A metal-organic framework with covalently bound organometallic complexes

Journal of the American Chemical Society

Volumn 132, Issue 27, 2010, Pages 9262-9264

  Oisaki, Kounosuke ^a,c   Li, Qiaowei ^a   Furukawa, Hiroyasu ^a   Czaja, Alexander U ^b   Yaghi, Omar M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b BASF SE   (Germany)

^c UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COVALENTLY BOUND; METAL ORGANIC FRAMEWORK; N-HETEROCYCLIC CARBENES; ORGANOMETALLIC COMPLEX; TYPE STRUCTURES; X-RAY STUDIES;

CARBON INORGANIC COMPOUNDS;

ORGANOMETALLICS;

METAL ORGANIC FRAMEWORK; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; COVALENT BOND; CRYSTAL STRUCTURE; X RAY CRYSTALLOGRAPHY;

EID: 77955809099     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja103016y     Document Type: Article

References (49)

1. (a) Yaghi, O. M.; O'Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Nature 2003, 423, 705-714.
2. (b) Kitagawa, S.; Kitaura, R.; Noro, S. Angew. Chem., Int. Ed. 2004, 43, 2334-2375.
3. (c) Férey, G. Chem. Soc. Rev. 2008, 37, 191-214.
4. (d) Czaja, A. U.; Trukhan, N.; Müller, U. Chem. Soc. Rev. 2009, 38, 1284-1293.
5. (e) Müller, U.; Schubert, M. M.; Yaghi, O. M. Handbook of Heterogeneous Catalysis, 2nd ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2008; Vol. 1, pp 247-262.
6. Wang, Z.; Cohen, S. M. Chem. Soc. Rev. 2009, 38, 1315-1329.
7. Postsynthetic modifications producing immobilized transition metal coordination complexes: (a) Wu, C.-D.; Hu, A.; Zhang, L.; Lin, W. J. Am. Chem. Soc. 2005, 127, 8940-8941.
8. (b) Ingelson, M. J.; Barrio, J. P.; Guilbaud, J.-B.; Khimyak, Y. Z.; Rosseinsky, M. J. Chem. Commun. 2008, 2680-2682.
9. (c) Kaye, S. S.; Long, J. R. J. Am. Chem. Soc. 2008, 130, 806-807.
10. (d) Doonan, C. J.; Morris, W.; Furukawa, H.; Yaghi, O. M. J. Am. Chem. Soc. 2009, 131, 9492-9493.
11. (e) Tanabe, K. K.; Cohen, S. M. Angew. Chem., Int. Ed. 2009, 48, 7424-7427.
12. Yamada, T.; Kitagawa, H. J. Am. Chem. Soc. 2009, 131, 6312-6313.
13. (a) Nolan, S. P. N-Heterocyclic Carbenes in Synthesis; Wiley-VCH: Weubgeunm, Germany, 2006.
14. (b) Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed. 2008, 47, 3122-3172.
15. (c) Marion, N.; Nolan, S. P. Acc. Chem. Res. 2008, 41, 1440-1449.
16. Cu (I)-NHC bond formation during MOF synthesis with use of a bent link: (a) Chun, J.; Jung, I. G.; Kim, H. J.; Park, M.; Lah, M. S.; Son, S. U. Inorg. Chem. 2009, 48, 6353-6355.
17. (b) Chun, J.; Lee, H. S.; Jung, I. G.; Lee, S. W.; Kim, H. J.; Son, S. U. Organometallics 2010, 29, 1518-1521.
18. Imidazolium precursors integrated within MOF: (a) Fei, Z.; Geldbach, T. J.; Zhao, D.; Scopelliti, R.; Dyson, P. J. Inorg. Chem. 2005, 44, 5200-5202.
19. (b) Fei, Z.; Geldbach, T. J.; Scopelliti, R.; Dyson, P. J. Inorg. Chem. 2006, 45, 6331-6337.
20. (c) Han, L.; Zhang, S.; Wang, Y.; Yan, X.; Lu, X. Inorg. Chem. 2009, 48, 786-788.
21. (d) Lee, J. Y.; Roberts, J. M.; Farha, O. K.; Sarjeant, A. A.; Scheidt, K. A.; Hupp, J. T. Inorg. Chem. 2009, 48, 9971-9973.
22. (e) Crees, R. S.; Cole, M. L.; Hanton, L. R.; Sumby, C. J. Inorg. Chem. 2010, 49, 1712-1719.
23. Mancilha, F. S.; DaSilveira Neto, B. A.; Lopes, A. S.; Moreira, P. F., Jr.; Quina, F. H.; Goncalves, R. S.; Dupont, J. Eur. J. Org. Chem. 2006, 4924-4933.
24. Neto, B. A. D.; Lopes, A. S.; Wust, M.; Costa, V. E. U.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2005, 46, 6843-6846.
25. See Supporting Information for details.
26. 2 = 0.1389 (all data), and GOF = 0.950.
27. (a) Eddaoudi, M.; Kim, J.; Rosi, N.; Vodak, D.; Wachter, J.; O'Keeffe, M.; Yaghi, O. M. Science 2002, 295, 469-472.
28. (b) Bae, Y.-S.; Dubbeldam, D.; Nelson, A.; Walton, K. S.; Hupp, J. T.; Snurr, R. Q. Chem. Mater. 2009, 21, 4768-4777.
29. O'Keeffe, M.; Peskov, M. A.; Ramsden, S. J.; Yaghi, O. M. Acc. Chem. Res. 2008, 41, 1782-1789.
30. Examples of using metalloligands to produce heterometallic MOFs: (a) Kitaura, R.; Onoyama, G.; Sakamoto, H.; Matsuda, R.; Noro, S.; Kitagawa, S. Angew. Chem., Int. Ed. 2004, 43, 2684-2687.
31. (b) Halpar, S. R.; Do, L.; Stork, J. R.; Cohen, S. M. J. Am. Chem. Soc. 2006, 128, 15255-15268.
32. (c) Cho, S.-H.; Ma, B.; Nguyen, S. T.; Hupp, J. T.; Albrecht-Schmitt, T. E. Chem. Commun. 2006, 2563-2565.
33. (d) Szeto, K. C.; Lillerud, K. P.; Tilset, M.; Bjorgen, M.; Prestipino, C.; Zecchina, A.; Lamberti, C.; Bordiga, S. J. Phys. Chem. B 2006, 110, 21509-21520.
34. (e) Szeto, K. C.; Kongshaug, K. O.; Jakobsen, S.; Tilset, M.; Lillerud, K. P. Dalton Trans. 2008, 2054-2060.
35. Tranchmontagne, D. J.; Mendoza-Cortés, J. L.; O'Keeffe, M.; Yaghi, O. M. Chem. Soc. Rev. 2009, 38, 1257-1283.
36. 2O] calcd: C, 35. 77;
37. H, 2. 54;
38. I, 26. 99;
39. N, 4. 47;
40. Pd, 11. 32;
41. Zn, 9. 28. Found: C, 35.04;
42. H, 2. 62;
43. I, 26. 92;
44. N, 4. 71;
45. Pd, 9. 67;
46. Zn, 9. 32.
47. Selected example: Han, Y.; Huyuh, H. V.; Tan, G. K. Organometallics 2007, 26, 6447-6452.
48. (a) Chemical shifts of C2 of N, N'-dimethylbenzoimidazolium salt and a metal-free NHC generated from the salt are reported as 143 and 225 ppm, respectively: Tapu, D.; Dixon, D. A.; Roe, C. Chem. Rev. 2009, 109, 3385-3407.
49. 2 (L) has donor strength similar to that of pyridine: Huynh, H. V.; Han, Y.; Jothibasu, R.; Yang, J. A. Organometallics 2009, 28, 5394-5404.