Molecular docking sites designed for the generation of highly crystalline covalent organic frameworks

Nature Chemistry

Volumn 8, Issue 4, 2016, Pages 310-316

  Ascherl, Laura ^a   Sick, Torben ^a   Margraf, Johannes T ^b   Lapidus, Saul H ^c   Calik, Mona ^a   Hettstedt, Christina ^a   Karaghiosoff, Konstantin ^a   Döblinger, Markus ^a   Clark, Timothy ^b   Chapman, Karena W ^c   Auras, Florian ^a   Bein, Thomas ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^c ARGONNE NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84961577154     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.2444     Document Type: Article

References (35)

1. Doonan, C. J., Tranchemontagne, D. J., Glover, T. G., Hunt, J. R. & Yaghi, O. M. Exceptional ammonia uptake by a covalent organic framework. Nature Chem. 2, 235-238 (2010).
2. 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).
3. 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).
4. Dogru, M. et al. A photoconductive thienothiophene-based covalent organic framework showing charge transfer towards included fullerene. Angew. Chem. Int. Ed. 52, 2920-2924 (2013).
5. Calik, M. et al. Extraction of photogenerated electrons and holes from a covalent organic framework integrated heterojunction. J. Am. Chem. Soc. 136, 17802-17807 (2014).
6. Patwardhan, S., Kocherzhenko, A. A., Grozema, F. C. & Siebbeles, L. D. A. Delocalization and mobility of charge carriers in covalent organic frameworks. J. Phys. Chem. C 115, 11768-11772 (2011).
7. Jin, S. et al. Charge dynamics in a donor-acceptor covalent organic framework with periodically ordered bicontinuous heterojunctions. Angew. Chem. Int. Ed. 52, 2017-2021 (2013).
8. Bertrand, G. H. V., Michaelis, V. K., Ong, T.-C., Griffin, R. G. & Dinca, M. Thiophene-based covalent organic frameworks. Proc. Natl Acad. Sci. USA 110, 4923-4928 (2013).
9. Coˆte, A. P. et al. Porous, crystalline, covalent organic frameworks. Science 310, 1166-1170 (2005).
10. Spitler, E. L. & Dichtel, W. R. Lewis acid-catalysed formation of two-dimensional phthalocyanine covalent organic frameworks. Nature Chem. 2, 672-677 (2010).
11. 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).
12. Spitler, E. L. et al. Lattice expansion of highly oriented 2D phthalocyanine covalent organic framework films. Angew. Chem. Int. Ed. 51, 2623-2627 (2012).
13. Medina, D. D. et al. Oriented thin films of a benzodithiophene covalent organic framework. ACS Nano 8, 4042-4052 (2014).
14. Medina, D. D. et al. Room temperature synthesis of covalent-organic framework films through vapor-assisted conversion. J. Am. Chem. Soc. 137, 1016-1019 (2015).
15. Uribe-Romo, F. J. et al. A crystalline imine-linked 3-D porous covalent organic framework. J. Am. Chem. Soc. 131, 4570-4571 (2009).
16. Wan, S. et al. Covalent organic frameworks with high charge carrier mobility. Chem. Mater. 23, 4094-4097 (2011).
17. Guo, J. et al. Conjugated organic framework with three-dimensionally ordered stable structure and delocalized π clouds. Nature Commun. 4, 2736 (2013).
18. Fang, Q. et al. Designed synthesis of large-pore crystalline polyimide covalent organic frameworks. Nature Commun. 5, 4503 (2014).
19. Jackson, K. T., Reich, T. E. & El-Kaderi, H. M. Targeted synthesis of a porous borazine-linked covalent organic framework. Chem. Commun. 48, 8823-8825 (2012).
20. Kuhn, P., Antonietti, M. & Thomas, A. Porous, covalent triazine-based frameworks prepared by ionothermal synthesis. Angew. Chem. Int. Ed. 47, 3450-3453 (2008).
21. Zhang, Y.-B. et al. Single-crystal structure of a covalent organic framework. J. Am. Chem. Soc. 135, 16336-16339 (2013).
22. Jones, J. T. A. et al. Modular and predictable assembly of porous organic molecular crystals. Nature 474, 367-371 (2011).
23. 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).
24. Shinde, D. B., Kandambeth, S., Pachfule, P., Kumar, R. R. & Banerjee, R. Bifunctional covalent organic frameworks with two dimensional organocatalytic micropores. Chem. Commun. 51, 310-313 (2014).
25. Spitler, E. L. et al. A 2D covalent organic framework with 4.7-nm pores and insight into its interlayer stacking. J. Am. Chem. Soc. 133, 19416-19421 (2011).
26. Dogru, M. & Bein, T. On the road towards electroactive covalent organic frameworks. Chem. Commun. 50, 5531-5546 (2014).
27. Zhou, T.-Y., Xu, S.-Q., Wen, Q., Pang, Z.-F. & Zhao, X. One-step construction of two different kinds of pores in a 2D covalent organic framework. J. Am. Chem. Soc. 136, 15885-15888 (2014).
28. Hasell, T., Schmidtmann, M., Stone, C. A., Smith, M. W. & Cooper, A. I. Reversible water uptake by a stable imine-based porous organic cage. Chem. Commun. 48, 4689-4691 (2012).
29. Clark, S. J. et al. First principles methods using CASTEP. Z. Kristallogr. 220, 567-570 (2005).
30. Perdew, J. P., Burke, K. & Ernzerhof, M. Generalized gradient approximation made simple. Phys. Rev. Lett. 77, 3865-3868 (1996).
31. Monkhorst, H. J. & Pack, J. D. Special points for Brillouin-zone integrations. Phys. Rev. B 13, 5188-5192 (1976).
32. McNellis, E. R., Meyer, J. & Reuter, K. Azobenzene at coinage metal surfaces: role of dispersive van der Waals interactions. Phys. Rev. B 80, 205414 (2009).
33. Tkatchenko, A. & Scheffler, M. Accurate molecular van der Waals interactions from ground-state electron density and free-atom reference data. Phys. Rev. Lett. 102, 073005 (2009).
34. Sing, K. S. W. et al. Reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity. Pure Appl. Chem. 57, 603-619 (1985).
35. Thommes, M. Physical adsorption characterization of nanoporous materials. Chem. Ing. Tech. 82, 1059-1073 (2010).