Citation: Xu Jiawei, Zhang Chong, Wang Xunchang, Jiang Jiaxing, Wang Feng. Synthesis and Gas Sorption Properties of Microporous Poly(arylene ethynylene) Frameworks[J]. Acta Chimica Sinica, ;2017, 75(5): 473-478. doi: 10.6023/A17020068 shu

Synthesis and Gas Sorption Properties of Microporous Poly(arylene ethynylene) Frameworks

Xu Jiawei ^a ,
Zhang Chong ^b ,
Wang Xunchang ^a ,
Jiang Jiaxing ^b,*,, ,
Wang Feng ^a,*,,

a.
School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan 430073
b.
School of Materials Science and Engineering, Shaanxi Normal University, Xi'an 710062

Corresponding author: Jiang Jiaxing, jiaxing@snnu.edu.cn Wang Feng, psfwang@wit.edu.cn
Received Date: 17 February 2017

Fund Project: the Education Ministry of China NCET-12-0714the the Natural Science Foundation of China 51103111

Figures(6)

Microporous organic polymers (MOPs) have drawn much attention because of their potential applications such as gas storage, separation and heterogeneous catalysis. There is great interest in the design, synthesis and property evaluation of poly(arylene ethynylenes) (PAEs) with intrinsic microporosity. In addition to Sonogashira coupling reaction between terminal alkynes and halides, the oxidative dimerization of terminal alkynes is an alternating strategy for the buildup of the microporous PAE frameworks. In this paper, a series of MOPs were synthesized by the oxidative dimerization of terminal alkynes using triethynyl monomers such as tris(4-ethynylphenyl)amine, tris(4-ethynylphenyl)methylsilane and polytris(4-ethynylphenyl)phenylsilane. The resulting MOPs were characterized by FT-IR spectra, thermogravimetric analysis (TGA), scanning electron microscopy (SEM), transmission electron microscopy (TEM), powder X-ray diffraction (PXRD) measurements. FT-IR spectra indicate the success of the homocoupling reaction for constructing the dialkyne-bridged polymer frameworks. These polymer frameworks exhibit high thermal stability with onset of decomposition temperature above 350 ℃ at 5% mass loss under nitrogen flow. PXRD and TEM measurements revealed that all the polymer frameworks are amorphous solid in nature. These dialkyne-bridged MOPs exhibit moderate surface areas ranging from 602 to 715 m²·g^-1. The incorporation of triphenylamine moieties into the polymer skeleton increases the number of electron donating basic nitrogen sites in the porous frameworks. Thus, the triphenylamine-based polymer polytris(4-ethynylphenyl)amine (TEPA-MOP) with the highest Brunauer-Emmett-Teller (BET) surface area shows the highest CO₂ uptake capacity of 1.59 mmol·g^-1 at 273 K and 1.13 bar among the resulting polymer frameworks. In addition, TEPA-MOP showed the highest H₂ adsorption up to 1.04 wt% at 1.13 bar and 77 K and polytris(4-ethynylphenyl)phenylsilane (TEPP-MOP) displayed the lowest H₂ adsorption of 0.64 wt% at the same conditions. As for separation of CO₂, both TEPA-MOP and TEPP-MOP exhibit relatively high CO₂-over-N₂ selectivities of 69.9 and 73.2 at 273 K, respectively. The above results show that TEPA-MOP might be the good candidate for the balanced CO₂ uptake capacity with impressive CO₂/N₂ selectivity among the microporous PAE frameworks.
- microporous organic polymer,
- poly(arylene ethynylene),
- oxidative dimerization,
- gas adsorption,
- separation
1. [1]
  Monastersky, R. Nature 2013, 497, 13. doi: 10.1038/497013a
2. [2]
  Wu, Z. K.; Huang, Z. L.; Zhang, Y.; Qin, Y. H.; Ma, J. Y.; Luo, Y. B. Chem. Eng. J. 2016, 295, 64. doi: 10.1016/j.cej.2016.03.030
3. [3]
  Wang, T. L.; Jens, K. J. Int. J. Greenh. Gas Con. 2015, 37, 354. doi: 10.1016/j.ijggc.2015.03.017
4. [4]
  Luo, C.; Zheng, Y.; Guo, J.; Feng, B. Fuel 2014, 127, 124. doi: 10.1016/j.fuel.2013.09.063
5. [5]
  Dawson, R.; Cooper, A. I.; Adams, D. J. Prog. Polym. Sci. 2012, 37, 530. doi: 10.1016/j.progpolymsci.2011.09.002
6. [6]
  Tan, L. X.; Tan, B. Chem. Soc. Rev. 2017, DOI: 10.1039/ c6cs00851h. doi: 10.1039/c6cs00851h
7. [7]
  Das, S.; Heasman, P.; Ben, T.; Qiu, S. L. Chem. Rev. 2017, 117, 1515. doi: 10.1021/acs.chemrev.6b00439
8. [8]
  Cooper, A. I. Adv. Mater. 2009, 21, 1291. doi: 10.1002/adma.v21:12
9. [9]
  Jiang, J. X.; Cooper, A. I. Top. Curr. Chem. 2010. 293, 1.
10. [10]
  Xu, Y. H.; Jin, S. B.; Xu, H.; Nagai, A.; Jiang, D. L. Chem. Soc. Rev. 2013, 42, 8012. doi: 10.1039/c3cs60160a
11. [11]
  Budd, P. M.; Ghanem, B. S.; Makhseed, S.; McKeown, N. B.; Msayib, K. J.; Tattershall, C. E. Chem. Commun. 2004, 230.
12. [12]
  McKeown, N. B.; Budd, P. M. Macromolecules 2010, 43, 5163. doi: 10.1021/ma1006396
13. [13]
  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
14. [14]
  Ding, S. Y.; Wang, W. Chem. Soc. Rev. 2013, 42, 548.
15. [15]
  Feng, X.; Ding, X. S.; Jiang, D. L. Chem. Soc. Rev. 2012, 41, 6010. doi: 10.1039/c2cs35157a
16. [16]
  Tan, L. X.; Tan, B. Acta Chim. Sinica 2015, 73, 530. doi: 10.3969/j.issn.0253-2409.2015.05.003
17. [17]
  Xu, S. J.; Luo, Y. L.; Tan, B. Macromol. Rapid. Commun. 2013, 34, 471. doi: 10.1002/marc.v34.6
18. [18]
  Luo, Y.; Li, B.; Wang, W.; Wu, K.; Tan, B. Adv. Mater. 2012, 24, 5703. doi: 10.1002/adma.v24.42
19. [19]
  Ren, S. J.; Bojdys, M. J.; Dawson, R.; Laybourn, A.; Khimyak, Y. Z.; Adams, D. J.; Cooper, A. I. Adv. Mater. 2012, 24, 2357. doi: 10.1002/adma.201200751
20. [20]
  Ben, T.; Ren, H.; Ma, S. Q.; Cao, D. P.; Lan, J. H.; Jing, X. F.; Wang, W. C.; Xu, J.; Deng, F.; Simmons, J. M.; Qiu, S. L.; Zhu, G. S. Angew. Chem., Int. Ed. 2009, 48, 9457. doi: 10.1002/anie.200904637
21. [21]
  Yuan, Y.; Yan, Z. J.; Ren, H.; Liu, Q. Y.; Zhu, G. S.; Sun, F. X. Acta Chim. Sinica 2012, 70, 1446.
22. [22]
  Jiang, J. X.; Su, F. B.; Trewin, A.; Wood, C. D.; Campbell, N. L.; Niu, H. J.; Dickinson, C.; Ganin, A. Y.; Rosseinsky, M. J.; Khimyak, Y. Z.; Cooper, A. I. Angew. Chem., Int. Ed. 2007, 46, 8574. doi: 10.1002/anie.v46:45
23. [23]
  Jiang, J. X.; Su, F. B.; Trewin, A.; Wood, C. D.; Niu, H. J.; Jones, J. T.; Khimyak, Y. Z.; Cooper, A. I. J. Am. Chem. Soc. 2008, 130, 7710. doi: 10.1021/ja8010176
24. [24]
  Jiang, J. X.; Su, F. B.; Niu, H. J.; Wood, C. D.; Campbell, N. L.; Khimyak, Y. Z.; Cooper, A. I. Chem. Commun. 2008, 486.
25. [25]
  Jiang, J. X.; Trewin, A.; Su, F. B.; Wood, C. D.; Niu, H. J.; Jones, J. T. A.; Khimyak, Y. Z.; Cooper, A. I. Macromolecules 2009, 42, 2658. doi: 10.1021/ma802625d
26. [26]
  Ma, H. P.; Ren, H.; Zou, X. Q.; Sun, F. X.; Yan, Z. J.; Cai, K.; Wang, D. Y.; Zhu, G. S. J. Mater. Chem. A 2013, 1, 752. doi: 10.1039/C2TA00616B
27. [27]
  Yuan, R. R.; Ren, H.; Yan, Z. J.; Wang, A. F.; Zhu, G. S. Polym. Chem. 2014, 5, 2266. doi: 10.1039/c3py01252b
28. [28]
  Yan, Z. J.; Yuan, Y.; Tian, Y. Y.; Zhang, D. M.; Zhu, G. S. Angew. Chem., Int. Ed. 2015, 54, 12733. doi: 10.1002/anie.201503362
29. [29]
  Ma, H. P.; Ren, H.; Zou, X. Q.; Meng, S.; Sun, F. X.; Zhu, G. S. Polym. Chem. 2014, 5, 144. doi: 10.1039/C3PY00647F
30. [30]
  Yang, Z. Z.; Zhao, Y. F.; Zhang, H. Y.; Yu, B.; Ma, Z. S.; Ji, G. P.; Liu, Z. M. Chem. Commun. 2014, 50, 13910. doi: 10.1039/C4CC06423B
31. [31]
  Thompson, C. M.; McCandless, G. T.; Wijenayake, S. N.; Alfarawati, O.; Jahangiri, M.; Kokash, A.; Tran, Z.; Smaldone, R. A. Macromolecules 2014, 47, 8645. doi: 10.1021/ma501663j
32. [32]
  Thompson, C. M.; Li, F.; Smaldone, R. A. Chem. Commun. 2014, 50, 6171. doi: 10.1039/c4cc02213k
33. [33]
  Trunk, M.; Herrmann, A.; Bildirir, H.; Yassin, A.; Schmidt, J.; Thomas, A. Chem. Eur. J. 2016, 22, 7179. doi: 10.1002/chem.201600783
34. [34]
  Yan, Z. J.; Ren, H.; Ma, H. P.; Yuan, R. R.; Yuan, Y.; Zou, X. Q.; Sun, F. X.; Zhu, G. S. Microporous Mesoporous Mater. 2013, 173, 92. doi: 10.1016/j.micromeso.2013.02.006
35. [35]
  Chen, Q.; Wang, J. X.; Wang, Q.; Bian, N.; Li, Z. H.; Yan, C. G.; Han, B. H. Macromolecules 2011, 44, 7987. doi: 10.1021/ma201626s
36. [36]
  Ma, Q. Y.; Yang, B. X.; Li, J. Q. RSC Adv. 2015, 5, 64163. doi: 10.1039/C5RA11359H
37. [37]
  Qiao, S. L.; Du, Z. K.; Yang, C. P.; Zhou, Y. H.; Zhu, D. Q.; Wang, J. X.; Chen, X. H.; Yang, R. Q. Polymer 2014, 55, 1177. doi: 10.1016/j.polymer.2014.01.029
38. [38]
  Qiao, S. L.; Huang, W.; Du, Z. K.; Chen, X. H.; Shieh, F. K.; Yang, R. Q. New J. Chem. 2014, 39, 136.
39. [39]
  Ma, B. C.; Ghasimi, S.; Landfester, K.; Vilela, F.; Zhang, K. A. I. J. Mater. Chem. A 2015, 3, 16064. doi: 10.1039/C5TA03820K
40. [40]
  Zhang, T. T.; Wang, H. T.; Ma, H. P.; Sun, F. X.; Cui, X. Q.; Zhu, G. S. Acta Chim. Sinica 2013, 71, 1598. doi: 10.7503/cjcu20130173
41. [41]
  Zhang, H. J.; Zhang, C.; Wang, X. C.; Qiu, Z. X.; Liang, X. M.; Chen, B.; Xu, J. W.; Jiang, J. X.; Li, Y. D.; Li, H.; Wang, F. RSC Adv. 2016, 6, 113826. doi: 10.1039/C6RA20765K
42. [42]
  Lu, W. G.; Yuan, D. Q.; Zhao, D.; Schilling, C. I.; Plietzsch, O.; Muller, T.; Brase, S.; Guenther, J.; Blumel, J.; Krishna, R.; Li, Z.; Zhou, H. C. Chem. Mater. 2010, 22, 5964. doi: 10.1021/cm1021068
43. [43]
  Lu, W. G.; Wei, Z. W.; Yuan, D. Q.; Tian, J.; Fordham, S.; Zhou, H. C. Chem. Mater. 2014, 26, 4589. doi: 10.1021/cm501922h
44. [44]
  Wu, K. Y.; Guo, J.; Wang, C. C. Chem. Commun. 2014, 50, 695. doi: 10.1039/C3CC47234E
45. [45]
  Cao, Q.; Chen, Q.; Han, B. H. Acta Chim. Sinica 2015, 73, 541.
46. [46]
  Zhang, Y. H.; Li, Y. D.; Wang, F.; Zhao, Y.; Zhang, C.; Wang, X. Y.; Jiang, J. X. Polymer 2014, 55, 5746. doi: 10.1016/j.polymer.2014.09.014
47. [47]
  Zhang, C.; Kong, R.; Wang, X.; Xu, Y. F.; Wang, F.; Ren, W. F.; Wang, Y. H.; Su, F. B.; Jiang, J. X. Carbon 2017, 114, 608. doi: 10.1016/j.carbon.2016.12.064
48. [48]
  Zhao, Y.; Wang, X. Y.; Zhang, C.; Jiang, J. X. Acta Chim. Sinica 2015, 73, 634.
49. [49]
  Zhang, X.; Lu, J. Z.; Zhang, J. Chem. Mater. 2014, 26, 4023. doi: 10.1021/cm501717c
50. [50]
  Dawson, R.; Cooper, A. I.; Adams, D. J. Polym. Int. 2013, 62, 345.
51. [51]
  Yao, S. W.; Yang, X.; Yu, M.; Zhang, Y. H.; Jiang, J. X. J. Mater. Chem. A 2014, 2, 8054. doi: 10.1039/c4ta00375f
52. [52]
  Patel, H. A.; Je, S. H.; Park, J.; Jung, Y.; Coskun, A.; Yavuz, C. T. Chem. Eur. J. 2014, 20, 772. doi: 10.1002/chem.v20.3
53. [53]
  Mohanty, P.; Kull, L. D.; Landskron, K. Nat. Commun. 2011, 2, 401. doi: 10.1038/ncomms1405
1. [1]
  Bao Jia , Yunzhe Ke , Shiyue Sun , Dongxue Yu , Ying Liu , Shuaishuai Ding . Innovative Experimental Teaching for the Preparation and Modification of Conductive Organic Polymer Thin Films in Undergraduate Courses. University Chemistry, 2024, 39(10): 271-282. doi: 10.12461/PKU.DXHX202404121
2. [2]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
3. [3]
  Zongfei YANG , Xiaosen ZHAO , Jing LI , Wenchang ZHUANG . Research advances in heteropolyoxoniobates. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 465-480. doi: 10.11862/CJIC.20230306
4. [4]
  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
5. [5]
  Yan LIU , Jiaxin GUO , Song YANG , Shixian XU , Yanyan YANG , Zhongliang YU , Xiaogang HAO . Exclusionary recovery of phosphate anions with low concentration from wastewater using a CoNi-layered double hydroxide/graphene electronically controlled separation film. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1775-1783. doi: 10.11862/CJIC.20240043
6. [6]
  Fang Niu , Rong Li , Qiaolan Zhang . Analysis of Gas-Solid Adsorption Behavior in Resistive Gas Sensing Process. University Chemistry, 2024, 39(8): 142-148. doi: 10.3866/PKU.DXHX202311102
7. [7]
  Hong Zheng , Xin Peng , Chunwang Yi . The Tale of Caprolactam Cyclic Oligomers: The Ever-changing Life of “Princess Cyclo”. University Chemistry, 2024, 39(9): 40-47. doi: 10.12461/PKU.DXHX202403058
8. [8]
  Jiaxin Su , Jiaqi Zhang , Shuming Chai , Yankun Wang , Sibo Wang , Yuanxing Fang . Optimizing Poly(heptazine imide) Photoanodes Using Binary Molten Salt Synthesis for Water Oxidation Reaction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408012-. doi: 10.3866/PKU.WHXB202408012
9. [9]
  Ping ZHANG , Chenchen ZHAO , Xiaoyun CUI , Bing XIE , Yihan LIU , Haiyu LIN , Jiale ZHANG , Yu'nan CHEN . Preparation and adsorption-photocatalytic performance of ZnAl@layered double oxides. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1965-1974. doi: 10.11862/CJIC.20240014
10. [10]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
11. [11]
  Shicheng Yan . Experimental Teaching Design for the Integration of Scientific Research and Teaching: A Case Study on Organic Electrooxidation. University Chemistry, 2024, 39(11): 350-358. doi: 10.12461/PKU.DXHX202408036
12. [12]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
13. [13]
  Shasha Ma , Zujin Yang , Jianyong Zhang . Facile Synthesis of FeBTC Metal-Organic Gel and Its Adsorption of Cr₂O₇²⁻: A Physical Chemistry Innovation Experiment. University Chemistry, 2024, 39(8): 314-323. doi: 10.3866/PKU.DXHX202401008
14. [14]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . 钛酸铋/氮化碳无机有机复合S型异质结纯水光催化产过氧化氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-. doi: 10.3866/PKU.WHXB202403009
15. [15]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
16. [16]
  Changjun You , Chunchun Wang , Mingjie Cai , Yanping Liu , Baikang Zhu , Shijie Li . 引入内建电场强化BiOBr/C₃N₅ S型异质结中光载流子分离以实现高效催化降解微污染物. Acta Physico-Chimica Sinica, 2024, 40(11): 2407014-. doi: 10.3866/PKU.WHXB202407014
17. [17]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
18. [18]
  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
19. [19]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
20. [20]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(655)
HTML views(72)

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