Citation: Fu Jingru, Ben Teng. Fabrication of a Novel Covalent Organic Framework Membrane and Its Gas Separation Performance[J]. Acta Chimica Sinica, ;2020, 78(8): 805-814. doi: 10.6023/A20040128 shu

Fabrication of a Novel Covalent Organic Framework Membrane and Its Gas Separation Performance

Fu Jingru ,
Ben Teng ^,

College of Chemistry, Jilin University, Changchun 130012

Corresponding author: Ben Teng, tben@jlu.edu.cn
Received Date: 28 April 2020
Available Online: 9 June 2020
Fund Project: the Science and Technology Department of Jilin Province Foundation 20180414009GHthe National Natural Science Foundation of China 21871103"111" Project BP0719036Project supported by the National Natural Science Foundation of China (Nos. 91956108, 21871103), "111" Project (No. BP0719036) and the Science and Technology Department of Jilin Province Foundation (No. 20180414009GH)the National Natural Science Foundation of China 91956108

Figures(14)

Herein, we employ 2, 5-dimethoxyterephthalaldehyde (DMTA) containing ether oxygen group in the structure as the construction unit to react with tetra-(4-anilyl)-methane (TAM) through Schiff-based condensation reaction in a Teflon-lined autoclave to synthesize a novel three-dimensional covalent organic framework named DMTA-COF. Furthermore, the condensation reaction was confirmed by Fourier transform infrared spectroscopy (FT-IR). The crystal structure of DMTA-COF was analyzed by the powder X-ray diffraction (PXRD) measurement in conjunction with structural simulation. The morphology, thermal stability, porosity and pore distribution of DMTA-COF were measured by scanning electron microscopy (SEM), thermogravimetric analysis (TGA), and N₂ adsorption-desorption at 77 K. The high affinity for CO₂ adsorption was also confirmed by low pressure CO₂ sorption. Considering the relatively small pore size and the strong CO₂ adsorption interaction of DMTA-COF due to an abundant of ether oxygen group and imine linkage, we synthesized one continuous supported DMTA-COF membrane for H₂/CO₂ separation. In our study, the porous Al₂O₃ support surface was first coated with polyaniline (PANI) and was then further functionalized with aldehyde groups by reaction with DMTA at 150 ℃ for 1 h. Finally, in situ growth of the COF membrane utilizing the covalent linkage yielded a novel continuous DMTA-COF membrane. X-ray diffraction (XRD) result indicated that the DMTA-COF membrane was pure phase and had high crystallinity. From SEM characterization, we could see that the DMTA-COF membrane was compact and well intergrowth and adhered to the support tightly. Gas separation performance results shown that DMTA-COF membrane had a high H₂ permeance and selectivity of H₂/CO₂. For DMTA-COF membrane, the 1:1 binary mixture gas separation factors of H₂/CO₂ calculated as the gas molar ratios in permeate and retentate side was 8.3 at room temperature and atmospheric pressure. And H₂/CO₂ separation factor of DMTA-COF membrane exceeded the corresponding Knudsen coefficient (4.7), with H₂ permeance of up to 6.3×10^－7 mol·m^－2·s^－1·Pa^－1. Because of its outstanding characteristics, the novel DMTA-COF membrane is expected to be widely used in the field of H₂ purification and separation.
- covalent organic framework,
- crystal structure,
- membranes,
- gas separation,
- H₂ purification
1. [1]
  Koros, W. J.; Zhang, C. Nat. Mater. 2017, 16, 289. doi: 10.1038/nmat4805
2. [2]
  Huang, A.-S.; Liang, F.-Y.; Steinbach, F.; Caro. J. J. Membr. Sci. 2010, 350, 5. doi: 10.1016/j.memsci.2009.12.029
3. [3]
  Huang, A.-S.; Caro, J. J. Mater. Chem. 2011, 21, 11424. doi: 10.1039/c1jm11549a
4. [4]
  Shi, K.-Y.; Chi, Y.-J.; Jin, X.-Q.; Xu, M.; Yuan, F.-L.; Fu, H.-G. Acta Chim. Sinica 2005, 63, 885.
5. [5]
  Huang, A.-S.; Wang, N.-Y.; Kong, C.-L.; Caro, J. Angew. Chem. Int. Ed. 2012, 51, 10551. doi: 10.1002/anie.201204621
6. [6]
  Ben, T.; Lu, C.-J.; Pei, C.-Y.; Xu, S.-X.; Qiu, S.-L. Chem. Eur. J. 2012, 18, 10250. doi: 10.1002/chem.201201574
7. [7]
  Liu, B.; Tang, L.-X.; Lian, Y.-H.; Li, Z.; Sun, C.-Y.; Chen, G.-J. Acta Chim. Sinica 2013, 71, 920.
8. [8]
  Guo, H.-L.; Zhu, G.-S.; Hewitt, I. J.; Qiu, S.-L. J. Am. Chem. Soc. 2009, 131, 1646. doi: 10.1021/ja8074874
9. [9]
  Budd, P. M.; Msayib, K. J.; Tattershall, C. E.; Ghanem, B. S.; Reynolds, K. J.; McKeown, N. B.; Fritsch, D. J. Membr. Sci. 2005, 251, 263. doi: 10.1016/j.memsci.2005.01.009
10. [10]
  Diercks, C. S.; Yaghi, O. M. Science 2017, 355, 6328.
11. [11]
  Chen, Q.-D.; Tang, J.-J.; Fang, Q.-R. Chem. J. Chin. Univ. 2018, 39, 2357.
12. [12]
  Huang, N.; Wang, P.; Jiang, D.-L. Nat. Rev. Mater. 2016, 1, 16068. doi: 10.1038/natrevmats.2016.68
13. [13]
  Wang, Z.-T.; Li, H.; Yan, S.-C.; Fang, Q.-R. Acta Chim. Sinica 2020, 78, 63.
14. [14]
  Huang, W.; Li, Y.-G. Chin. J. Chem. 2019, 37, 1291. doi: 10.1002/cjoc.201900375
15. [15]
  Peng, Z.-K.; Ding, H.-M.; Chen, R.-F.; Gao, C.; Wang, C. Acta Chim. Sinica 2019, 77, 681.
16. [16]
  Dong, G.-X.; Lee, Y. M. J. Mater. Chem. A 2017, 5, 13294. doi: 10.1039/C7TA04015F
17. [17]
  Yuan, S.-S.; Li, X.; Zhu, J.-Y.; Zhang, G.; Puyvelde, P. V.; Bruggen, B. V. Chem. Soc. Rev. 2019, 48, 2665. doi: 10.1039/C8CS00919H
18. [18]
  Wang, J.; Zhu, J.-Y.; Zhang, Y.-T.; Liu, J.-D.; Bruggen, B. V. Nanoscale 2017, 9, 2942. doi: 10.1039/C6NR08417F
19. [19]
  Ding, S.-Y.; Wang, W. Chem. Soc. Rev. 2013, 42, 548. doi: 10.1039/C2CS35072F
20. [20]
  Uribe-Romo, F. J.; Doonan, C. J.; Furukawa, H.; Oisaki, K.; Yaghi, O. M. J. Am. Chem. Soc. 2011, 133, 11478. doi: 10.1021/ja204728y
21. [21]
  Kandambeth, Sharath.; Mallick, A.; Lukose, B.; Mane, M. V.; Heine, T.; Rahul, B. J. Am. Chem. Soc. 2012, 134, 19524. doi: 10.1021/ja308278w
22. [22]
  Zhou, H.-C.; Long, J.-R.; Yaghi, O. M. Chem. Rev. 2012, 112, 673. doi: 10.1021/cr300014x
23. [23]
  Chung, T. S.; Jiang, L.-Y.; Li, Y.; Kulprathipanja, S. Prog. Polym. Sci. 2007, 32, 483. doi: 10.1016/j.progpolymsci.2007.01.008
24. [24]
  Bunck, D. N.; Dichtel, W. R. J. Am. Chem. Soc. 2013, 135, 14952. doi: 10.1021/ja408243n
25. [25]
  Liu, X.-H.; Guan, C.-Z.; Ding, S.-Y.; Wang, W.; Yan, H.-Y.; Wang, D.; Wan, L.-J. J. Am. Chem. Soc. 2013, 135, 28, 10470.
26. [26]
  Dai, W.-Y.; Shao, F.; Szczerbiński, J.; McCaffrey, R.; Zenobi, R.; Jin, Y.-H.; Schlüter, D.; Zhang, W. Angew. Chem., Int. Ed. 2016, 55, 213. doi: 10.1002/anie.201508473
27. [27]
  Dey, K.; Pal, M.; Rout, K. C.; Kunjattu-H, S.; Das, A.; Mukherjee, R.; Kharul, U. K.; Baneriee, R. J. Am. Chem. Soc. 2017, 139, 13083. doi: 10.1021/jacs.7b06640
28. [28]
  Fu, J.-R.; Das, S.; Xing, G.-L.; Ben, T.; Valtchev, V.; Qiu, S.-L. J. Am. Chem. Soc. 2016, 138, 7673. doi: 10.1021/jacs.6b03348
29. [29]
  Fan, H.-W.; Mundstock, A.; Feldhoff, A.; Knebel, A.; Gu, J.-H.; Meng, H.; Caro, J. J. Am. Chem. Soc. 2018, 140, 10094. doi: 10.1021/jacs.8b05136
30. [30]
  Fan, H.-W.; Mundstock, A.; Gu, J.-H.; Meng, H.; Caro, J. J. Mater. Chem. A. 2018, 6, 16849. doi: 10.1039/C8TA05641B
31. [31]
  Segura, J. L.; Mancheo, M. J.; Zamora, F. Chem. Soc. Rev. 2016, 45, 5635. doi: 10.1039/C5CS00878F
32. [32]
  Ma, Y.-X.; Li, Z.-J.; Wei, L.; Ding, S.-Y.; Zhang, Y.-B.; Wang, W. J. Am. Chem. Soc. 2017, 139, 4995. doi: 10.1021/jacs.7b01097
33. [33]
  Zhang, Y.-B.; Su, J.; Furukawa, H.; Yun, Y.-F.; Gándara, F.; Duong, A.; Zou, X.-D.; Yaghi, O. M. J. Am. Chem. Soc. 2013, 135, 16336. doi: 10.1021/ja409033p
34. [34]
  Bureekaew, S.; Sato, H.; Matsuda, R.; Kubota, Y.; Hirose, R.; Kim, J.; Kato, K.; Takata, M.; Kitagawa, S. Angew. Chem., Int. Ed. 2010, 49, 7660. doi: 10.1002/anie.201002259
35. [35]
  Reichenbach, C.; Kalies, G.; Lincke, J.; Lässig, D, ; Krautscheid, H.; Moellmer, J.; Thommes, M. Microporous Mesoporous Mater. 2011, 142, 592. doi: 10.1016/j.micromeso.2011.01.005
36. [36]
  Feng, S.-C.; Ren, J.-Z.; Li, H.; Hua, K.-S.; Li, X.-X.; Deng, M.-C. Membr. Sci. Technol. 2013, 33, 53.
37. [37]
  Lin, H.-Q.; Freeman, B. D. J. Mol. Struct. 2005, 739, 57. doi: 10.1016/j.molstruc.2004.07.045
38. [38]
  Lu, H.; Wang, C.; Chen, J.-J.; Ge, R.-L.; Leng, W.-G.; Dong, B.; Huang, J.; Gao, Y.-N. Chem. Commun. 2015, 51, 15562. doi: 10.1039/C5CC06742A
39. [39]
  Robeson, L. M. J. Membr. Sci. 2008, 320, 390. doi: 10.1016/j.memsci.2008.04.030
1. [1]
  Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
2. [2]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
3. [3]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
4. [4]
  Xiaoqi LAN , Wei LI , Long JING , Mengyu SU , Xiaoling LUO , Zheng LIU , Qun TANG . Synthesis, crystal structure, and spectral properties of transition-metal-organic frameworks based on thiophene carboxylic acid ligands. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 309-316. doi: 10.11862/CJIC.20250212
5. [5]
  Xuhu GUO , Chuntao ZHANG , Jinshu LI , Yuanyuan TAN , Qaiowen CHANG , Juan YU . Structure and catalytic performance of [Pd(1, 5-cyclooctadiene)X₂] (X=Cl, Br) modulated by organophosphine ligands. Chinese Journal of Inorganic Chemistry, 2026, 42(6): 1247-1260. doi: 10.11862/CJIC.20250299
6. [6]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
7. [7]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
8. [8]
  Wenjuan SHI , Yuke LU , Xiuyuan LI , Lei HOU , Yaoyu WANG . Mg(Ⅱ) metal-organic frameworks based on biphenyltetracarboxylic acid: Synthesis and CO₂ adsorption and catalytic conversion performance. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2455-2463. doi: 10.11862/CJIC.20250220
9. [9]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
10. [10]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
11. [11]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
12. [12]
  Xiaogang YANG , Xinya ZHANG , Jing LI , Huilin WANG , Min LI , Xiaotian WEI , Xinci WU , Lufang MA . Synthesis, structure, and photoelectric properties of Zinc(Ⅱ)-triphenylamine based metal-organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2078-2086. doi: 10.11862/CJIC.20250167
13. [13]
  Yan Liu , Yuexiang Zhu , Luhua Lai . Introduction to Blended and Small-Class Teaching in Structural Chemistry: Exploring the Structure and Properties of Crystals. University Chemistry, 2024, 39(3): 1-4. doi: 10.3866/PKU.DXHX202306084
14. [14]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
15. [15]
  Weina Wang , Fengyi Liu , Wenliang Wang . “Extracting Commonality, Delving into Typicals, Deriving Individuality”: Constructing a Knowledge Graph of Crystal Structures. University Chemistry, 2024, 39(3): 36-42. doi: 10.3866/PKU.DXHX202308029
16. [16]
  Junqiao Zhuo , Xinchen Huang , Qi Wang . Symbol Representation of the Packing-Filling Model of the Crystal Structure and Its Application. University Chemistry, 2024, 39(3): 70-77. doi: 10.3866/PKU.DXHX202311100
17. [17]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
18. [18]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
19. [19]
  Hongjie SHEN , Haozhe MIAO , Yuhe YANG , Yinghua LI , Deguang HUANG , Xiaofeng ZHANG . Synthesis, crystal structure, and fluorescence properties of two Cu(Ⅰ) complexes based on pyridyl ligand. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 855-863. doi: 10.11862/CJIC.20250009
20. [20]
  Wenyan Dan , Weijie Li , Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060

Get Citation

PDF

XML

Metrics

PDF Downloads(37)
Abstract views(3912)
HTML views(757)

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