Citation: Ke Tian, Ting-Ting Zhu, Ping Lan, Zheng-Chen Wu, Wei Hu, Fei-Fei Xie, Lei Li. Massive Preparation of Coumarone-indene Resin-based Hyper-crosslinked Polymers for Gas Adsorption[J]. Chinese Journal of Polymer Science, ;2018, 36(10): 1168-1174. doi: 10.1007/s10118-018-2127-6 shu

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

Ke Tian ¹ ,
Ting-Ting Zhu ¹ ,
Ping Lan ^2,, ,
Zheng-Chen Wu ¹ ,
Wei Hu ¹ ,
Fei-Fei Xie ¹ ,
Lei Li ^1,,

a.
College of Materials and Fujian Provincial Key Laboratory of Materials Genome, Xiamen University, Xiamen 361005, China
b.
Material and Textile College, Jiaxing University, Jiaxing 314000, China

Corresponding author: Ping Lan, lanping007@126.com (P.L.) Lei Li, lilei@xmu.edu.cn (L.L.)
Received Date: 4 January 2018
Revised Date: 4 January 2018
Accepted Date: 13 February 2018
Available Online: 28 March 2018

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.
- Coumarone-indene resin,
- Friedel-Crafts alkylation,
- Gas adsorption,
- Microporous organic polymers
1. [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 doi: 10.1038/ncomms8221
2. [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 doi: 10.1002/anie.201402141
3. [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 doi: 10.1002/adma.v25.25
4. [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 doi: 10.1039/c0cc00235f
5. [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 doi: 10.1002/adma.v24.44
6. [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 doi: 10.1039/b600349d
7. [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 doi: 10.1002/anie.200701595
8. [8]
  Ding, S. Y.; Wang, W. Covalent organic frameworks (COFs): from design to applications. Chem. Soc. Rev. 2013, 42(2), 548−568 doi: 10.1039/C2CS35072F
9. [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 doi: 10.1021/ma200630s
10. [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 doi: 10.1002/adma.201200751
11. [11]
  Tan, L.; Tan, B. Hypercrosslinked porous polymer materials: design, synthesis, and applications. Chem. Soc. Rev. 2017, 46(11), 3322−3356 doi: 10.1039/C6CS00851H
12. [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 doi: 10.1039/C4TA01252F
13. [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 doi: 10.1039/c3cs60160a
14. [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 doi: 10.1039/B614214A
15. [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 doi: 10.1039/C4TA06963C
16. [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 doi: 10.1016/j.micromeso.2016.06.038
17. [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 doi: 10.1039/C4TA01537A
18. [18]
  Msayib, K. J.; McKeown, N. B. Inexpensive polyphenylene network polymers with enhanced microporosity. J. Mater. Chem. A 2016, 4(26), 10110−10113 doi: 10.1039/C6TA03257E
19. [19]
  Meng, Q. B.; Weber, J. Lignin-based microporous materials as selective adsorbents for carbon dioxide separation. ChemSusChem 2014, 7(12), 3312−3318 doi: 10.1002/cssc.v7.12
20. [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 doi: 10.1039/C5PY01900A
21. [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 doi: 10.1039/C5CC07908J
22. [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 doi: 10.1002/cssc.v10.3
23. [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 doi: 10.1039/C4TA01081G
24. [24]
  Gao, H.; Ding, L.; Bai, H.; Liu, A. H.; Li, S. Z.; Li, L. Pitch-based hyper-cross-linked polymers with high performance for gas adsorption. J. Mater. Chem. A 2016, 4(42), 16490−16498 doi: 10.1039/C6TA07033G
25. [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 doi: 10.1039/C4PY01797H
26. [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 doi: 10.1039/c2ee21935b
27. [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 doi: 10.1016/j.polymer.2015.11.041
28. [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 doi: 10.1039/C2PY20914D
29. [29]
  Gao, H.; Ding, L.; Li, W. Q.; Ma, G. F.; Bai, H.; Li, L. Hyper-cross-linked organic microporous polymers based on alternating copolymerization of bismaleimide. ACS Macro Lett. 2016, 5(3), 377−381 doi: 10.1021/acsmacrolett.6b00015
30. [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 doi: 10.1039/C6TA07305K
31. [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 doi: 10.1021/cm200411p
32. [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 pre-combustion CO₂ capture. J. Mater. Chem. 2011, 21(14), 5475−5483 doi: 10.1039/c0jm03534c
33. [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 doi: 10.1016/j.carbon.2016.12.056
34. [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 doi: 10.1039/C7CC04621A
35. [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 doi: 10.1021/acs.macromol.6b00147
36. [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 doi: 10.1039/c3py01608k
37. [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 doi: 10.1002/marc.v35.8
38. [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 doi: 10.1021/cm400019f
39. [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 doi: 10.1021/acsami.6b00567
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