Citation: Wang Zhitao, Li Hui, Yan Shichen, Fang Qianrong. Synthesis of a Two-dimensional Covalent Organic Framework with the Ability of Conducting Proton along Skeleton[J]. Acta Chimica Sinica, ;2020, 78(1): 63-68. doi: 10.6023/A19110397 shu

Synthesis of a Two-dimensional Covalent Organic Framework with the Ability of Conducting Proton along Skeleton

Wang Zhitao ^a,b ,
Li Hui ^a ,
Yan Shichen ^a ,
Fang Qianrong ^a,,

a.
State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, School of Chemistry, Jilin University, Changchun 130012, China
b.
School of Chemistry, Tonghua Normal College, Tonghua 134002, China

Corresponding author: Fang Qianrong, qrfang@jlu.edu.cn
Received Date: 7 November 2019
Available Online: 10 January 2019
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21571079)the National Natural Science Foundation of China 21571079

Figures(10)

Nitrogen heterocyclic compound like imidazole and triazole are often loaded in porous material for proton conduction. Inspired by this, we employ 5, 5'-diamino-3, 3'-bis(1H-1, 2, 4-triazole) (BTDA) containing triazole fragments in the structure as the construction unit to react with 2, 4, 6-triformylphloroglucinol (TFP) through Schiff-base condensation reaction to synthesize a novel two-dimensional covalent organic framework named TFP-BTDA-COF. The theoretical results were simulated using the Accelrys Material Studios 7.0 software package and compared with the powder X-ray diffraction (PXRD) test data to confirm the crystal structure of TFP-BTDA-COF. The porosity and pore structure of TFP-BTDA-COF were characterized by N₂ adsorption-desorption at 77 K. The condensation reaction was confirmed by Fourier transform infrared spectroscopy (FTIR). Due to the π-π accumulation of the 2D-COF, the N-H bond of the triazole in BTDA connecting unit is periodically and regularly arranged on each layer of the COF to form an ordered array. Under certain humidity conditions, the protons can be transmitted along the array in the one-dimensional pore channel by the intermediary of water molecules. Therefore, the TFP-BTDA-COF has the ability to conduct proton through the skeleton. The proton conductivity of TFP-BTDA-COF is tested by the AC impedance method. The results show that the proton conductivity of the material is gradually enhanced with the increase of the ambient humidity, and the maximum value is 1.4×10^-3 S·cm^-1 at 98% relative humidity. The PXRD of TFP-BTDA-COF in boiling water for 2 h and after 12 h AC impedance test were compared with the original experimental value to evaluate its tolerance under the working conditions of the proton membrane fuel cell. The PXRD diffraction peak intensity did not change obviously compared with that of the original experimental value. The thermogravimetric analysis results show that the thermal stability of TFP-BTDA-COF can reach high to 400℃. The above evidence proves that it has the potential to be used in proton membrane fuel cells.
- covalent organic framework,
- proton conduction,
- crystal structure,
- AC impedance
1. [1]
  Jacobson, M. Z.; Colella, W. G.; Golden, D. M. Science 2005, 308, 1901. doi: 10.1126/science.1109157
2. [2]
  Wang, Y.; Chen, K.; Mishler, J.; Cho, S. C.; Adroher, X. C. Appl. Energy 2011, 88, 981. doi: 10.1016/j.apenergy.2010.09.030
3. [3]
  He, X.-Y.; Gang, M.-Y.; He, G.-W.; Yin, Y.-H.; Cao, L.; Wu, H.; Jiang, Z.-Y. Chin. J. Chem. 2017, 35, 673. doi: 10.1002/cjoc.201600577
4. [4]
  Chen, X.; Yan, H.-J.; Xia, D.-G. Acta Chim. Sinica 2017, 75, 189. doi: 10.3969/j.issn.0253-2409.2017.02.008
5. [5]
  Cui, L.-R.; Zhang, J.; Sun, Y.-Y.; Lu, S.-F.; Xiang, Y. Acta Chim. Sinica 2019, 77, 47. doi: 10.7503/cjcu20180421
6. [6]
  Zhong, G.-Y.; Wang, H.-J.; Yu, H.; Peng, F. Acta Chim. Sinica 2017, 75, 943.
7. [7]
  Zhang, H.-W.; Shen, P.-K. Chem. Rev. 2012, 112, 2780. doi: 10.1021/cr200035s
8. [8]
  Mauritz, K. A.; Moore, R. B. Chem. Rev. 2004, 104, 4535. doi: 10.1021/cr0207123
9. [9]
  Nasef, M. M. Chem. Rev. 2014, 114, 12278. doi: 10.1021/cr4005499
10. [10]
  Shimizu, G. K. H.; Taylor, J. M.; Kim, S. Science 2013, 341, 354. doi: 10.1126/science.1239872
11. [11]
  Yoon, M.; Suh, K.; Natarajan, S.; Kim, K. Angew. Chem., Int. Ed. 2013, 52, 2688. doi: 10.1002/anie.201206410
12. [12]
  Yamada, T.; Otsubo, K.; Makiura, R.; Kitagawa, H. Chem. Soc. Rev. 2013, 42, 6655. doi: 10.1039/c3cs60028a
13. [13]
  Ramaswamy, P.; Wong, N. E.; Shimizu, G. K. H. Chem. Soc. Rev. 2014, 43, 5913. doi: 10.1039/C4CS00093E
14. [14]
  Matoga, D.; Oszajca, M.; Molenda, M. Chem. Commun. 2015, 51, 7637. doi: 10.1039/C5CC01789K
15. [15]
  Tang, Q.; Liu, Y.-W.; Liu, S.-X.; He, D.-F.; Miao, J.; Wang, X.-Q.; Yang, G.-C. J. Am. Chem. Soc. 2014, 136, 12444. doi: 10.1021/ja5069855
16. [16]
  Côté, A. P.; Benin, A. I.; Ockwig, N. W.; O'Keeffe, M.; Matzger, A. J.; Yaghi, O. M. Science 2005, 310, 1166. doi: 10.1126/science.1120411
17. [17]
  Ding, S.-Y.; Wang, W. Chem. Soc. Rev. 2013, 42, 548. doi: 10.1039/C2CS35072F
18. [18]
  Waller, P. J.; Gándara, F.; Yaghi, O. M. Acc. Chem. Res. 2015, 48, 3053. doi: 10.1021/acs.accounts.5b00369
19. [19]
  Chen, Q.-D.; Tang, J.-J.; Fang, Q.-R. Chem. J. Chin. Univ. 2018, 39, 2357. doi: 10.7503/cjcu20180190
20. [20]
  Zheng, C.-N.; Zhu, J.-H.; Yang, C.-Q.; Lu, C.-B.; Chen, Z.-Y.; Zhuang, X.-D. Sci. China Chem. 2019, 62, 1145. doi: 10.1007/s11426-019-9477-y
21. [21]
  Yuan, F.-Y.; Tan, J.; Guo, J. Sci. China Chem. 2018, 61, 143. doi: 10.1007/s11426-017-9162-3
22. [22]
  Huang, N.; Chen, X.; Krishna, R.; Jiang, D.-L. Angew. Chem., Int. Ed. 2015, 54, 2986. doi: 10.1002/anie.201411262
23. [23]
  Dogru, M.; Handloser, M.; Auras, F.; Kunz, T.; Medina, D.; Hartschuh, A.; Knochei, P.; Bein, T. Angew. Chem., Int. Ed. 2013, 52, 2920. doi: 10.1002/anie.201208514
24. [24]
  Cai, P.-W.; Peng, X.-X.; Huang, J.-H.; Jia, J.-C.; Hu, X.; Wen, Z.-H. Sci. China Chem. 2019, 62, 385. doi: 10.1007/s11426-018-9395-1
25. [25]
  Pang, C.-M.; 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.
26. [26]
  Peng, Z.-K.; Ding, H.-M.; Chen, R.-F.; Gao, C.; Wang, C. Acta Chim. Sinica 2019, 77, 681.
27. [27]
  Chandra, S.; Kundu, T.; Kandambeth, S.; Babarao, R.; Marathe, Y.; Kunjir, S. M.; Banerjee, R. J. Am. Chem. Soc. 2014, 136, 6570. doi: 10.1021/ja502212v
28. [28]
  Xu, H.; Tao, S.-S.; Jiang, D. L. Nat. Mater. 2016, 15, 722. doi: 10.1038/nmat4611
1. [1]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
2. [2]
  Fan Wu , Wenchang Tian , Jin Liu , Qiuting Zhang , YanHui Zhong , Zian Lin . Core-Shell Structured Covalent Organic Framework-Coated Silica Microspheres as Mixed-Mode Stationary Phase for High Performance Liquid Chromatography. University Chemistry, 2024, 39(11): 319-326. doi: 10.12461/PKU.DXHX202403031
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  Qiuting Zhang , Fan Wu , Jin Liu , Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
14. [14]
  Yongzhi LI , Han ZHANG , Gangding WANG , Yanwei SUI , Lei HOU , Yaoyu WANG . A two-dimensional metal-organic framework for the determination of nitrofurantoin and nitrofurazone in aqueous solution. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 245-253. doi: 10.11862/CJIC.20240307
15. [15]
  Fei Xie , Chengcheng Yuan , Haiyan Tan , Alireza Z. Moshfegh , Bicheng Zhu , Jiaguo Yu . d带中心调控过渡金属单原子负载COF吸附O₂的理论计算研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2407013-. doi: 10.3866/PKU.WHXB202407013
16. [16]
  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
17. [17]
  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
18. [18]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
19. [19]
  Jinfeng Chu , Lan Jin , Yu-Fei Song . Exploration and Practice of Flipped Classroom in Inorganic Chemistry Experiment: a Case Study on the Preparation of Inorganic Crystalline Compounds. University Chemistry, 2024, 39(2): 248-254. doi: 10.3866/PKU.DXHX202308016
20. [20]
  Yuyao Wang , Zhitao Cao , Zeyu Du , Xinxin Cao , Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100035-. doi: 10.3866/PKU.WHXB202406014

Get Citation

PDF

XML

Metrics

PDF Downloads(41)
Abstract views(2048)
HTML views(507)

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