Citation: Wei Zhao, Tian-Pin Wang, Jia-Li Wu, Ru-Ping Pan, Xiang-Yang Liu, Xi-Kui Liu. Monolithic Covalent Organic Framework Aerogels through Framework Crystallization Induced Self-assembly: Heading towards Framework Materials Synthesis over All Length Scales[J]. Chinese Journal of Polymer Science, ;2019, 37(11): 1045-1052. doi: 10.1007/s10118-019-2313-1 shu

Monolithic Covalent Organic Framework Aerogels through Framework Crystallization Induced Self-assembly: Heading towards Framework Materials Synthesis over All Length Scales

College of Polymer Science and Engineering, Sichuan University, Chengdu 610065, China

Corresponding author: Xi-Kui Liu, xkliu@scu.edu.cn
Received Date: 15 April 2019
Revised Date: 30 May 2019
Available Online: 12 September 2019

Here, through the synergism between kinetic dynamic imine-exchange control and thermodynamic control, rarely observed compressible, porous, crystalline covalent organic framework (COF) aerogels were synthesized, the mechanism behind which is a framework crystallization induced self-assembly (FCISA) process. The prepared COF aerogel possessed extremely high BET surface over 2000 m²·g⁻¹ and high maximum equilibrium adsorption capacity toward bisphenol-A of 699 mg·g⁻¹ in aqueous solution.
- Covalent organic framework (COF),
- Aerogel,
- Framework crystallization
1. [1]
  Côté, A. P.; Benin, A. I.; Ockwig, N. W.; O'Keeffe, M.; Matzger, A. J.; Yaghi, O. M. Porous, crystalline, covalent organic frameworks. Science 2005, 310, 1166-1170. doi: 10.1126/science.1120411
2. [2]
  Oh, H.; Kalidindi, S. B.; Um, Y.; Bureekaew, S.; Schmid, R. A cryogenically flexible covalent organic framework for efficient hydrogen isotope separation by quantum sieving. Angew. Chem. Int. Ed. 2013, 52, 13219-13222. doi: 10.1002/anie.201307443
3. [3]
  Ding, S. Y.; Wang, W. Covalent organic frameworks (COFs): From design to applications. Chem. Soc. Rev., 2013, 42, 548-568 doi: 10.1039/C2CS35072F
4. [4]
  Qian, H. L.; Yang, C. X.; Yan, X. P. Bottom-up synthesis of chiral covalent organic frameworks and their bound capillaries for chiral separation. Nat. Commun. 2016, 7, 12104-12111. doi: 10.1038/ncomms12104
5. [5]
  Xu, H.; Chen, X.; Gao, J.; Lin, J. B.; Addicoat, M.; Irle, S.; Jiang, D. L. Catalytic covalent organic frameworks via pore surface engineering. Chem. Commun. 2014, 50, 1292-1294. doi: 10.1039/C3CC48813F
6. [6]
  Furukawa, H.; Yaghi, O. M. Storage of hydrogen, methane, and carbon dioxide in highly porous covalent organic frameworks for clean energy applications. J. Am. Chem. Soc. 2009, 131, 8875-8883. doi: 10.1021/ja9015765
7. [7]
  Deblase, C. R.; Silberstein, K. E.; Truong, T. T.; A, H. A.; Dichtel, W. R. Β. β-Ketoenamine-linked covalent organic frameworks capable of pseudocapacitive energy storage. J. Am. Chem. Soc. 2013, 135, 16821-16824. doi: 10.1021/ja409421d
8. [8]
  Peng, Y.; Zhao, M.; Chen, B.; Zhang, Z.; Huang, Y.; Dai, F.; Lai, Z.; Cui, X.; Tan, C.; Zhang, H. Hybridization of MOFs and COFs: A new strategy for construction of MOF@COF core-shell hybrid materials. Adv. Mater. 2018, 30, 1705454 doi: 10.1002/adma.v30.3
9. [9]
  Gole, B.; Stepanenko, V.; Rager, S.; Grgne, M.; Medina, D. D.; Bein, T.; Wgrthner, F.; Beuerle, F. Microtubular self‐assembly of covalent organic frameworks. Angew. Chem. Int. Ed. 2018, 57, 846 –850 doi: 10.1002/anie.201708526
10. [10]
  Halder, A.; Kandambeth, S.; Biswal, B. P.; Kaur, G.; Roy, N. C.; Addicoat, M.; Salunke, J. K.; Banerjee, S.; Vanka, K.; Heine, T.; Verma, S.; Banerjee, R. Decoding the morphological diversity in two dimensional crystalline porous polymers by core planarity modulation. Angew. Chem. Int. Ed. 2016, 55, 7806 –7810. doi: 10.1002/anie.201600087
11. [11]
  Kandambeth, S.; Venkatesh, V.; Shinde, D. B.; Kumari, S.; Halder, A.; Verma, S.; Banerjee, R. Self-templated chemically stable hollow spherical covalent organic framework. Nat. Comm. 2015, DOI: 10.1038/ncomms7786 doi: 10.1038/ncomms7786
12. [12]
  Tan, J.; Namuangruk, S.; Kong, W.; Kungwan, N.; Guo, J.; Wang, C. Manipulation of amorphous‐to‐crystalline transformation: Towards the construction of covalent organic framework hybrid microspheres with NIR photothermal conversion ability. Angew. Chem. Int. Ed. 2016, 55, 13979 –13984 doi: 10.1002/anie.v55.45
13. [13]
  Sun, B.; Liu, J.; Cao, A.; Song, W.; Wang, D. Interfacial synthesis of ordered and stable covalent organic frameworks on amino-functionalized carbon nanotubes with enhanced electrochemical performance. Chem. Commun., 2017, 53, 6303--6306 doi: 10.1039/C7CC01902E
14. [14]
  Ma, T.; Kapustin, E. A.; Yin, S.; Liang, L.; Zhou. Z.; Niu, J.; Li, L.; Wang, Y.; Su, J.; Li, J.; Wang, X.; Wang, W.; Wang, W.; Sun, J.; Yaghi, O. M. Single-crystal X-ray diffraction structures of covalent organic frameworks. Science, 2018, 361, 48–52 doi: 10.1126/science.aat7679
15. [15]
  Evans, A. M.; Parent, L. R.; Flanders, N. C.; Bisbey, R. P.; Vitaku, E.; Kirschner, M. S; Schaller, R. D.; Chen, L. X.; Gianneschi, N. C.; Dichtel, W. R. Seeded growth of single-crystal two-dimensional covalent organic frameworks. Science, 2018, 361, 52–57 doi: 10.1126/science.aar7883
16. [16]
  Dogru, M.; Handloser, M.; Auras, F.; Kunz, T.; Medina, D. A. A photoconductive thienothiophene‐based covalent organic framework showing charge transfer towards included fullerene. Angew. Chem. Int. Ed. 2013, 125, 2992-2996. doi: 10.1002/ange.201208514
17. [17]
  Feng, X.; Chen, L.; Honsho, Y.; Saengsawang, O.; Liu, L. L.; Wang, L.; Saeki, A.; Irle, S.; Seki, S.; Dong, Y. P.; Jiang, D. L. An ambipolar conducting covalent organic framework with self‐sorted and periodic electron donor‐acceptor ordering. Adv. Mater. 2012, 24, 3026-3031. doi: 10.1002/adma.v24.22
18. [18]
  Ding, S. Y.; Gao, J.; Wang, Q.; Zhang, Y.; Song, W. G.; Su, C. Y.; Wang, W. Construction of covalent organic framework for catalysis: Pd/COF-LZU1 in Suzuki-Miyaura coupling reaction. J. Am. Chem. Soc. 2011, 133, 19816-19822. doi: 10.1021/ja206846p
19. [19]
  Calik, M.; Auras, F.; Salonen, L. M.; Bader, K.; Grill, I.; Handloser, M.; Medina, D. D.; Dogru, M.; Löbermann, F.; Trauner, D.; Hartschuh, A.; Bein, T. Extraction of photogenerated electrons and holes from a covalent organic framework integrated heterojunction. J. Am. Chem. Soc. 2014, 136, 17802-17807. doi: 10.1021/ja509551m
20. [20]
  Warren, N. J.; Armes, S. P. Polymerization-induced self-assembly of block copolymer nano-objects via RAFT aqueous dispersion polymerization. J. Am. Chem. Soc. 2014, 136, 10174−10185 doi: 10.1021/ja502843f
21. [21]
  Smith, B. J.; Hwang, N.; Chavez, A. D.; Novotney, J. L.; Dichtel, W. R. Growth rates and water stability of 2D boronate ester covalent organic frameworks. Chem. Commun. 2015, 51, 7532-7535. doi: 10.1039/C5CC00379B
22. [22]
  Smith, B. J.; Overholts, A. C.; Hwang, N.; Dichtel, W. R. Insight into the crystallization of amorphous imine-linked polymer networks to 2D covalent organic frameworks. Chem. Commun. 2016, 52, 3690-3693. doi: 10.1039/C5CC10221A
23. [23]
  Smith, B. J.; Dichtel, W. R. Mechanistic studies of two-dimensional covalent organic frameworks rapidly polymerized from initially homogenous conditions. J. Am. Chem. Soc. 2014, 136, 8783-8789. doi: 10.1021/ja5037868
24. [24]
  Bunck, D. N.; Dichtel, W. R. Internal functionalization of three‐dimensional covalent organic frameworks. Angew. Chem. Int. Ed. 2012, 51, 1885-1889. doi: 10.1002/anie.v51.8
25. [25]
  Vitaku, E.; Dichtel, W. R. Synthesis of 2D imine-linked covalent organic frameworks through formal transimination reactions. J. Am. Chem. Soc. 2017, 139, 12911−12914. doi: 10.1021/jacs.7b06913
26. [26]
  Biswal, B. P.; Chandra, S.; Kandambeth, S.; Lukose, B.; Heine, T.; Banerjee, R. Mechanochemical synthesis of chemically stable isoreticular covalent organic frameworks. J. Am. Chem. Soc. 2013, 135, 5328-5331. doi: 10.1021/ja4017842
27. [27]
  Huang, W.; Jiang, Y.; Li, X.; Li, X. J.; Wang, J. Y.; Wu, Q.; Liu, X. K. Solvothermal synthesis of microporous, crystalline covalent organic framework nanofibers and their colorimetric nanohybrid structures. ACS Appl. Mater. Inter. 2013, 5, 8845-8849. doi: 10.1021/am402649g
28. [28]
  Xu, H.; Tao, S. S.; Jiang, D. L. Proton conduction in crystalline and porous covalent organic frameworks. Nat. Mater. 2016, 15, 722-726. doi: 10.1038/nmat4611
29. [29]
  Kandambeth, S.; Mallick, A.; Lukose, B.; Mane, M. V.; Heine, T.; Banerjee, R. Construction of crystalline 2D covalent organic frameworks with remarkable chemical (acid/base) stability via a combined reversible and irreversible route. J. Am. Chem. Soc. 2012, 134, 19524-19527. doi: 10.1021/ja308278w
30. [30]
  Kuecken, S.; Schmidt, J.; Zhi, L.; Thomas, A. Conversion of amorphous polymer networks to covalent organic frameworks under ionothermal conditions: A facile synthesis route for covalent triazine frameworks. J. Mater. Chem. A 2015, 3, 24422-24427. doi: 10.1039/C5TA07408H
31. [31]
  Gao, Q.; Bai, L.; Zeng, Y.; Wang, P.; Zhang, X.; Zou, R.; Zhao, Y. Reconstruction of covalent organic frameworks by dynamic equilibrium. Chemistry 2015, 21, 16818-16822. doi: 10.1002/chem.v21.47
32. [32]
  Iwasawa, N.; Takahagi, H. Boronic esters as a system for crystallization-induced dynamic self-assembly equipped with an " on-off” switch for equilibration. J. Am. Chem. Soc. 2007, 129, 7754-7755. doi: 10.1021/ja072319q
33. [33]
  Gilroy, J. B.; Gädt, T.; Whittell, G. R.; Chabanne, L.; Mitchels, J. M.; Richardson, R. M.; Winnik, M. A.; Manners, I. Monodisperse cylindrical micelles by crystallization-driven living self-assembly. Nat. Chem. 2010, 2, 566-570. doi: 10.1038/nchem.664
34. [34]
  Chandra, S.; Kandambeth, S.; Biswal, B. P.; Lukose, B.; Kunjir, S. M.; Chaudhary, M.; Babarao, R.; Heine, T.; Banerjee, R. Chemically stable multilayered covalent organic nanosheets from covalent organic frameworks via mechanical delamination. J. Am. Chem. Soc. 2013, 135, 17853-17861. doi: 10.1021/ja408121p
1. [1]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
2. [2]
  Yinyin Xu , Yuanyuan Li , Jingbo Feng , Chen Wang , Yan Zhang , Yukun Wang , Xiuwen Cheng . Covalent organic frameworks doped with manganese-metal organic framework for peroxymonosulfate activation. Chinese Chemical Letters, 2024, 35(4): 108838-. doi: 10.1016/j.cclet.2023.108838
3. [3]
  Guorong Li , Yijing Wu , Chao Zhong , Yixin Yang , Zian Lin . Predesigned covalent organic framework with sulfur coordination: Anchoring Au nanoparticles for sensitive colorimetric detection of Hg(Ⅱ). Chinese Chemical Letters, 2024, 35(5): 108904-. doi: 10.1016/j.cclet.2023.108904
4. [4]
  Yue Qian , Zhoujia Liu , Haixin Song , Ruize Yin , Hanni Yang , Siyang Li , Weiwei Xiong , Saisai Yuan , Junhao Zhang , Huan Pang . Imide-based covalent organic framework with excellent cyclability as an anode material for lithium-ion battery. Chinese Chemical Letters, 2024, 35(6): 108785-. doi: 10.1016/j.cclet.2023.108785
5. [5]
  Yuting Wu , Haifeng Lv , Xiaojun Wu . Design of two-dimensional porous covalent organic framework semiconductors for visible-light-driven overall water splitting: A theoretical perspective. Chinese Journal of Structural Chemistry, 2024, 43(11): 100375-100375. doi: 10.1016/j.cjsc.2024.100375
6. [6]
  Jingyu Cai , Xiaoyu Miao , Yulai Zhao , Longqiang Xiao . Exploratory Teaching Experiment Design of FeOOH-RGO Aerogel for Photocatalytic Benzene to Phenol. University Chemistry, 2024, 39(4): 169-177. doi: 10.3866/PKU.DXHX202311028
7. [7]
  Feng Zheng , Ruxun Yuan , Xiaogang Wang . “Research-Oriented” Comprehensive Experimental Design in Polymer Chemistry: the Case of Polyimide Aerogels. University Chemistry, 2024, 39(10): 210-218. doi: 10.12461/PKU.DXHX202404027
8. [8]
  Ziyi Zhu , Yang Cao , Jun Zhang . CO2-switched porous metal-organic framework magnets. Chinese Journal of Structural Chemistry, 2024, 43(2): 100241-100241. doi: 10.1016/j.cjsc.2024.100241
9. [9]
  Liangji Chen , Zhen Yuan , Fudong Feng , Xin Zhou , Zhile Xiong , Wuji Wei , Hao Zhang , Banglin Chen , Shengchang Xiang , Zhangjing Zhang . A hydrogen-bonded organic framework containing fluorescent carbazole and responsive pyridyl units for sensing organic acids. Chinese Chemical Letters, 2024, 35(9): 109344-. doi: 10.1016/j.cclet.2023.109344
10. [10]
  Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
11. [11]
  Feifei Wang , Hang Yao , Xinyue Wu , Yijian Tang , Yang Bai , Hui Chong , Huan Pang . Metal–organic framework and its composites modulate macrophage polarization in the treatment of inflammatory diseases. Chinese Chemical Letters, 2024, 35(5): 108821-. doi: 10.1016/j.cclet.2023.108821
12. [12]
  Tengjia Ni , Xianbiao Hou , Huanlei Wang , Lei Chu , Shuixing Dai , Minghua Huang . Controllable defect engineering based on cobalt metal-organic framework for boosting oxygen evolution reaction. Chinese Journal of Structural Chemistry, 2024, 43(1): 100210-100210. doi: 10.1016/j.cjsc.2023.100210
13. [13]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
14. [14]
  Ying Li , Yanjun Xu , Xingqi Han , Di Han , Xuesong Wu , Xinlong Wang , Zhongmin Su . A new metal–organic rotaxane framework for enhanced ion conductivity of solid-state electrolyte in lithium-metal batteries. Chinese Chemical Letters, 2024, 35(9): 109189-. doi: 10.1016/j.cclet.2023.109189
15. [15]
  Xiangshuai Li , Jian Zhao , Li Luo , Zhuohao Jiao , Ying Shi , Shengli Hou , Bin Zhao . Visual and portable detection of metronidazole realized by metal-organic framework flexible sensor and smartphone scanning. Chinese Chemical Letters, 2024, 35(10): 109407-. doi: 10.1016/j.cclet.2023.109407
16. [16]
  Jing Wang , Zhongliao Wang , Jinfeng Zhang , Kai Dai . Single-layer crystalline triazine-based organic framework photocatalysts with different linking groups for H2O2 production. Chinese Journal of Structural Chemistry, 2023, 42(12): 100202-100202. doi: 10.1016/j.cjsc.2023.100202
17. [17]
  Yuxin Wang , Zhengxuan Song , Yutao Liu , Yang Chen , Jinping Li , Libo Li , Jia Yao . Methyl functionalization of trimesic acid in copper-based metal-organic framework for ammonia colorimetric sensing at high relative humidity. Chinese Chemical Letters, 2024, 35(6): 108779-. doi: 10.1016/j.cclet.2023.108779
18. [18]
  Xuying Yu , Jiarong Mi , Yulan Han , Cai Sun , Mingsheng Wang , Guocong Guo . A stable radiochromic semiconductive viologen-based metal–organic framework for dual-mode direct X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109233-. doi: 10.1016/j.cclet.2023.109233
19. [19]
  Benjian Xin , Rui Wang , Lili Liu , Zhiqiang Niu . Metal-organic framework derived MnO@C/CNTs composite for high-rate lithium-based semi-solid flow batteries. Chinese Journal of Structural Chemistry, 2023, 42(11): 100116-100116. doi: 10.1016/j.cjsc.2023.100116
20. [20]
  Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(666)
HTML views(5)

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