Second-order self-organization in coordination-driven self-assembly: Exploring the limits of self-selection

Inorganic Chemistry

Volumn 47, Issue 23, 2008, Pages 11257-11268

  Northrop, Brian H ^a   Yang, Hai Bo ^b   Stang, Peter J ^a  

^a UNIVERSITY OF UTAH   (United States)

^b EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

MEMBRANE PROTEIN;

ARTICLE; BINDING SITE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

BINDING SITES; MAGNETIC RESONANCE SPECTROSCOPY; MEMBRANE PROTEINS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 57949087694     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic801711q     Document Type: Article

References (69)

1. (a) Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1990, 29, 1304.
2. (b) Lindsey, J. S. New. J. Chem. 1991, 15, 153.
3. (c) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154.
4. (d) Rebek, J., Jr Acc. Chem. Res. 1999, 32, 278.
5. (e) Yaghi, O. M.; O'Keeffe, M.; Ockwig, N. W.; Chae, H. K.; Eddaoudi, M.; Kim, J. Nature 2003, 423, 705.
6. (a) Orr, G. W.; Barbour, L. T.; Atwood, J. L. Science 1999, 285, 1049.
7. (b) Storhoff, J. J.; Mirkin, C. A. Chem. Rev. 1999, 99, 1849.
8. (c) Lehn, J.-M. Science 2002, 295, 2400.
9. (d) Lehn, J.-M. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4763.
10. (e) Lehn, J.-M. Rep. Prog. Phys. 2004, 67, 249.
11. (f) Hollingsworth, M. D. Science 2002, 295, 2410.
12. (a) Deitrich, B.; Lehn, J.-M.; Sauvage, J. P. Tetrahedron Lett. 1969, 34, 2889.
13. (b) Pederson, C. J. Ger. Offen, Application: DE 70-2015732, 1970.
14. (c) Lehn, J.-M.; Sauvage, J. P.; Dietrich, B. J. Am. Chem. Soc. 1970, 92, 2916.
15. (d) Cram, D. J.; Cram, J. M. Acc. Chem. Res. 1978, 11, 8.
16. (e) Lehn, J.-M. Acc. Chem. Res. 1978, 11, 49.
17. (f) Pederson, C. J.; Lehn, J.-M.; Cram, D. J. Resonance 2001, 6, 71.
18. (a) Gleick, J. Chaos: Making a New Science. Penguin: New York, 1988.
19. (b) Kauffman, S. At Home in the Universe; Oxford University Press: Oxford, U.K., 1995.
20. (a) Krämer, R.; Lehn, J.-M.; Marquis-Rigault, A. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5394.
21. (b) Smith, V.; Lehn, J.-M. Chem. Commun. 1996, 2733.
22. (c) Funeriu, D. P.; Lehn, J.-M.; Fromm, K. M.; Fenske, D. Chem. - Eur. J. 2000, 6, 2103.
23. (a) Albrecht, M.; Schneider, M.; Röttele, H. Angew. Chem., Int. Ed. 1999, 38, 557.
24. (b) Albrecht, M.; Schneider, M. Eur. J. Inorg. Chem. 2002, 1301.
25. (a) Caulder, D. L.; Raymond, K. N. Angew. Chem., Int. Ed. Engl. 1997, 36, 1440.
26. (b) Ziegler, M.; Miranda, J. J.; Anderson, U. N.; Johnson, D. W.; Leary, J. A.; Raymond, K. N. Angew. Chem., Int. Ed. 2001, 40, 733.
27. Masood, M. A.; Enemark, E. J.; Stack, T. D. P. Angew. Chem., Int. Ed. 1998, 37, 928.
28. Shi, X.; Fettinger, J. C.; Davis, J. T. J. Am. Chem. Soc. 2001, 123, 6738.
29. (a) Giuseppone, N; Schmitt, J.-L.; Lehn, J.-M. Angew. Chem., Int. Ed. 2004, 43, 4902.
30. (b) Giuseppone, N.; Lehn, J.-M. J. Am. Chem. Soc. 2004, 126, 11448.
31. (c) Giuseppone, N.; Fuks, G.; Lehn, J.-M. Chem. - Eur. J. 2006, 12, 1723.
32. (a) Caulder, D. L.; Powers, R. E.; Parac, T. N.; Raymond, K. N. Angew. Chem., Int. Ed. 1998, 37, 1840.
33. (b) Bruckner, C.; Powers, R. E.; Raymond, K. N. Angew. Chem., Int. Ed. 1998, 37, 1837.
34. (a) Schultz, D.; Nitschke, J. R. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 11191.
35. (b) Schultz, D.; Nitschke, J. R. Angew. Chem., Int. Ed. 2006, 45, 2453.
36. (c) Hutin, M.; Frantz, R.; Nitschke, J. R. Chem. - Eur. J. 2006, 12, 4077.
37. (d) Nitschke, J. R. Acc. Chem. Res. 2007, 40, 103.
38. (a) Severin, K. Chem. - Eur. J. 2004, 10, 2565.
39. (b) Saur, I.; Severin, K. Chem. Commun. 2005, 1471.
40. (c) Saur, I.; Scopelliti, R.; Severin, K. Chem. - Eur. J. 2006, 12, 1058.
41. (a) Barboiu, M.; Petit, E.; Vaughan, G. Chem. - Eur. J. 2004, 10, 2263.
42. (b) Dumitru, F.; Petit, E.; van der Lee, A.; Barboiu, M. Eur. J. Inorg. Chem. 2005, 4255.
43. (c) Barboiu, M.; Petit, E.; van der Lee, A.; Vaughan, G. Inorg. Chem. 2005, 44, 5649.
44. (d) Legrand, Y.-M.; van der Lee, A.; Barboiu, M. Inorg. Chem. 2007, 46, 9540.
45. (a) Wu, A.; Isaacs, L. J. Am. Chem. Soc. 2003, 125, 4831.
46. (b) Mukhopadhyay, P.; Wu, A.; Isaacs, L. J. Org. Chem. 2004, 69, 6157.
47. (c) Lui, S.-M.; Ruspic, C.; Mukhopadhyay, P.; Chakrabarti, S.; Zavalij, P.; Isaacs, L. J. Am. Chem. Soc. 2005, 127, 15959.
48. (d) Mukhopadhyay, P.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2006, 128, 14903.
49. Taylor, P. N.; Anderson, H. L. J. Am. Chem. Soc. 1999, 121, 11538.
50. While the simultaneous self-assembly of nine components was studied, only eight supramolecules were obtained because two of the nine components were complementary constituents that self-assemble to form one single supramolecule.
51. Addicott, C.; Das, N.; Stang, P. J. Inorg. Chem. 2004, 43, 5335.
52. Yang, H.-B.; Ghosh, K.; Northrop, B. H.; Stang, P. J. Org. Lett. 2007, 9, 1561.
53. Zheng, Y.-R.; Yang, H.-B.; Northrop, B. H.; Ghosh, K.; Stang, P. J. Inorg. Chem. 2008, 47, 4706.
54. Zhao, L.; Northrop, B. H.; Zheng, Y.-R.; Yang, H.-B.; Lee, H. J.; Lee, Y. M.; Park, J. Y.; Chi, K.-W.; Stang, P. J. J. Org. Chem. 2008, 73, 6580-6586.
55. (a) Yang, H.-B.; Ghosh, K.; Northrop, B. H.; Zheng, Y.-R.; Lyndon, M. M.; Muddiman, D. C.; Stang, P. J. J. Am. Chem. Soc. 2007, 129, 14187.
56. (b) Ghosh, K.; Yang, H.-B.; Northrop, B. H.; Lyndon, M. M.; Zheng, Y.-R.; Muddiman, D. C.; Stang, P. J. J. Am. Chem. Soc. 2008, 130, 5320.
57. (a) Yang, H.-B.; Ghosh, K.; Zhao, Y.; Northrop, B. H.; Lyndon, M. M.; Muddiman, D. C.; White, H. S.; Stang, P. J. J. Am. Chem. Soc. 2008, 130, 839.
58. (b) Ghosh, K.; Zhao, Y.; Yang, H.-B.; Northrop, B. H.; White, H. S.; Stang, P. J. J. Org. Chem., published online October 8, 2008, DOI: 10.1021/jo801692y.
59. (a) Yang, H.-B.; Das, N.; Huang, F.; Hawkridge, A. M.; Muddiman, D. C.; Stang, P. J. J. Am. Chem. Soc. 2006, 128, 10014.
60. (b) Yang, H.-B.; Hawkridge, A. M.; Huang, S. D.; Das, N.; Bunge, S. D.; Muddiman, D. C.; Stang, P. J. J. Am. Chem. Soc. 2007, 129, 2120.
61. Northrop, B. H.; Glöckner, A.; Stang, P. J. J. Org. Chem. 2008, 73, 1787.
62. 2O (current study).
63. See, for example: (a) Jones, M. N.; Champan, D. Micelles, Monolayers and Biomembranes; Wiley-Liss: New York, 1995.
64. (b) Discler, D. E.; Eisenberg, A. Science 2002, 297, 967.
65. (c) Xia, Y.; Yang, P.; Sun, Y.; Wu, Y.; Mayers, B.; Gates, B.; Yin, Y.; Kim, F.; Han, H. Adv. Matter. 2003, 15, 353.
66. (d) Xia, Y.; Gates, B.; Yin, Y. D.; Lu, Y. Adv. Matter. 2000, 12, 693.
67. 2O used in this study is optimal for achieving quantitative self-assembly of rectangular metallacycles; therefore we chose not to vary the solvent in the current study.
68. Kryschenko, Y. K.; Seidel, S. R.; Arif, A. M.; Stang, P. J. J. Am. Chem. Soc. 2003, 125, 5193.
69. Kuehl, C. J.; Huang, S. D.; Stang, P. J. J. Am. Chem. Soc. 2001, 123, 9634.