Citation: Wei Zhao, Jia Qiao, Tian-Li Ning, Xi-Kui Liu. Scalable Ambient Pressure Synthesis of Covalent Organic Frameworks and Their Colorimetric Nanocomposites through Dynamic Imine Exchange Reactions[J]. Chinese Journal of Polymer Science, ;2018, 36(1): 1-7. doi: 10.1007/s10118-018-2010-5 shu

Scalable Ambient Pressure Synthesis of Covalent Organic Frameworks and Their Colorimetric Nanocomposites through Dynamic Imine Exchange Reactions

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

Corresponding author: Xi-Kui Liu, xkliu@scu.edu.cn
Received Date: 11 June 2017
Revised Date: 18 July 2017
Accepted Date: 18 July 2017
Available Online: 8 November 2017

A novel scale-up ambient pressure synthetic strategy for the preparation of imine-based covalent organic frameworks (COFs) was proposed through dynamic imine exchange reaction mechanism. The obtained COFs exhibited good crystallinity and much higher porosity comparable to their solvothermally synthesized counterparts. Moreover, under ambient pressure, the COF nanofibers could readily grow on the surface of polyimide films, and the resulted nanocomposite film showed an interesting colorimetric acid-responsive behavior.
- Covalent organic frameworks (COFs),
- Dynamic imine exchange,
- Ambient pressure synthesis
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[J]. Science, 2005,310:1166-1170. doi: 10.1126/science.1120411
2. [2]
  Ding S. Y., Wang W.. Covalent organic frameworks[J]. Chem. Soc. Rev., 2013,42:548-568. doi: 10.1039/C2CS35072F
3. [3]
  Waller P. J., Gándara F., Yaghi O. M.. Chemistry of covalent organic frameworks[J]. Acc. Chem. Res., 2015,48:3053-3063. doi: 10.1021/acs.accounts.5b00369
4. [4]
  Li Z. J., Ding S. Y., Xue H. D., Cao W., Wang W.. Synthesis of-C=N-linked covalent organic frameworks via the direct condensation of acetals and amines[J]. Chem. Commun., 2016,52:7217-7220. doi: 10.1039/C6CC00947F
5. [5]
  Colson J. W., Dichtel W. R.. Rationally synthesized two-dimensional polymers[J]. Nat. Chem., 2013,5:453-465. doi: 10.1038/nchem.1628
6. [6]
  Xiao F., Ding X. S., Jiang D. L.. Covalent organic frameworks[J]. Chem. Soc. Rev., 2012,41:6010-6022. doi: 10.1039/c2cs35157a
7. [7]
  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]. J. Am. Chem. Soc., 2011,133:19816-19822. doi: 10.1021/ja206846p
8. [8]
  Doonan C. J., Tranchemontagne D. J., Glover T. G., Hunt J. R., Yaghi O. M.. Exceptional ammonia uptake by a covalent organic framework[J]. Nat. Chem., 2010,2:235-238. doi: 10.1038/nchem.548
9. [9]
  Uribe-Romo F. J., Hunt J. R., Furukawa H., Klöck C., O'Keeffe M., Yaghi O. M.. A crystalline imine-linked 3-D porous covalent organic framework[J]. J. Am. Chem. Soc., 2009,131:4570-4571. doi: 10.1021/ja8096256
10. [10]
  Spitler E. L., Giovino M. R., White S. L., Dichtel W. R.. A mechanistic study of Lewis acid-catalyzed covalent organic framework formation[J]. Chem. Sci., 2011,2:1588-1953. doi: 10.1039/C1SC00260K
11. [11]
  Tan J., Namuangruk S., Kong W. F., Kungwan N., Guo J., Wang C. C.. Manipulation of amorphous-to-crystalline transformation:towards the construction of covalent organic framework hybrid microspheres with NIR photothermal conversion ability[J]. Angew. Chem. Int. Ed., 2016,55:13979-13984. doi: 10.1002/anie.v55.45
12. [12]
  Kuhn P., Antonietti M., Thomas A.. Porous, covalent triazine-based frameworks prepared by ionothermal synthesis[J]. Angew. Chem. Int. Ed., 2008,47:3450-3453. doi: 10.1002/(ISSN)1521-3773
13. [13]
  Furukawa H., Yaghi O. M.. Storage of hydrogen, methane, and carbon dioxide in highly porous covalent organic frameworks for clean energy applications[J]. J. Am. Chem. Soc., 2009,131:8875-8883. doi: 10.1021/ja9015765
14. [14]
  Wei H., Chai S. Z., Hu N. T., Yang Z., Wei L. M., Wang L.. The microwave-assisted solvothermal synthesis of a crystalline two-dimensional covalent organic framework with high CO₂ capacity[J]. Chem. Commun., 2015,51:12178-12181. doi: 10.1039/C5CC04680G
15. [15]
  Yang S., Kim J., Cho H., Kim S., Ahn W.. Facile synthesis of covalent organic frameworks COF-1 and COF-5 by sonochemical method[J]. RSC Adv., 2012,2:10179-10181. doi: 10.1039/c2ra21531d
16. [16]
  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]. J. Am. Chem. Soc., 2013,135:17853-17861. doi: 10.1021/ja408121p
17. [17]
  Biswal B. P., Chandra S., Kandambeth S., Lukose B., Heine T.. Mechanochemical synthesis of chemically stable isoreticular covalent organic frameworks[J]. J. Am. Chem. Soc., 2013,135:5328-5331. doi: 10.1021/ja4017842
18. [18]
  Jiang Y., Huang W., Wang J. Y., Wu Q., Wang H. J., Pan L. L., Liu X. K.. Green, scalable and morphology controlled synthesis of nanofibrous covalent organic frameworks and their nanohybrids through a vapor-assisted solid-state approach[J]. J. Mater. Chem. A, 2014,2:8201-8204. doi: 10.1039/c4ta00555d
19. [19]
  Segura J. L., Mancheno M. J., Zamora F.. Covalent organic frameworks based on Schiff-base chemistry:synthesis, properties and potential applications[J]. Chem. Soc. Rev., 2016,45:5635-5671. doi: 10.1039/C5CS00878F
20. [20]
  Kandambeth S., Shinde D. B., Panda M. K., Lukose B., Heine T., Banerjee R.. Enhancement of chemical stability and crystallinity in porphyrin-containing covalent organic frameworks by intramolecular hydrogen bonds[J]. Angew. Chem. Int. Ed., 2013,52:13052-13056. doi: 10.1002/anie.201306775
21. [21]
  Kandambeth S., Venkatesh V., Shinde D. B., Kumari S., Halder A.. Self-templated chemically stable hollow spherical covalent organic framework[J]. Nat. Commun., 20156. doi: 10.1038/ncomms7786
22. [22]
  Yan Y. Z., Chen L., Dai H. J., Chen Z. H., Li X., Liu X. K.. Morphosynthesis of nanostructured polyazomethines and carbon through constitutional dynamic chemistry controlled reaction induced crystallization process[J]. Polymer, 2012,53:1611-1616. doi: 10.1016/j.polymer.2012.02.025
23. [23]
  Chen L., Chen Z. H., Li X., Huang W., Li X. J., Liu X. K.. Dynamic imine chemistry assisted reaction induced hetero-epitaxial crystallization:novel approach towards aromatic polymer/CNT nanohybrid shish-kebabs and related hybrid crystalline structures[J]. Polymer, 2013,54:1739-1745. doi: 10.1016/j.polymer.2013.01.046
24. [24]
  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[J]. ACS Appl. Mater. Interfaces, 2013,5:8845-8849. doi: 10.1021/am402649g
25. [25]
  Brucks S. D., Bunck D. N., Dichtel W. R.. Functionalization of 3D covalent organic frameworks using monofunctional boronic acids[J]. Polymer, 2014,55:330-334. doi: 10.1016/j.polymer.2013.07.030
26. [26]
  Bunck D. N., Dichtel W. R.. Internal functionalization of three-dimensional covalent organic frameworks[J]. Angew. Chem. Int. Ed., 2012,51:1885-1889. doi: 10.1002/anie.v51.8
27. [27]
  Bunck D. N., Dichtel W. R.. Postsynthetic functionalization of 3D covalent organic frameworks[J]. Chem. Commun., 2013,49:2457-2459. doi: 10.1039/c3cc40358k
28. [28]
  Biswal B. P., Chandra S., Kandambeth S., Lukose B., Heine T.. Mechanochemical synthesis of chemically stable isoreticular covalent organic frameworks[J]. J. Am. Chem. Soc., 2013,135:5328-5331. doi: 10.1021/ja4017842
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