Stable, crystalline, porous, covalent organic frameworks as a platform for chiral organocatalysts

Nature Chemistry

Volumn 7, Issue 11, 2015, Pages 905-912

  Xu, Hong ^a   Gao, Jia ^a   Jiang, Donglin ^a  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84945119732     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.2352     Document Type: Article

References (42)

1. Feng, X., Ding, X. & Jiang, D. Covalent organic frameworks. Chem. Soc. Rev. 41, 6010-6022 (2012).
2. Ding, S. Y. & Wang, W. Covalent organic frameworks (COFs): from design to applications. Chem. Soc. Rev. 42, 548-568 (2013).
3. Cote, A. P. et al. Porous, crystalline, covalent organic frameworks. Science 310, 1166-1170 (2005).
4. Tilford, R.W., Gemmill, W. R., zur Loye, H. C. & Lavigne, J. J. Facile synthesis of a highly crystalline, covalently linked porous boronate network. Chem. Mater. 18, 5296-5301 (2006).
5. Belowich, M. E. & Stoddart, J. F. Dynamic imine chemistry. Chem. Soc. Rev. 41, 2003-2024 (2012).
6. Xiang, Z. H., Cao, D. P. & Dai, L. M. Well-defined two dimensional covalent organic polymers: rational design, controlled syntheses, and potential applications. Polym. Chem. 6, 1896-1911 (2015).
7. Cote, A. P., El-Kaderi, H. M., Furukawa, H., Hunt, J. R. & Yaghi, O. M. Reticular synthesis of microporous and mesoporous 2D covalent organic frameworks. J. Am. Chem. Soc. 129, 12914-12915 (2007).
8. Wan, S., Guo, J., Kim, J., Ihee, H. & Jiang, D. A belt-shaped, blue luminescent, and semiconducting covalent organic framework. Angew. Chem. Int. Ed. 47, 8826-8830 (2008).
9. Tilford, R. W., Mugavero, S. J., Pellechia, P. J. & Lavigne, J. J. Tailoring microporosity in covalent organic frameworks. Adv. Mater. 20, 2741-2746 (2008).
10. Wan, S., Guo, J., Kim, J., Ihee, H. & Jiang, D. A photoconductive covalent organic framework: self-condensed arene cubes composed of eclipsed 2D polypyrene sheets for photocurrent generation. Angew. Chem. Int. Ed. 48, 5439-5442 (2009).
11. Campbell, N. L., Clowes, R., Ritchie, L. K. & Cooper, A. I. Rapid microwave synthesis and purification of porous covalent organic frameworks. Chem. Mater. 21, 204-206 (2009).
12. Spitler, E. L. & Dichtel, W. R. Lewis acid-catalysed formation of two-dimensional phthalocyanine covalent organic frameworks. Nature Chem. 2, 672-677 (2010).
13. Wan, S. et al. Covalent organic frameworks with high charge carrier mobility. Chem. Mater. 23, 4094-4097 (2011).
14. 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. 133, 11478-11481 (2011).
15. Kandambeth, S. et al. Construction of crystalline 2D covalent organic frameworks with remarkable chemical (acid/base) stability via a combined reversible and irreversible route. J. Am. Chem. Soc. 134, 19524-19527 (2012).
16. Dalapati, S. et al. An azine-linked covalent organic framework. J. Am. Chem. Soc. 135, 17310-17313 (2013).
17. Kuhn, P., Antonietti, M. & Thomas, A. Porous, covalent triazine-based frameworks prepared by ionothermal synthesis. Angew. Chem. Int. Ed. 47, 3450-3453 (2008).
18. Guo, J. et al. Conjugated organic framework with three-dimensionally ordered stable structure and delocalized φ clouds. Nature Commun. 4, 2736 (2013).
19. Lukose, B., Kuc, A. & Heine, T. The structure of layered covalent-organic frameworks. Chem. Eur. J. 17, 2388-2392 (2011).
20. Nagai, A. et al. Pore surface engineering in covalent organic frameworks. Nature Commun. 2, 536 (2011).
21. Dogru, M., Sonnauer, A., Gavryushin, A., Knochel, P. & Bein, T. A covalent organic framework with 4 nm open pores. Chem. Commun. 47, 1707-1709 (2011).
22. Chen, X., Addicoat, M., Irle, S., Nagai, A. & Jiang, D. Control of crystallinity and porosity of covalent organic frameworks by managing interlayer interactions based on self-complementary φ-electronic force. J. Am. Chem. Soc. 135, 546-549 (2013).
23. Biswal, B. P. et al. Mechanochemical synthesis of chemically stable isoreticular covalent organic frameworks. J. Am. Chem. Soc. 135, 5328-5331 (2013).
24. Kandambeth, S. et al. Enhancement of chemical stability and crystallinity in porphyrin-containing covalent organic frameworks by intramolecular hydrogen bonds. Angew. Chem. Int. Ed. 52, 13052-13056 (2013).
25. Chandra, S. et al. Phosphoric acid loaded azo-based covalent organic framework for proton conduction. J. Am. Chem. Soc. 136, 6570-6573 (2014).
26. Du, Y. et al. Experimental and computational studies of pyridine-Assisted postsynthesis modified air stable covalent-organic frameworks. Chem. Commun. 48, 4606-4608 (2012).
27. Ding, S. Y. et al. Construction of covalent organic framework for catalysis: Pd/COF-LZU1 in Suzuki-Miyaura coupling reaction. J. Am. Chem. Soc. 133, 19816-19822 (2011).
28. Rabbani, M. G. et al. A 2D mesoporous imine-linked covalent organic framework for high pressure gas storage applications. Chem. Eur. J. 19, 3324-3328 (2013).
29. Xu, H. et al. Catalytic covalent organic frameworks via pore surface engineering. Chem. Commun. 50, 1292-1294 (2014).
30. MacMillan, D. W. The advent and development of organocatalysis. Nature 455, 304-308 (2008).
31. List, B. Proline-catalyzed asymmetric reactions. Tetrahedron 58, 5573-5590 (2002).
32. Benaglia, M., Puglisi, A. & Cozzi, F. Polymer-supported organic catalysts. Chem. Rev. 103, 3401-3429 (2003).
33. Lee, J. et al. Metal-organic framework materials as catalysts. Chem. Soc. Rev. 38, 1450-1459 (2009).
34. Yoon, M., Srirambalaji, R. & Kim, K. Homochiral metal-organic frameworks for asymmetric heterogeneous catalysis. Chem. Rev. 112, 1196-1231 (2012).
35. Banerjee, M. et al. Postsynthetic modification switches an achiral framework to catalytically active homochiral metal-organic porous materials. J. Am. Chem. Soc. 131, 7524-7525 (2009).
36. Dang, D., Wu, P., He, C., Xie, Z. & Duan, C.Homochiralmetal-organic frameworks for heterogeneous asymmetric catalysis. J. Am. Chem. Soc. 132, 14321-14323 (2010).
37. Lun, D. J., Waterhouse, G. I. & Telfer, S. G. A general thermolabile protecting group strategy for organocatalytic metal-organic frameworks. J. Am. Chem. Soc. 133, 5806-5809 (2011).
38. Notz, W., Tanaka, F. & Barbas, C. F. III. Enamine-based organocatalysis with proline and diamines: The development of direct catalytic asymmetric aldol, Mannich, Michael, and Diels-Alder reactions. Acc. Chem. Res. 37, 580-591 (2004).
39. Berner, O. M., Tedeschi, L. & Enders, D. Asymmetric Michael additions to nitroalkenes. Eur. J. Org. Chem. 2002, 1877-1894 (2002).
40. Bock, D. A., Lehmann, C. W. & List, B. Crystal structures of proline-derived enamines. Proc. Natl Acad. Sci. USA 107, 20636-20641 (2010).
41. Luo, S., Li, J., Zhang, L., Xu, H. & Cheng, J. P. Noncovalently supported heterogeneous chiral amine catalysts for asymmetric direct aldol and Michael addition reactions. Chem. Eur. J. 14, 1273-1281 (2008).
42. Wang, C. A. et al. Bottom-up embedding of the Jorgensen-Hayashi catalyst into a chiral porous polymer for highly efficient heterogeneous asymmetric organocatalysis. Chem. Eur. J. 18, 6718-6723 (2012).