Characterization of porosity in organic and metal-organic macrocycles by hyperpolarized 129Xe NMR spectroscopy

Organic Letters

Volumn 7, Issue 16, 2005, Pages 3397-3400

  Campbell, Katie ^a   Ooms, Kristopher J ^a   Wasylishen, Roderick E ^a   Tykwinski, Rik R ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 23944460500     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050830n     Document Type: Article

References (38)

1. Eddaoudi, M.; Kim, J.; Rosi, N.; Vodak, D.; Wachter, J.; O'Keeffe, M.; Yaghi, O. M. Science (Washington, D.C.) 2002, 295, 469-472.
2. Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, 1989.
3. Chae, H. K.; Siberio-Pérez, D. Y.; Kim, J.; Go, Y.; Eddaoudi, M.; Matzger, A. J.; O'Keeffe, M.; Yaghi, O. M. Nature (London) 2004, 427, 523-527.
4. (a) Rowsell, J. L. C.; Yaghi, O. M. Micropor. Mesopor. Mater. 2004, 73, 3-14.
5. (b) Yaghi, O. M.; O'Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Nature (London) 2003, 423, 705-714.
6. Uemura, T.; Kitagawa, S. Chem. Lett. 2005, 34, 132-137.
7. (a) Demers, E.; Maris, T.; Wuest, J. D. Cryst. Growth Des. 2005, 5, 1227-1235.
8. (b) Malek, N.; Maris, T.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 2005, 127, 5910-5916.
9. (a) Höger, S. In Acetylene Chemistry: Chemistry, Biology, and Material Science; Diederich, F., Stang, P. J., Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, 2005; Chapter 10.
10. (b) Tobe, Y.; Sonoda, M. In Modern Cyclophane Chemistry; Gleiter, R., Hopf, H., Eds.; Wiley-VCH: Weinheim, 2004; Chapter 1.
11. (c) Grave, C.; Schlüter, A. D. Eur. J. Org. Chem. 2002, 3075-3098.
12. See, for example: Grave, C.; Lentz, D.; Schäfer, A.; Samori, P.; Rabe, J. P.; Franke, P.; Schlüter, A. D. J. Am. Chem. Soc. 2003, 125, 6907-6918.
13. A number of studies have documented the analysis of coordination polymers or related species following either the removal or exchange of cocrystallized solvent; see refs 4-6 and citations therein.
14. 129Xe NMR experiment by a factor of approximately 10 000 and thus offers a method that can efficiently provide spectroscopic measurements for small quantities of sample over a broad temperature range; see: (a) Appelt, S.; Ben-Amar Baranga, A.; Erickson, C. J.; Romalis, M. V.; Young, A. R.; Happer, W. Phys. Rev. A 1998, 58, 1412-1439.
15. (b) Walker, T. G.; Happer, W. Rev. Mod. Phys. 1997, 69, 629-642.
16. Moudrakovski, I. L.; Wang, L.-Q.; Baumann, T.; Satcher, J. H., Jr.; Exarhos, G. J.; Ratcliffe, C. I.; Ripmeester, J. A. J. Am. Chem. Soc. 2004, 126, 5052-5053.
17. Bonardet, J.-L.; Fraissard, J.; Gédéon, A.; Springuel-Huet, M.-A. Catal. Rev. - Sci. Eng. 1999, 41, 115-225.
18. Meersmann, T.; Logan, J. W.; Simonutti R.; Caldarelli, S. Comotti A.; Sozzani, P.; Kaiser, L. G.; Pines, A. J. Phys. Chem. A 2000, 104, 11665-11670.
19. 129Xe chemical shift values that fall between ∼20-200 ppm (with respect to free Xe gas) can be correlated to Xe occupying space inside a porous solid; see: Terskikh, V. V.; Moudrakovski, I. L.; Breeze, S. R.; Lang, S.; Ratcliffe, C. I.; Ripmeester, J. A.; Sayari, A. Langmuir 2002, 18, 5653-5656.
20. (a) Ratcliffe, C. I. Annu. Rep. NMR Spectrosc. 1998, 36, 123-221.
21. (b) Goodson, B. M. J. Magn. Reson. 2002, 155, 157-216.
22. (c) Raftery, D.; Long, H.; Meersmann, T.; Grandinetti, P. J.; Reven, L.; Pines, A. Phys. Rev. Lett. 1991, 66, 584-587.
23. For consistency, the atoms in all crystal packing diagrams have been colored as follows: carbon (grey); nitrogen (red); platinum (blue); phosphorous (green); fluorine (yellow); sulfur (pink); oxygen (orange).
24. While the xenon distribution in the two sites as depicted by the contour map appears to be different, it is comparable. From the perspective shown in Figure 1d, the contour on the left represents xenon occupying a solvent site that is tilted with respect to the c-axis, which makes it appear larger.
25. Campbell, K.; Kuehl, C. J.; Ferguson, M. J.; Stang, P. J.; Tykwinski, R. R. J. Am. Chem. Soc. 2002, 124, 7266-7267.
26. 129Xe NMR spectrum of 1, see Supporting Information.
27. Xenon is known to preferentially occupy small cavities where the interaction potential with the host is minimized; see: Ripmeester, J. A.; Ratcliffe, C. I. J. Phys. Chem. 1990, 94, 7652-7656.
28. 129Xe NMR experiment.
29. Campbell, K.; McDonald, R.; Ferguson, M. J.; Tykwinski, R. R. Organometallics 2003, 22, 1353-1355.
30. Cavities are arranged in a spiral pattern through the solid. When viewed down the a-axis, the regions depicted by the contours in Figure 2e are not in the same plane as many of the atoms that appear to be overlapping the contours.
31. 129Xe NMR spectrum. This indicates that the solvent pores are inaccessible to xenon due to the trapping of the solvent in the structure.
32. (a) Ooms, K. J.; Wasylishen, R. E. Unpublished results.
33. (b) Jameson, C. J. J. Chem. Phys. 2002, 116, 8912-8929.
34. Campbell, K.; Tiemstra, N. M.; Prepas-Strobeck, N. S.; McDonald, R.; Ferguson, M. J.; Tykwinski, R. R. Synlett 2004, 182-186.
35. As a result of the disorder, the cocrystallized solvent molecules could not be refined, and it was not possible to crystallographically distinguish between dichloromethane and 1,2-dichloroethane.
36. Analysis of xenon dynamics, i.e., the exchange of xenon between different sites in these solids as a function of temperature, is an intriguing aspect of this characterization method that is currently being explored in more detail.
37. Moudrakovski, I. L.; Nossov, A.; Lang, S.; Breeze, S. R.; Ratcliffe, C. I.; Simard, B.; Santyr, G.; Ripmeester, J. A. Chem. Mater. 2000, 12, 1181-1183.
38. Jameson, C. J.; de Dios, A. C. J. Chem. Phys. 2002, 116, 3805-3821.