017, 114, 473–481.

    Article  CAS  Google Scholar 

  34. Lin, Y.; Xiong, K.; Lu, Z.; Liu, S.; Zhang, Z.; Lu, Y.; Fu, R.; Wu, D. Functional nanonetwork-structured polymers and carbons with silver nanoparticle yolks for antibacterial application. Chem. Commun. 2017, 53(70), 9777–9780.

    Article  CAS  Google Scholar 

  35. Li, G.; Zhang, B.; Wang, Z. Facile synthesis of fluorinated microporous polyaminals for adsorption of carbon dioxide and selectivities over nitrogen and methane. Macromolecules 2016, 49(7), 2575–2581.

    Article  CAS  Google Scholar 

  36. Wang, Z. G.; Liu, X.; Wang, D.; Jin, J. Troger’s base-based copolymers with intrinsic microporosity for CO2 separation and effect of Troger’s base on separation performance. Polym. Chem. 2014, 5(8), 2793–2800.

    Article  CAS  Google Scholar 

  37. Yang, X.; Yao, S.; Yu, M.; Jiang, J. X. Synthesis and gas adsorption properties of tetra-armed microporous organic polymer networks based on triphenylamine. Macromol. Rapid Commun. 2014, 35(8), 834–839.

    Article  CAS  PubMed  Google Scholar 

  38. Zhu, Y.; Long, H.; Zhang, W. Imine-linked porous polymer frameworks with high small gas (H2, CO2, CH4, C2H2) uptake and CO2/N2 selectivity. Chem. Mater. 2013, 25(9), 1630–1635.

    Article  CAS  Google Scholar 

  39. Ashourirad, B.; Arab, P.; Verlander, A.; El-Kaderi, H. M. From azo-linked polymers to microporous heteroatom-doped carbons: tailored chemical and textural properties for gas separation. ACS Appl. Mater. Interfaces 2016, 8(13), 8491–8501.

    Article  CAS  PubMed  Google Scholar 

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Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (Nos. 51373143 and 21674087) and the Natural Science Foundation of Fujian Province (No. 2014J07002).

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Correspondence to Ping Lan or Lei Li.

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Tian, K., Zhu, TT., Lan, P. et al. Massive Preparation of Coumarone-indene Resin-based Hyper-crosslinked Polymers for Gas Adsorption. Chin J Polym Sci 36, 1168–1174 (2018). https://doi.org/10.1007/s10118-018-2127-6

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