Constructing monocrystalline covalent organic networks by polymerization

Nature Chemistry

Volumn 5, Issue 10, 2013, Pages 830-834

  Beaudoin, Daniel ^a   Maris, Thierry ^a   Wuest, James D ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

NITROSO DERIVATIVE; POLYMER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ORGANIC CHEMISTRY; POLYMERIZATION; X RAY CRYSTALLOGRAPHY;

CHEMISTRY, ORGANIC; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; NITROSO COMPOUNDS; POLYMERIZATION; POLYMERS;

EID: 84884823926     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1730     Document Type: Article

References (28)

1. Stock, N. & Biswas, S. Synthesis of metal-organic frameworks (MOFs): routes to various MOF topologies, morphologies, and composites. Chem. Rev. 112, 933-969 (2012)
2. Meek, S. T., Greathouse, J. A. & Allendorf, M. D. Metal-organic frameworks: a rapidly growing class of versatile nanoporous materials. Adv. Mater. 23, 249-267 (2011)
3. Wuest, J. D. Engineering crystals by the strategy of molecular tectonics. Chem. Commun. 41, 5830-5837 (2005) (Pubitemid 43024123)
4. Jones, J. T. A. et al. Modular and predictable assembly of porous organic crystals. Nature 474, 367-371 (2011)
5. Mastalerz, M. & Oppel, I. M. Rational construction of an extrinsic porous molecular crystal with an extraordinary high specific surface area. Angew. Chem. Int. Ed. 51, 5252-5255 (2012)
6. Co?te', A. P. et al. Porous, crystalline, covalent organic frameworks. Science 310, 1166-1170 (2005)
7. Feng, X., Ding, X. & Jiang, D. Covalent organic frameworks. Chem. Soc. Rev. 41, 6010-6022 (2012)
8. Bunck, D. N. & Dichtel, W. R. Internal functionalization of three-dimensional covalent organic frameworks. Angew. Chem. Int. Ed. 51, 1885-1889 (2012)
9. 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)
10. Lanni, L. M., Tilford, R. W., Bharathy, M. & Lavigne, J. J. Enhanced hydrolytic stability of self-assembling alkylated two-dimensional covalent organic frameworks. J. Am. Chem. Soc. 133, 13975-13983 (2011)
11. Kuhn, P., Antonietti, M. & Thomas, A. Porous, covalent triazine-based frameworks prepared by ionothermal synthesis. Angew. Chem. Int. Ed. 47, 3450-3453 (2008)
12. Gowenlock, B. G., Maidment, M. J., Orrell, K. G., Prokes?, I. & Roberts, J. R. Nitrosoanisoles. Sensitive indicators of dimerisation criteria for C-nitrosoarenes. J. Chem. Soc. Perkin Trans. 2, 1904-1911 (2001)
13. Fletcher, D. A., Gowenlock, B. G. & Orrell, K. G. Structural investigations of Cnitrosobenzenes. Part 2.1 NMR studies of monomer-dimer equilibria including restricted nitroso group rotation in monomers. J. Chem. Soc. Perkin Trans. 2, 797-804 (1998)
14. Orrell, K. G.,S?ik, V. & Stephenson, D. Study of the monomer-dimer equilibrium of nitrosobenzene using multinuclear one-and two-dimensional NMR techniques. Magn. Res. Chem. 25, 1007-1011 (1987)
15. Azoulay, M. & Fischer, E. Low-temperature proton nuclear magnetic resonance and ultraviolet absorption spectra and photochemistry of the system nitrosobenzene-azodioxybenzene and its methyl derivatives. J. Chem. Soc. Perkin Trans. 2, 637-642 (1982)
16. Fletcher, D. A. et al. Structural investigations of C-nitrosobenzenes. Part 3. Solidstate and solution 13C NMR studies, and crystal structure of E-(4-ClC6H4NO)2. J. Chem. Res. (S), 1999, 202-203 (1999)
17. Hoffmann, R., Gleiter, R. & Mallory, F. B. Non-least-motion potential surfaces. Dimerization of methylenes and nitroso compounds. J. Am. Chem. Soc. 92, 1460-1466 (1970)
18. Lu?ttke, W., Skancke, P. N. & Traetteberg, M. On the dimerization process of nitroso compounds. Theor. Chim. Acta 87, 321-333 (1994)
19. Gowenlock, B. G. & Richter-Addo, G. B. Dinitroso and polynitroso compounds. Chem. Soc. Rev. 34, 797-809 (2005) (Pubitemid 41306031)
20. Hacker, N. P. Investigation of the polymerization of 1,4-dinitrosobenzene by low-temperature infrared and UV absorption spectroscopy. Macromolecules 26, 5937-5942 (1993)
21. Fetizon, M. & Golfier, M. Oxydation se'lective des alcools par le carbonate d'argent. C. R. Acad. Sci. Ser. C 267, 900-903 (1968)
22. Maassen, J. A. & de Boer, T. J. Silver carbonate, a convenient reagent for preparing C-nitroso compounds from hydroxylamines. Recl. Trav. Chim. Pays-Bas 90, 373-376 (1971)
23. Beaudoin, D. & Wuest, J. D. Synthesis of N-arylhydroxylamines by Pd-catalyzed coupling. Tetrahedron Lett. 52, 2221-2223 (2011)
24. Spek, A. L. in PLATON, A Multipurpose Crystallographic Tool (Utrecht University, 2001)
25. van der Sluis, P. & Spek, A. L. BYPASS: an effective method for the refinement of crystal structures containing disordered solvent regions. Acta Crystallogr. A46, 194-201 (1990)
26. Lukose, B., Kuc, A. & Heine, T. The structure of layered covalent-organic frameworks. Chem. Eur. J. 17, 2388-2392 (2011)
27. Hasell, T., Chong, S. Y., Jelfs, K. E., Adams, D. J. & Cooper, A. I. Porous organic cage nanocrystals by solution mixing. J. Am. Chem. Soc. 134, 588-598 (2012)
28. Simard, M., Su, D. & Wuest, J. D. Use of hydrogen bonds to control molecular aggregation. Self-assembly of three-dimensional networks with large chambers. J. Am. Chem. Soc. 113, 4696-4698 (1991)