Variable pore size, variable chemical functionality, and an example of reactivity within porous phenylacetylene silver salts

Journal of the American Chemical Society

Volumn 121, Issue 36, 1999, Pages 8204-8215

  Kiang, Y H ^a   Gardner, Geoffrey B ^a   Lee, Stephen ^a   Xu, Zhengtao ^a   Lobkovsky, Emil B ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; BENZONITRILE; LIGAND;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; MOLECULAR DYNAMICS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0033568015     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991100b     Document Type: Article

References (84)

1. MacNicol, D. D.; McKendrick, J. J.; Wilson, D. R. In Inclusion Compounds; Atwood, J. L., Davies, J. E., MacNicol, D. D., Eds.; Academic Press: London, 1984; Vol. 2.
2. Hoskins, B. F.; Robson R. J. Am. Chem. Soc. 1990, 112, 1546.
3. Abrahams, B. F.; Hoskins, B. F.; Lin, J.; Robson R. J. Am. Chem. Soc. 1991, 113, 3045.
4. Simard, M.; Su, D.; Wuest, J. D. J. Am. Chem. Soc. 1991, 113, 4696.
5. Ermer, O.; Lindenberg, L. Helv. Chim. Acta 1991, 74, 825.
6. Fujuta, M.; Kwon, Y. J.; Washizu, S.; Ogura, K. J. Am. Chem. Soc. 1994, 116, 1151.
7. Abrahams, B. F.; Hoskins, B. F.; Michail, D. M.; Robson, R. Nature 1994, 369, 727.
8. Gardner, G. B.; Venkataraman, D.; Moore, J. S.; Lee, S. Nature 1995, 374, 792.
9. Venkataraman, D.; Gardner, G. B.; Lee, S.; Moore, J. S. J. Am. Chem. Soc. 1995, 117, 11600.
10. Ung, A.; Gizachew, D.; Bishop, R.; Scudder, M.; Dance, I.; Craig, D. J. Am. Chem. Soc. 1995, 117, 8475.
11. Endo, K.; Sawaki, T.; Koyanagi, M.; Kobayashi, K.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1995, 117, 8341.
12. Lu, J.; Harrison, W. T. A.; Jacobson, A. J. Angew. Chem. 1995, 107, 2759; Angew. Chem., Int. Ed. Engl. 1995, 34, 2557.
13. Lu, J.; Harrison, W. T. A.; Jacobson, A. J. Angew. Chem. 1995, 107, 2759; Angew. Chem., Int. Ed. Engl. 1995, 34, 2557.
14. Dolbeq, A.; Boubekeur, K.; Batail, P.; Canadell, E.; Aubansenzier, P.; Coulon, C.; Lerstrup, K. Mater. Chem. 1995, 5, 1707.
15. Gardner, G. B.; Kiang, Y.-H.; Lee, S.; Asgaonkar, A.; Venkataraman, D. J. Am. Chem. Soc. 1996, 118, 6946.
16. Yaghi, O. M.; Li, H.; Groy, T. L. J. Am. Chem. Soc. 1996, 118, 9096.
17. Brunet, P.; Simard, M.; Wuest, J. D. J. Am. Chem. Soc. 1997, 119, 2737.
18. Yaghi, O. M.; Davis, C. E.; Li, G.; Li, H. J. Am. Chem. Soc. 1996, 119, 2861.
19. Hoskins, B. F.; Robson, R.; Slizys, D. A. Angew. Chem., Int. Ed. 1997, 36, 2336
20. MacGillivray, L.; Atwood, J. Nature 1997, 389, 496.
21. Fujita, M.; Aoyagi, M.; Ogura, K. Bull. Chem. Soc. Jpn. 1998, 71, 1799.
22. Batten, S. R.; Robson, R. Angew. Chem., Int. Ed. 1998, 37, 1461.
23. Abrahams, B. F.; Jackson, P. A.; Robson, R. Angew. Chem., Int. Ed. 1998, 37, 2656.
24. Russel, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science (Washington, D.C.) 1997, 276, 575.
25. Copp, S. B.; Subramanian, S.; Zawortko, M. J. Am. Chem. Soc. 1992, 114, 8719.
26. Ermer, O.; Eling, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 829.
27. Michaelides, A.; Kiritsis, V.; Skoulika, S.; Aubry, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1495.
28. Reddy, D. S.; Craig, D. C.; Desiraju, G. R. J. Am. Chem. Soc. 1996, 118, 4090.
29. Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747.
30. Konoshita, Y.; Matsubara, I.; Higuchi, T.; Saito, Y. Bull. Chem. Soc. Jpn. 1959, 32, 1221.
31. Ermer, O. Adv. Mater. 1991, 3, 608.
32. Sinzger, K.; Hünig, S.; Jopp, M.; Bauer, D.; Bietsch, W.; von Shütz, J. U.; Wolf, H. C.; Kremer, R. K.; Metzenthin, T.; Bau, R.; Kahn, S. I.; Lindbaum, A.; Lengauer, C. L.; Tillmanns, E. J. Am. Chem. Soc. 1993, 115, 7696.
33. Hirsch, K. A.; Venkataraman, D.; Wilson, S. R.; Moore, J. S.; Lee, S. J. Chem. Soc., Chem. Commun. 1995, 2199.
34. Fujita, M.; Kwon, Y.; Sasaki, O.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 7287.
35. Bishop, R.; Choudhury, S.; Dance, I. J. Chem. Soc., Perkin Trans. 2 1982, 1159.
36. Kitagawa, S.; Munakata, M.; Tanimura, T. Inorg. Chem. 1992, 31, 1714.
37. Kitagawa, S.; Katawa, S.; Kondo, M.; Nozaka, Y.; Munakata, M. Bull. Chem. Soc. Jpn. 1993, 66, 3387
38. Carlucci, L.; Ciani, G.; Proserpio, D.; Sironi, A. Angew. Chem. 1995, 107, 2037; Angew. Chem., Int. Ed. Engl. 1995, 34, 1895.
39. Carlucci, L.; Ciani, G.; Proserpio, D.; Sironi, A. Angew. Chem. 1995, 107, 2037; Angew. Chem., Int. Ed. Engl. 1995, 34, 1895.
40. Carlucci, L.; Ciani, G.; Proserpio, D.; Sironi, A. J. Chem. Soc., Chem. Commun. 1996, 1393.
41. Dǔrčanská, E.; Jamnický, M.; Koman, M.; Wnek, I.; Glowiak, T. Acta. Crystallogr., Sect. C 1986, 42, 1157.
42. Dǔrčanská, E.; Koman, M.; Jamnický, M. Acta. Crystallogr., Sect. C 1991, 47, 1193.
43. Drew, M.; Gray, N.; Cabral, M.; Cabral, J. Acta. Crystallogr., Sect. C 1985, 41, 1434.
44. Nassimbeni, L.; Niven, M.; Taylor, M. Acta. Crystallogr., Sect. B 1990, 46, 354.
45. Bishop, R.; Craig, D.; Scudder, M. J. Chem. Soc., Perkin Trans. 2 1989, 1473.
46. Hawkins, S.; Scudder, M.; Craig, D.; Rae, A. D.; Raof, A.; Bishop, R.; Dance, I. J. Chem. Soc., Perkin Trans. 2 1990, 855.
47. Hawkins, S.; Bishop, R.; Craig, D.; Dance, I.; Rae, A. D.; Scudder, M. J. Chem. Soc., Perkin Trans. 2 1993, 1737.
48. Bishop, R.; Craig, D.; Dance, I.; Scudder, M.; Marchard, A.; Wang, Y. J. Chem. Soc., Perkin Trans. 2 1993, 937.
49. Mallick, M.; Bishop, R.; Craig, D.; Dance, I.; Scudder, M. Aust. J. Chem. 1991, 44, 343.
50. Ahn, P.; Bishop, R.; Craig, D. C.; Downing, G. A.; Scudder, M. L. Aust. J. Chem. 1997, 50, 1053.
51. Konnert, J.; Britton, D. Inorg. Chem. 1966, 5, 1193.
52. Hoskins, B. F.; Robson R. J. Am. Chem. Soc. 1989, 111, 5962.
53. Abrahams, B. F.; Batten, S. R.; Hamit, H.; Hoskins, B. F.; Robson, R. J. Chem. Soc., Chem. Commun. 1996, 1313.
54. Venkataraman, D.; Lee, S.; Moore, J. S.; Zhang, P.; Hirsch, K. A.; Gardner, G. B.; Covey, A. C.; Prentice, C. L. Chem. Mater. 1996, 8, 2030.
55. Fujita, M.; Ibukuro, F.; Yamaguchi, K.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 4175.
56. Yaghi, O. M.; Li, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 207.
57. Fujita, M.; Aoyagi, M.; Ibukuro, F.; Ogura, K.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 611.
58. Su, D.; Wang, X.; Simard, M.; Wuest, J. D. Supramol. Chem. 1995, 6, 171.
59. Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. Inorg. Chem. 1995, 34, 5698.
60. Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Am. Chem. Soc. 1995, 117, 4562.
61. Otieno, T.; Rettig, S. J.; Thompson, R. C.; Trotter, J. Inorg. Chem. 1993, 32, 1607.
62. Otieno, T.; Rettig, S. J.; Thompson, R. C.; Trotter, J. J. Can. Chem. 1989, 67, 1964.
63. Otieno, T.; Rettig, S. J.; Thompson, R. C.; Trotter, J. J. Can. Chem. 1990, 68, 1901.
64. MacGillivray, L. R.; Subramanian, S.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1994, 11, 1325.
65. Cromer, D. T.; Larson, A. C. Acta. Crystallogr. 1972, B28, 1052.
66. Carlucci, L.; Ciani, G.; Proserpio, D. M.; Sironi, A. J. Chem. Soc., Chem. Commun. 1994, 2755.
67. Kuroda-Sowa, T.; Horino, T.; Yamamoto, M.; Ohno, Y.; Maekawa, M.; Munakata, M. Inorg. Chem. 1997, 36, 6382.
68. Venkataraman, D.; Gardner, G. B.; Covey, A. C.; Lee, S.; Moore, J. S. Acta Crystallogr. 1996, 52, 2416.
69. Lopez, S.; Kahraman, M.; Harmata, M.; Keller, S. W. Inorg. Chem. 1997, 36, 6138.
70. Lu, J.; Crisci, G.; Niu, T.; Jacobson, A. J. Inorg. Chem. 1997, 36, 5140.
71. Hirsch, K. A.; Wilson, S. R.; Moore, J. S. Chem. Eur. J. 1997, 3, 765.
72. Blake, A. J.; Champness, N. R.; Khlobystov, A.; Lemenovskii, D. A.; Li, W.-S.; Schroder, M. J. Chem. Soc., Chem. Commun. 1997, 2027.
73. Abrahams, B. F.; Hardie, M. J.; Hoskins, B. F.; Robson, R.; Sutherland, E. E. J. Chem. Soc., Chem. Commun. 1994, 1049.
74. Schwer, H.; Keller, E.; Krämer, V. Z. Z. Kristallogr. 1993, 204, 203.
75. Takahashi, S.; Kuroyama, Y.; Sonogashi, K.; Hagihara, N. Synthesis 1980, 8, 627.
76. Lavastre, O.; Cabioch, S.; Dixneuf, P. H. Tetrahedron 1997, 53, 7595.
77. For 7, the starting material was the triiodide (1S,2S,5S)-Myrtanoxy-2,4,6-triiodobenzene, and for 3 and 7, the trihalides were directly reacted with the 4-ethynylbenzonitrile to make the desired final products. See the Experimental Section for specific reactions.
78. In this paper the a cell axis is pointed consistently in the direction of the channels. Were the structure truly hexagonal, the a axis would then be (unconventionally) the unique axis.
79. March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992; p 21.
80. Kondo, M.; Okubo, T.; Asami, A.; Noro, S.; Yoshitomi, T.; Kitagawa, S.; Ishii, T.; Matsuzaka, H.; Seki, K. Angew. Chem., Int. Ed. 1999, 38, 140.
81. Li, H.; Davis, C. E.; Groy, T. L.; Kelly, D. G.; Yaghi, O. M. J. Am. Chem. Soc. 1998, 120, 2186.
82. Li, H.; Eddaoudi, M.; Groy, T. L.; Yaghi, O. M. J. Am. Chem. Soc. 1998, 120, 8571.
83. Chui, S.; Lo, S.; Charmant, J.; Orpen, A. G.; Williams, I. D. Science (Washington, D.C.) 1999, 283, 1148.
84. Kresge, C. T.; Leonowicz, M. E.; Roth, W. J.; Vartuli, J. C.; Beck, J. S. Nature 1992, 359, 710.