Macrocycles with switchable exo/endo metal binding sites

Journal of the American Chemical Society

Volumn 131, Issue 48, 2009, Pages 17620-17629

  Tian, Lei Lei ^a   Wang, Chun ^a   Dawn, Sandipan ^a   Smith, Mark D ^a   Krause, Jeanette A ^b   Shimizu, Linda S ^a  

^a UNIVERSITY OF SOUTH CAROLINA   (United States)

^b UNIVERSITY OF CINCINNATI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING AFFINITIES; BIPYRIDINES; BOND ROTATIONS; COORDINATION COMPLEX; COORDINATION POLYMERS; MACROCYCLES; MACROCYCLICS; METAL BINDING SITES; METAL COMPLEXATION; METAL NITRATE; METAL ORGANIC FRAMEWORK; MULTIPLE CONFORMATIONS; SOLID-STATE STRUCTURES; SWITCHABLE; UREA GROUPS;

BINDING ENERGY; CADMIUM; CHROMIUM; CHROMIUM COMPOUNDS; COBALT COMPOUNDS; COORDINATION REACTIONS; FLUORINE CONTAINING POLYMERS; MANGANESE; MANGANESE COMPOUNDS; METAL COMPLEXES; METALS; ORGANOMETALLICS; SILVER; UREA; X RAY CRYSTALLOGRAPHY; ZINC;

BINDING SITES;

2,2' BIPYRIDINE DERIVATIVE; LIGAND; MACROCYCLIC COMPOUND; METAL COMPLEX; METAL ORGANIC FRAMEWORK; NITRATE; POLYMER;

ARTICLE; BINDING AFFINITY; BINDING SITE; CHEMICAL BOND; CHEMICAL STRUCTURE; CONFORMATION; CRYSTAL STRUCTURE; METAL BINDING; SOLID STATE; SYNTHESIS; TITRIMETRY; X RAY CRYSTALLOGRAPHY;

2,2'-DIPYRIDYL; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; FEASIBILITY STUDIES; MACROCYCLIC COMPOUNDS; METALS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ROTATION; SOLUTIONS; STEREOISOMERISM;

EID: 72249087335     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja906474z     Document Type: Article

References (83)

1. Seo, J.; Park, S.; Lee, S. S.; Fainerman-Melnikova, M.; Lindoy, L. F. Inorg. Chem. 2009, 48, 2770-2779.
2. Cazacu, A.; Tong, C.; Lee, A. V.; Fyles, T. M.; Barboiu, M. J. Am. Chem. Soc. 2006, 128, 9541-9548.
3. Shamsipur, M.; Hashemi, O. R.; Lippolis, V. J. Membr. Sci. 2006, 282, 322-327.
4. Barboiu, M.; Cerneaux, S.; van der Lee, A.; Vaughan, G. J. Am. Chem. Soc. 2004, 126, 3545-3550.
5. Sidorov, V.; Kotch, F. W.; Kuebler, J. L.; Lam, Y. F.; Davis, J. T. J. Am. Chem. Soc. 2003, 125, 2840-2841.
6. Kim, J. S.; Quang, D. T. Chem. Rev. 2007, 107, 3780-3799.
7. Lindoy, L. F. Dalton Trans. 2006, 43, 5115-5117.
8. Choi, K. H.; Hamilton, A. D. J. Am. Chem. Soc. 2003, 125, 10241-10249.
9. Gawley, R. E.; Pinet, S.; Cardona, C. M.; Datta, P. K.; Ren, T.; Guida, W. C.; Nydick, J.; Leblanc, R. M. J. Am. Chem. Soc. 2002, 124, 13448-13453.
10. Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486-516.
11. Deetz, M. J.; Shang, M.; Smith, B. D. J. Am. Chem. Soc. 2000, 122, 6201-6207.
12. Yang, X. G.; Knobler, C. B.; Zheng, Z. P.; Hawthorne, M. F. J. Am. Chem. Soc. 1994, 116, 7142-7159.
13. Bakirci, H.; Koner, A. L.; Dickman, M. H.; Kortz, U.; Nau, W. M. Angew. Chem., Int. Ed. 2006, 45, 7400-7404.
14. Izzet, G.; Douziech, E.; Prange, T.; Tomas, A.; Jabin, I.; Le Mest, Y.; Reinaud, O. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 6831-6836.
15. Arnaud-Neu, F.; Schewing-Weill, M.-J.; Dozol, J.-F. Calixarene for Nuclear Waste Treatment. In Calixarene 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, 2001; pp 642-662.
16. Kuhnert, N.; Burzlaff, N.; Patel, C.; Lopez-Periago, A. Org. Biomol. Chem. 2005, 3, 1911-1921.
17. Takemura, H. Curr. Org. Chem. 2005, 9, 521-533.
18. Kaplan, W. A.; Suslick, K. S.; Scott, R. A. J. Am. Chem. Soc. 1991, 113, 9824-9827.
19. Filby, M. H.; Steed, J. W. Coord. Chem. Rev. 2006, 250, 3200-3218.
20. Moore, J. S. Angew. Chem., Int. Ed. 2006, 45, 4416-4439.
21. MacLachlan, M. J. Pure Appl. Chem. 2006, 78, 873-888.
22. Hoger, S. Angew. Chem., Int. Ed. 2005, 44, 3806-3808.
23. Moore, J. S. Chem. Commun. 2003, 807-818.
24. Hodacova, J.; Budesinsky, M. Org. Lett. 2007, 9, 5641-5643.
25. Riddle, J. A.; Jiang, X.; Lee, D. W. Analyst 2008, 133, 417-422.
26. Misra, R.; Chandrashekar, T. K. Acc. Chem. Res. 2008, 41, 265-279.
27. Yang, J.; Dewal, M. B.; Profeta, S.; Smith, M. D.; Li, Y.; Shimizu, L. S. J. Am. Chem. Soc. 2008, 130, 612-621.
28. Dewal, M. B.; Xu, Y.; Yang, J.; Mohammed, F.; Smith, M. D.; Shimizu, L. S. Chem. Commun. 2008, 3909-3911.
29. Shimizu, L. S.; Hughes, A. D.; Smith, M. D.; Davis, M. J.; Zhang, B. P.; zur Loye, H.-C.; Shimizu, K. D. J. Am. Chem. Soc. 2003, 125, 14972-14973.
30. Eddaoudi, M.; Moler, D. B.; Li, H.; Chen, B.; Reineke, T. M.; O'Keefe, M.; Yaghi, O. M. Acc. Chem. Res. 2001, 34, 319-330.
31. Ockwig, M. W.; Delgado-Friedrich, O.; O'Keefe, M.; Yaghi, O. M. Acc. Chem. Res. 2005, 38, 176-182.
32. Ferey, G.; Mellot-Draznieks, C.; Serre, C.; Millange, F. Acc. Chem. Res. 2005, 38, 217-225.
33. Robson, R. J. Chem. Soc., Dalton Trans. 2000, 3735-3744.
34. Tranchemontagne, D. J.; Medoza-Cortes, J. L.; O'Keefe, M.; Yaghi, O. M. Chem. Soc. Rev. 2009, 38, 1257-1283.
35. Seo, J. S.; Whang, D.; Lee, H.; Jun, S. I.; Oh, J.; Jeon, Y. J.; Kin, K. Nature 2000, 404, 982-986.
36. Mulfort, K. L.; Hupp, J. T. J. Am. Chem. Soc. 2007, 129, 9604-9605.
37. Costa, J. S.; Gamez, P.; Black, C. A.; Roubeau, O.; Teat, S. J.; Reedik, J. Eur. J. Inorg. Chem. 2008, 1551-1554.
38. Wang, Z. Q.; Cohen, S. M. Angew. Chem., Int. Ed. 2008, 47, 4699-4702.
39. Wang, Z. Q.; Cohen, S. M. J. Am. Chem. Soc. 2007, 129, 12368-12369.
40. Dugan, E.; Wang, Z.; Okamura, M.; Medina, A.; Cohen, S. M. Chem. Commun. 2008, 3366-3368.
41. Albrecht, M. Chem. Rev. 2001, 101, 3457-3497.
42. Kaes, C.; Katz, A.; Hosseini, M. W. Chem. Rev. 2000, 100, 3553-3590.
43. Torrado, A.; Imperiali, B. J. Org. Chem. 1996, 61, 8940-8948.
44. Josceanu, A. M.; Moore, P.; Rawle, S. C.; Sheldon, P.; Smith, S. M. Inorg. Chim. Acta 1995, 240, 159-168.
45. Piguet, C.; Bernardinelli, G.; Hopfgartner, G. Chem. Rev. 1997, 97, 2005-2062.
46. Knof, U.; von Zelewsky, A. Angew. Chem., Int. Ed. 1999, 38, 302-322.
47. Belser, P.; Bernhard, S.; Jandrasics, E.; von Zelewsky, A.; DeCola, L.; Balzani, V. Coord. Chem. Rev. 1997, 159, 1-8.
48. Belser, P.; Bernhard, S.; Blum, C.; Beyeler, A.; De Cola, L.; Balzani, V. Coord. Chem. Rev. 1999, 190-192, 155-169.
49. Balzani, V.; Juris, A.; Venturi, M.; Campagna, S.; Serroni, S. Chem. Rev. 1996, 96, 759-833.
50. Baxter, S. M.; Jones, W. E.; Danielson, E.; Worl, L.; Strouse, G.; Younathan, J.; Meyer, T. J. Coord. Chem. Rev. 1991, 111, 47-71.
51. Kaes, C.; Hosseini, M. W.; Rickard, C. E. F.; Skelton, B. W.; White, A. H. Angew. Chem., Int. Ed. 1998, 37, 920-922.
52. Kaes, C.; Hosseini, M. W.; DeCian, A.; Fischer, J. Tetrahedron Lett. 1997, 38, 3901-3904.
53. Ibrahim, R.; Tsuchiya, S.; Ogawa, S. J. Am. Chem. Soc. 2000, 122, 12174-12185.
54. Tsuchiya, S.; Nakatani, Y.; Ibrahim, R.; Ogawa, S. J. Am. Chem. Soc. 2002, 124, 4936-4937.
55. De Mendoza, J.; Mesa, E.; Rodriguez-Ubis, J. C.; Vázquez, P.; Vögtle, F.; Windscheif, P. M.; Rissanen, K.; Lehn, J. M.; Lilienbaum, D.; Ziessel, R. Angew. Chem., Int. Ed. 1991, 30, 1331-1333.
56. Nitschke, J.; Tilley, T. D. J. Org. Chem. 1998, 63, 3673-3676.
57. Nitschke, J.; Zürcher, S.; Tilley, T. D. J. Am. Chem. Soc. 2000, 122, 10345-10352.
58. Nitschke, J.; Tilley, T. D. Angew. Chem., Int. Ed. 2001, 40, 2142-2145.
59. Henze, O.; Lentz, D.; Schafer, A.; Franke, P.; Schluter, A. D. Chem. - Eur. J. 2002, 8, 357-365.
60. The cavity size was calculated from the crystal structure provided by ref 59.
61. Baxter, P. N. W. J. Org. Chem. 2001, 66, 4170-4179.
62. Spartan 04 for Macintosh, v 1.1.1; Wavefunction, Inc.: Irvine, CA., 2007.
63. Distance between van der Waals surfaces of atoms was calculated as (internuclear distance)-(sum of van der Waals radii of atoms involved). The distance between the van der Waals surfaces of two opposite pyridyl nitrogen atoms.
64. Shannon, R. D. Acta Crystallogr., Sect. A: Found. Crystallogr. 1976, A32, 751-767.
65. Hunter, C. A. Angew. Chem., Int. Ed. 2004, 43, 5310-5324.
66. + • 2 complex formed within two weeks.
67. Comprehensive Coordination Chemistry; Wilkinson, G., Ed.; Pergamon: Oxford, 1987; Vol.5, p 786.
68. Khlobystov, A. N.; Blake, A. J.; Champness, N. R.; Lemenovskii, D. A.; Majouga, A. G.; Zyk, N. V.; Schröder, M. Coord. Chem. Rev. 2001, 222, 155-192.
69. Steel, P. J.; Fitchett, C. M. Coord. Chem. Rev. 2008, 252, 990-1006.
70. Ezuhara, T.; K.; Aoyama, Y. J. Am. Chem. Soc. 1999, 121, 3279-3283.
71. Xu, Y.; Han, L.; Lin, Z. Z.; Liu, C. P.; Yuan, D. Q.; Zhou, Y. F.; Hong, M. C. Eur. J. Inorg. Chem. 2004, 4457-4462.
72. Maggard, P. A.; Stern, C. L.; Poeppelmeier, K. R. J. Am. Chem. Soc. 2001, 123, 7742-7743.
73. Tarducci, C.; Badyal, J. P. S.; Brewer, S. A.; Willis, C. Chem. Commun. 2005, 406-408.
74. Kitagawa, S.; Kitaura, R.; Noro, S. Angew. Chem., Int. Ed. 2004, 43, 2334-2375.
75. Mueller, U.; Schubert, M.; Teich, F.; Puetter, H.; Schierle-Arndt, K.; Pastre, J. J. Mat. Chem. 2006, 16, 626-636.
76. Hirose, K. J. Inclusion Phenom. Macrocyclic Chem. 2001, 39, 193-209.
77. Gong, H. Y.; Wang, D. X.; Zheng, Q. Y.; Wang, M. X. Tetrahedron 2009, 65, 87-92.
78. Abe, Y.; Wada, G. Bull. Chem. Soc. Jpn. 1981, 54, 3334-3339.
79. Kaim, W. J. Am. Chem. Soc. 1982, 104, 3833-3837.
80. Tori, Y.; Yazaki, T.; Kaizu, Y.; Murasato, S.; Kobayashi, H. Bull. Chem. Soc. Jpn. 1969, 42, 2264-2267.
81. -1) in THF and MeOH mixed solution (v/v ) 99:1) by using a microsyringe. UV-vis absorption changes were monitored during the titration. The difference in absorbance (ΔA) of the host in the presence of the guest and absence of the guest was recorded, and the data were plotted against [guest].
82. Giansante, C.; Ceroni, P.; Venturi, M.; Balzani, V.; Sakamoto, J.; Schluter, A. D. Chem. - Eur. J. 2008, 14, 10772-10781.
83. Ravi, P.; Dai, S.; Tam, K. C. J. Phys. Chem. B 2005, 109, 22791-22798.