Coordinative self-assembly and solution-phase X-ray structural characterization of cavity-tailored porphyrin boxes

Journal of the American Chemical Society

Volumn 130, Issue 3, 2008, Pages 836-838

  Suk, Joong Lee ^a   Mulfort, Karen L ^a,b   Zuo, Xiaobing ^b   Goshe, Andrew J ^b   Wesson, Paul J ^c   Nguyen, SonBinh T ^a   Hupp, Joseph T ^a   Tiede, David M ^b  

^a NORTHWESTERN UNIVERSITY   (United States)

^b ARGONNE NATIONAL LABORATORY   (United States)

^c Northwestern University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; PORPHYRIN; TOLUENE;

ABSORPTION SPECTROSCOPY; ARTICLE; DIFFUSION COEFFICIENT; HYDRODYNAMICS; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SUPRAMOLECULAR CHEMISTRY; X RAY CRYSTALLOGRAPHY;

MOLECULAR STRUCTURE; PORPHYRINS; SOLUTIONS; X-RAY DIFFRACTION; ZINC;

EID: 38349174216     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja077661h     Document Type: Article

References (51)

1. (a) Leininger, S.; Olenyuk B.; Stang, P. J. Chem. Rev. 2000, 100, 853-908.
2. (b) Swiegers, G. F.; Malefetse, T. J. Chem. Rev. 2000, 100, 3483-3538.
3. (c) Riley, D. D. Chem. Rev. 1999, 99, 2573-2588.
4. (d) Fujita, M. Chem. Soc. Rev. 1998, 27, 417-425.
5. (e) Linton, B.; Hamilton, A. D. Chem. Rev. 1997, 97, 1669-1680.
6. (f) Stang, P. J.; Olenyuk, B. Acc. Chem. Res. 1997, 30, 502-518.
7. (a) Lee, S. J.; Hu, A.; Lin, W. J. Am. Chem. Soc. 2002, 124, 12948-12949.
8. (b) Schweiger, M.; Seidel, S. R.; Arif, A. M.; Stang, A. J. Inorg. Chem. 2002, 41, 2556-2559.
9. (c) Piotrowski, H.; Polborn, K.; Hilt, G.; Severin, K. J. Am. Chem. Soc. 2001, 123, 2699-2700.
10. (d) Navarro, A. J. R.; Lippert, B. Coord. Chem. Rev. 2001, 222, 219-250.
11. (e) Sautter, A.; Schmid, D. G.; Jung, G.; Würthner, F. J. Am. Chem. Soc. 2001, 123, 5424-5430.
12. (f) Cotton, F. A.; Lin, C.; Murillo, C. A. Inorg. Chem. 2001, 40, 575-577.
13. (g) Burini, A.; Bravi, R.; Fackler Jr., J. P.; Galassi, R.; Grant, T. A.; Omary, M. A.; Pietroni, B. R.; Staples, R. J. Inorg. Chem. 2000, 39, 3158-3165.
14. (h) Cotton, F. A.; Daniels, L. M.; Lin, C.; Murillo, C. A. J. Am. Chem. Soc. 1999, 121, 4538-4539.
15. (a) Manimaran, B.; Thanasekaran, P.; Rajendran, T.; Lin, R.-J.; Chang, I.-J.; Lee, G.-H.; Peng, S.-M.; Rajagopal, S.; Lu, K.-L. Inorg. Chem. 2002, 41, 5323-5325.
16. (b) Kuehl, C. J.; Huang, S. D.; Stang, P. J. J. Am. Chem. Soc. 2001, 123, 9634-9641.
17. (a) Campos-Fernandez, C. S.; Clerac, R.; Koomen, J. M.; Russell, D. H.; Dunbar, K. R. J. Am. Chem. Soc. 2001, 123, 773-774.
18. (b) MacDonnell, F. M.; Ali, M. M. J. Am. Chem. Soc. 2000, 122, 11527-11528.
19. (c) Habicher, T.; Nierengarten, J.-F.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. 1998, 37, 1916-1919.
20. (d) Saalfrank, R. W.; Bernt, I.; Uller, E.; Hampel, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 2482-2483.
21. (a) Fiedler, D.; Leung, D. H.; Bergman, R. G.; Raymond, K. N. Acc. Chem. Res. 2005, 38, 351-360.
22. (b) Yoshizawa, M.; Tamura, M.; Fujita, M. Science 2006, 312, 251-254.
23. (c) Sato, S.; Iida, J.; Suzuki, K.; Kawano, M.; Ozeki, T.; Fujita, M. Science 2006, 313, 1273-1276.
24. (a) Lee, S. J.; Lin, W. J. Am. Chem. Soc. 2002, 124, 4554-4555.
25. (b) Pak, J. J.; Greaves, J.; McCord, D. J.; Shea, K. J. Organometallics 2002, 21, 3552-3561.
26. (c) Liu, X.; Stern, C. L.; Mirkin, C. A. Organometallics 2002, 21, 1017-1019.
27. (d) Cotton, F. A.; Lin, C.; Murillo, C. A. J. Am. Chem. Soc. 2001, 123, 2670-2671.
28. Lee, S. J.; Hupp, J. T. Coord. Chem. Rev. 2006, 250, 1710-1723.
29. (a) Bélanger, S.; Hupp, J. T. Angew. Chem. 1999, 38, 2222-2224.
30. (b) Chang, S. H.; Chung, K. B.; Slone, R. V.; Hupp, J. T. Synth. Metals 2001, 117, 215-217.
31. (c) Williams, M. E.; Stevenson, K. J.; Massari, A. M.; Hupp, J. T. Anal. Chem. 2000, 72, 3122-3128.
32. (d) Merlau, M. L.; del Pilar Mejia, M.; Nguyen, S. T.; Hupp, J. T. Angew. Chem. 2001, 40, 4239-4242.
33. (e) Mines, G. A.; Tzeng, B.; Stevenson, K. J.; Li, J.; Hupp, J. T. Angew. Chem. 2002, 41, 154-157.
34. (f) Keefe, M. H.; O'Donnell, J. L.; Bailey, R. C.; Nguyen, S. T.; Hupp, J. T. Adv. Mater. 2003, 15, 1936-1939.
35. (g) Splan, K. E.; Massari, A. M.; Hupp, J. T. J. Phys. Chem. B 2004, 108, 4111-4115.
36. (h) Massari, A. M.; Gurney, R. W.; Schwartz, C. P.; Nguyen, S. T.; Hupp, J. T. Langmuir 2004, 20, 4422-4429.
37. (i) Libera, J.; Gurney, R.; Schwartz, C.; Jin, H.; Lee, T.-L.; Nguyen, S. T.; Hupp, J. T.; Bedzyk, M. J. Phys. Chem. B 2005, 109, 1441-1450.
38. (j) Martinson, A. B. F.; Massari, A. M.; Lee, S. J.; Gurney, R. W.; Splan, K. E.; Hupp, J. T.; Nguyen, S. T. J. Electrochem. Soc. 2006, 153, A527-A532.
39. Miljacic, L.; Sarkisov, L.; Ellis, D. E.; Snurr, R. Q. J. Chem. Phys. 2004, 121, 7228-7236.
40. Fan, J.; Whitehold, J. A.; Olenyuk, B.; Levin, M. D.; Stang, P. J.; Fleischer, E. B. J. Am. Chem. Soc. 1999, 121, 2741-2752.
41. 5b,c can be viewed as alternative solutions to the "torsion problem".
42. (a) Wilson, G. S.; Anderson, H. L. Chem. Commun. 1999, 1539-1540.
43. (b) Taylor, P. N.; Anderson, H. L. J. Am. Chem. Soc. 1999, 121, 11538-11545.
44. (c) Anderson, H. L. Chem. Commun. 1999, 2323-2330.
45. (a) O'Donnell, J. L. Zuo, X. Goshe, A. J.; Hupp J. T.; Tiede, D. M. J. Am. Chem. Soc. 2007, 129, 1578-1585.
46. (b) Lee, S. J.; Mulfort, K. L.; O'Donnell, J. L.; Zuo, X.; Goshe, A. J.; Wesson, P. J.; Nguyen, S. T.; Hupp, J. T.; Tiede, D. M. Chem. Commun. 2006, 4581-4583.
47. (c) Megyes, T.; Jude, H.; Grosz, T.; Bako, I.; Radnai, T.; Tarkanyi, G.; Palinkas G.; Stang, P. J. J. Am. Chem. Soc. 2005, 127, 10731-10738.
48. (d) Tiede, D. M.; Zhang, R. T.; Chen, L. X.; Yu, L. H.; Lindsey, J. S. J. Am. Chem. Soc. 2004, 126, 14054-14062.
49. Guinier A.; Fournet, G. In Small-Angle Scattering of X-rays; Wiley: New York, 1955. Data were also collected at wide angles (WAXS) as they can yield information about metal-metal separation distances, as well as information about solvent ordering (e.g., refs 13a,b). WAXS data are included as SI. Current work is focused on separating the contributions.
50. s = kT/ 6πηa, was used to estimate hydrodynamic radii, a. In the equation, k is Boltzmann's constant, T is the absolute temperature, and η is the viscosity of the medium.
51. See, for example: Shivanyuk, A.; Rebek, J., Jr. J. Am. Chem. Soc. 2002, 124, 12074-12075. For a contrasting example of narcissistic self-sorting (four- and six-porphyrin assemblies), see ref 12a.