Room Temperature Batch and Continuous Flow Synthesis of Water-Stable Covalent Organic Frameworks (COFs)

Chemistry of Materials

Volumn 28, Issue 14, 2016, Pages 5095-5101

  Peng, Yongwu ^a   Wong, Wai Kuan ^a   Hu, Zhigang ^a   Cheng, Youdong ^a   Yuan, Daqiang ^b   Khan, Saif A ^a   Zhao, Dan ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b FUJIAN INSTITUTE OF RESEARCH ON THE STRUCTURE OF MATTER   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ERROR CORRECTION; NITROGEN COMPOUNDS; POROUS MATERIALS;

AMBIENT CONDITIONS; CONTINUOUS PROCESS; CONTINUOUS-FLOW SYNTHESIS; COVALENT ORGANIC FRAMEWORKS; CRYSTALLIZATION PROCESS; LARGE-SCALE APPLICATIONS; SYNTHETIC CONDITIONS; TWO DIMENSIONAL (2 D);

MONOMERS;

EID: 84979902008     PISSN: 08974756     EISSN: 15205002     Source Type: Journal    
DOI: 10.1021/acs.chemmater.6b01954     Document Type: Article

References (55)

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 10.1126/science.1120411
2. El-Kaderi, H. M.; Hunt, J. R.; Mendoza-Cortés, J. L.; Côté, A. P.; Taylor, R. E.; O'Keeffe, M.; Yaghi, O. M. Designed synthesis of 3D covalent organic frameworks Science 2007, 316, 268-272 10.1126/science.1139915
3. Mastalerz, M. The next generation of shape-persistant zeolite analogues: covalent organic frameworks Angew. Chem., Int. Ed. 2008, 47, 445-447 10.1002/anie.200703871
4. Colson, J. W.; Dichtel, W. R. Rationally synthesized two-dimensional polymers Nat. Chem. 2013, 5, 453-465 10.1038/nchem.1628
5. Ascherl, L.; Sick, T.; Margraf, J. T.; Lapidus, S. H.; Calik, M.; Hettstedt, C.; Karaghiosoff, K.; Doeblinger, M.; Clark, T.; Chapman, K. W.; Auras, F.; Bein, T. Molecular docking sites designed for the generation of highly crystalline covalent organic frameworks Nat. Chem. 2016, 8, 310-316 10.1038/nchem.2444
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 10.1021/ja9015765
7. Dogru, M.; Handloser, M.; Auras, F.; Kunz, T.; Medina, D.; Hartschuh, A.; Knochel, P.; Bein, T. A photoconductive thienothiophene-based covalent organic framework showing charge transfer towards included fullerene Angew. Chem., Int. Ed. 2013, 52, 2920-2924 10.1002/anie.201208514
8. Dogru, M.; Bein, T. On the road towards electroactive covalent organic frameworks Chem. Commun. 2014, 50, 5531-5546 10.1039/C3CC46767H
9. Chen, L.; Furukawa, K.; Gao, J.; Nagai, A.; Nakamura, T.; Dong, Y. P.; Jiang, D. L. Photoelectric covalent organic frameworks: Converting open lattices into ordered donor-acceptor heterojunctions J. Am. Chem. Soc. 2014, 136, 9806-9809 10.1021/ja502692w
10. Cai, S. L.; Zhang, Y. B.; Pun, A. B.; He, B.; Yang, J. H.; Toma, F. M.; Sharp, I. D.; Yaghi, O. M.; Fan, J.; Zheng, S. R.; Zhang, W. G.; Liu, Y. Tunable electrical conductivity in oriented thin films of tetrathiafulvalene-based covalent organic framework Chem. Sci. 2014, 5, 4693-4700 10.1039/C4SC02593H
11. Duhović, S.; Dinca, M. Synthesis and electrical properties of covalent organic frameworks with heavy chalcogens Chem. Mater. 2015, 27, 5487-5490 10.1021/acs.chemmater.5b02358
12. Peng, Y. W.; Hu, Z. G.; Gao, Y. J.; Yuan, D. Q.; Kang, Z. X.; Qian, Y. H.; Yan, N.; Zhao, D. Synthesis of a sulfonated two-dimensional covalent organic framework as an efficient solid acid catalyst for biobased chemical conversion ChemSusChem 2015, 8, 3208-3212 10.1002/cssc.201500755
13. Vyas, V. S.; Haase, F.; Stegbauer, L.; Savasci, G.; Podjaski, F.; Ochsenfeld, C.; Lotsch, B. V. A tunable azine covalent organic framework platform for visible light-induced hydrogen generation Nat. Commun. 2015, 6, 8508 10.1038/ncomms9508
14. Xu, H.; Gao, J.; Jiang, D. L. Stable, crystalline, porous, covalent organic frameworks as a platform for chiral organocatalysts Nat. Chem. 2015, 7, 905-912 10.1038/nchem.2352
15. 2 reduction in water Science 2015, 349, 1208-1213 10.1126/science.aac8343
16. Feng, X.; Ding, X. S.; Jiang, D. L. Covalent organic frameworks Chem. Soc. Rev. 2012, 41, 6010-6022 10.1039/c2cs35157a
17. Ding, S. Y.; Wang, W. Covalent organic frameworks (COFs): from design to applications Chem. Soc. Rev. 2013, 42, 548-568 10.1039/C2CS35072F
18. Waller, P. J.; Gándara, F.; Yaghi, O. M. Chemistry of covalent organic frameworks Acc. Chem. Res. 2015, 48, 3053-3063 10.1021/acs.accounts.5b00369
19. 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 10.1021/ja5037868
20. Hunt, J. R.; Doonan, C. J.; LeVangie, J. D.; Côté, A. P.; Yaghi, O. M. Reticular synthesis of covalent organic borosilicate frameworks J. Am. Chem. Soc. 2008, 130, 11872-11873 10.1021/ja805064f
21. Campbell, N. L.; Clowes, R.; Ritchie, L. K.; Cooper, A. I. Rapid microwave synthesis and purification of porous covalent organic frameworks Chem. Mater. 2009, 21, 204-206 10.1021/cm802981m
22. 2 capacity Chem. Commun. 2015, 51, 12178-12181 10.1039/C5CC04680G
23. Kuhn, P.; Antonietti, M.; Thomas, A. Porous, covalent triazine-based frameworks prepared by ionothermal synthesis Angew. Chem., Int. Ed. 2008, 47, 3450-3453 10.1002/anie.200705710
24. Yang, S.-T.; Kim, J.; Cho, H.-Y.; Kim, S.; Ahn, W.-S. Facile synthesis of covalent organic frameworks COF-1 and COF-5 by sonochemical method RSC Adv. 2012, 2, 10179-10181 10.1039/c2ra21531d
25. Das, G.; Shinde, D. B.; Kandambeth, S.; Biswal, B. P.; Banerjee, R. Mechanosynthesis of imine, beta-ketoenamine, and hydrogen-bonded imine-linked covalent organic frameworks using liquid-assisted grinding Chem. Commun. 2014, 50, 12615-12618 10.1039/C4CC03389B
26. Jiang, Y.; Huang, W.; Wang, J.; Wu, Q.; Wang, H.; Pan, L.; Liu, X. Green, scalable and morphology controlled synthesis of nanofibrous covalent organic frameworks and their nanohybrids through a vapor-assisted solid-state approach J. Mater. Chem. A 2014, 2, 8201-8204 10.1039/c4ta00555d
27. Medina, D. D.; Rotter, J. M.; Hu, Y.; Dogru, M.; Werner, V.; Auras, F.; Markiewicz, J. T.; Knochel, P.; Bein, T. Room temperature synthesis of covalent-organic framework films through vapor-assisted conversion J. Am. Chem. Soc. 2015, 137, 1016-1019 10.1021/ja510895m
28. Gimeno-Fabra, M.; Munn, A. S.; Stevens, L. A.; Drage, T. C.; Grant, D. M.; Kashtiban, R. J.; Sloan, J.; Lester, E.; Walton, R. I. Instant MOFs: continuous synthesis of metal-organic frameworks by rapid solvent mixing Chem. Commun. 2012, 48, 10642-10644 10.1039/c2cc34493a
29. Faustini, M.; Kim, J.; Jeong, G. Y.; Kim, J. Y.; Moon, H. R.; Ahn, W. S.; Kim, D. P. Microfluidic approach toward continuous and ultrafast synthesis of metal-organic framework crystals and hetero structures in confined microdroplets J. Am. Chem. Soc. 2013, 135, 14619-14626 10.1021/ja4039642
30. Paseta, L.; Seoane, B.; Julve, D.; Sebastian, V.; Tellez, C.; Coronas, J. Accelerating the controlled synthesis of metal-organic frameworks by a microfluidic approach: a nanoliter continuous reactor ACS Appl. Mater. Interfaces 2013, 5, 9405-9410 10.1021/am4029872
31. Kim, K. J.; Li, Y. J.; Kreider, P. B.; Chang, C. H.; Wannenmacher, N.; Thallapally, P. K.; Ahn, H. G. High-rate synthesis of Cu-BTC metal-organic frameworks Chem. Commun. 2013, 49, 11518-11520 10.1039/c3cc46049e
32. Rubio-Martinez, M.; Batten, M. P.; Polyzos, A.; Carey, K. C.; Mardel, J. I.; Lim, K. S.; Hill, M. R. Versatile, high quality and scalable continuous flow production of metal-organic frameworks Sci. Rep. 2014, 4, 5443 10.1038/srep05443
33. Briggs, M. E.; Slater, A. G.; Lunt, N.; Jiang, S.; Little, M. A.; Greenaway, R. L.; Hasell, T.; Battilocchio, C.; Ley, S. V.; Cooper, A. I. Dynamic flow synthesis of porous organic cages Chem. Commun. 2015, 51, 17390-17393 10.1039/C5CC07447A
34. Chong, J. H.; Sauer, M.; Patrick, B. O.; MacLachlan, M. J. Highly stable keto-enamine salicylideneanilines Org. Lett. 2003, 5, 3823-3826 10.1021/ol0352714
35. Bunck, D. N.; Dichtel, W. R. Bulk synthesis of exfoliated two-dimensional polymers using hydrazone-linked covalent organic frameworks J. Am. Chem. Soc. 2013, 135, 14952-14955 10.1021/ja408243n
36. 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 10.1021/ja206846p
37. 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 10.1021/ja308278w
38. Dalapati, S.; Addicoat, M.; Jin, S.; Sakurai, T.; Gao, J.; Xu, H.; Irle, S.; Seki, S.; Jiang, D. Rational design of crystalline supermicroporous covalent organic frameworks with triangular topologies Nat. Commun. 2015, 6, 7786 10.1038/ncomms8786
39. DeBlase, C. R.; Silberstein, K. E.; Truong, T. T.; Abruña, H. D.; Dichtel, W. R. β-Ketoenamine-linked covalent organic frameworks capable of pseudocapacitive energy storage J. Am. Chem. Soc. 2013, 135, 16821-16824 10.1021/ja409421d
40. Sun, D. F.; Ke, Y. X.; Mattox, T. M.; Ooro, B. A.; Zhou, H. C. Temperature-dependent supramolecular stereoisomerism in porous copper coordination networks based on a designed carboxylate ligand Chem. Commun. 2005, 5447-5449 10.1039/b505664k
41. Ke, Y. X.; Collins, D. J.; Sun, D. F.; Zhou, H. C. (10,3)-a Noninterpenetrated network built from a piedfort ligand pair Inorg. Chem. 2006, 45, 1897-1899 10.1021/ic051900p
42. 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 10.1039/C5CC10221A
43. Ding, H.; Meng, X.; Cui, X.; Yang, Y.; Zhou, T.; Wang, C.; Zeller, M.; Wang, C. Highly-efficient synthesis of covalent porphyrinic cages via DABCO-templated imine condensation reactions Chem. Commun. 2014, 50, 11162-11164 10.1039/C4CC05449K
44. Ding, H.; Wu, X.; Zeller, M.; Xie, Y.; Wang, C. Controllable synthesis of covalent porphyrinic cages with varying sizes via template-directed imine condensation reactions J. Org. Chem. 2015, 80, 9360-9364 10.1021/acs.joc.5b01781
45. Tozawa, T.; Jones, J. T. A.; Swamy, S. I.; Jiang, S.; Adams, D. J.; Shakespeare, S.; Clowes, R.; Bradshaw, D.; Hasell, T.; Chong, S. Y.; Tang, C.; Thompson, S.; Parker, J.; Trewin, A.; Bacsa, J.; Slawin, A. M. Z.; Steiner, A.; Cooper, A. I. Porous organic cages Nat. Mater. 2009, 8, 973-978 10.1038/nmat2545
46. Zhang, G.; Mastalerz, M. Organic cage compounds-from shape-persistency to function Chem. Soc. Rev. 2014, 43, 1934-1947 10.1039/C3CS60358J
47. Li, Z. P.; Feng, X.; Zou, Y. C.; Zhang, Y. W.; Xia, H.; Liu, X. M.; Mu, Y. A 2D azine-linked covalent organic framework for gas storage applications Chem. Commun. 2014, 50, 13825-13828 10.1039/C4CC05665E
48. 2 separation Chem. Mater. 2016, 28, 1277-1285 10.1021/acs.chemmater.5b02902
49. 2 adsorption through ligand-directed catenation Inorg. Chem. 2008, 47, 11-13 10.1021/ic701917w
50. Uribe-Romo, F. J.; Doonan, C. J.; Furukawa, H.; Oisaki, K.; Yaghi, O. M. Crystalline covalent organic frameworks with hydrazone linkages J. Am. Chem. Soc. 2011, 133, 11478-11481 10.1021/ja204728y
51. Stegbauer, L.; Schwinghammer, K.; Lotsch, B. V. A hydrazone-based covalent organic framework for photocatalytic hydrogen production Chem. Sci. 2014, 5, 2789-2793 10.1039/C4SC00016A
52. Sun, D. F.; Ma, S. Q.; Ke, Y. X.; Petersen, T. M.; Zhou, H. C. Synthesis, characterization, and photoluminescence of isostructural Mn, Co, and Zn MOFs having a diamondoid structure with large tetrahedral cages and high thermal stability Chem. Commun. 2005, 2663-2665 10.1039/b502007g
53. Hartman, R. L.; McMullen, J. P.; Jensen, K. F. Deciding whether to go with the flow: evaluating the merits of flow reactors for synthesis Angew. Chem., Int. Ed. 2011, 50, 7502-7519 10.1002/anie.201004637
54. Myers, R. M.; Fitzpatrick, D. E.; Turner, R. M.; Ley, S. V. Flow chemistry meets advanced functional materials Chem.-Eur. J. 2014, 20, 12348-12366 10.1002/chem.201402801
55. Ley, S. V.; Fitzpatrick, D. E.; Myers, R. M.; Battilocchio, C.; Ingham, R. J. Machine-assisted organic synthesis Angew. Chem., Int. Ed. 2015, 54, 10122-10136 10.1002/anie.201501618