Factors influencing self-aggregation tendencies of cationic porphyrins in aqueous solution

Journal of the American Chemical Society

Volumn 122, Issue 31, 2000, Pages 7494-7502

  Kano, Koji ^a   Fukuda, Kazuya ^a   Wakami, Hideo ^a   Nishiyabu, Ryuhei ^a   Pasternack, Robert F ^b  

^a DOSHISHA UNIVERSITY   (Japan)

^b SWARTHMORE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; PORPHYRIN DERIVATIVE; POTASSIUM NITRATE; PYRIDINIUM DERIVATIVE; WATER;

AQUEOUS SOLUTION; ARTICLE; DIMERIZATION; ENTHALPY; ENTROPY; HYDROPHOBICITY; LIGHT SCATTERING; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PKA; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

EID: 0034625895     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000738g     Document Type: Article

References (57)

1. (a) For a review, see: White, W. I. In The Porphyrins; Dolphins, D., Ed.; Academic Press: New York, 1978; Vol. V, Chapter 7.
2. (b) For more recent papers, see: Schneider, H.-J.; Wang, M. J. Org. Chem. 1994, 59, 7464-7472 and references therein.
3. (a) Pasternack, R. F.; Huber, P. R.; Boyd, P.; Engasser, G.; Francesconi, L.; Gibbs, E.; Fasella, P.; Venturo, G. C.; Hinds, L. deC. J. Am. Chem. Soc. 1972, 94, 4511-4517.
4. (b) Krishnamurthy, M.; Sutler, J. R.; Hambright, P. J. Chem. Soc., Chem. Commun. 1975, 13-14.
5. (c) Chandrashekar, T. K.; Van Willigen, H.; Ebersole, M. H. J. Phys. Chem. 1984, 88, 4326-4332.
6. (a) Ohno, O.; Kaizu, Y.; Kobayashi, H. J. Chem. Phys. 1993, 99, 4128-4139.
7. (b) Pasternack, R. F.; Schaefer, K. F.; Hambright, P. Inorg. Chem. 1994, 33, 2062-2065.
8. (a) Huang, C. Z.;L, Y. F.; Li, N.; Li, K. A.; Tong, S. Y. Bull. Chem. Soc. Jpn. 1998, 71, 1791-1797.
9. (b) Purrello, R.; Bellacchio, E.; Gurrieri, S.; Lauceri, R.; Raudino, A.; Scolaro, L. M.; Santori, A. M. J. Phys. Chem. B 1998, 102, 8852-8857.
10. Pasternack, R. F.; Gibbs, E. J.; Goudemer, A.; Antebi, A.; Bassner, S.; De Poy, L.; Yurner, D. H.; Williams, A.; Laplace, F.; Lansard, M. H.; Merienne, C.; Perrée-Fauvet, M. J. Am. Chem. Soc. 1985, 107, 8179-8186.
11. (b) Ito, A. S.; Azzellini, G. C.; Silva, S. C.; Serra, O.; Szabo, A. G. Biophys. Chem. 1992, 45, 79-89.
12. (c) Vergeldt, F. J.; Koehorst, R. B. M.; van Hoek, A.; Schaafsma, T. J. J. Phys. Chem. 1995, 99, 4397-4405.
13. (d) Iosif, A.; Grummt, U. W. J. Prakt. Chem./Chem.-Ztg. 1997, 339, 420-425.
14. Kano, K.; Minamizono, H.; Kitae, T.; Negi, S. J. Phys. Chem. 1997, 101, 6118-6124.
15. Kano, K.; Takei, M.; Hashimoto, S. J. Phys. Chem. 1990, 94, 2181-2187.
16. (a) Pasternack, R. F.; Bustamante, C.; Collings, P. J.; Giannetto, A.; Gibbs, E. J. J. Am. Chem. Soc. 1993, 115, 5393-5399.
17. (b) Mallamace, F.; Micali, N.; Seolaro, L. M.; Pasternack, R. F.; Romeo, A.; Terracina, A.; Trusso, S. J. Mol Struct. 1996, 383, 255-260.
18. (c) Micali, N.; Scolaro, L. M.; Romeo, A.; Mallamace, F. Physica A 1998, 249, 501-510.
19. Miller, K. J.; Savchik, J. A. J. Am. Chem. Soc. 1979, 101, 7206-7213.
20. (a) Hunter, C. A.; Lwighton, P.; Sanders, K. M. J. Chem. Soc., Perkin Trans. 1 1989, 547-552.
21. (b) Hunter, C. A.; Meah, M. N.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5773-5780.
22. (c) Anderson, H. L.; Hunter, C. A.; Meah, M. N.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5780-5789.
23. Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534.
24. Jorgensen, W. L.; Severance, D. L. J. Am. Chem. Soc. 1990, 112, 4768-4774.
25. (a) Kalyanasundaram, K. J Chem. Soc., Faraday Trans. 2 1983, 79, 1365-1374.
26. (b) Kalyanasundaram, K. J. Inorg. Chem. 1984, 23, 2453-2459.
27. (a) Ribo, J. M.; Crusats, J.; Ferrera, J.-A.; Valero, M. L. J. Chem. Soc., Chem. Commun. 1994, 681-682.
28. (b) Maiti, N. C.; Ravikanth, M.; Mazumdar, S.; Periasamy, N. J. Phys. Chem. 1995, 99, 17192-17197.
29. (c) Akins, D. L.; Zhu, H. R.; Guo, C. J. Phys. Chem. 1996, 100, 5420-5425.
30. (a) Jelley, E. E. Nature (London) 1936, 138, 1009-1010.
31. (b) Scheibe, G. Angew. Chem. 1936, 49, 563.
32. Fleischer, E. B.; Palmer, J. M.; Srivastava, T. S.; Chatterjee, A. J. Am. Chem. Soc. 1971, 93, 3162-3167.
33. Jin, R.-H.; Aoki, S.; Shima, K. J. Chem. Soc., Faraday Trans. 1997, 93, 3945-3953.
34. Zhang, Z.; Verma, A. L.; Nakashima, K.; Yoneyama, M.; Iriyama, K.; Ozaki, Y. Langmuir 1997, 13, 5726-5731.
35. (a) Pasternack, R. L.; Collings, P. J. Science 1995, 269, 935-939.
36. (b) de Paula, C. C.; Robblee, J. H.; Pasternack, R. F. Biophys. J. 1995, 68, 335-341.
37. Stone, A.; Fleischer, E. B. J. Am. Chem. Soc. 1968, 90, 2735-2748.
38. (a) Hamor, M. J.; Hamor, T. A.; Hoard, J. L. J. Am. Chem. Soc. 1964, 86, 1938-1942.
39. (b) Senge, M. O.; Medforth, C. J.; Forsyth, T. P.; Lee, D. A.; Olmstead, M. M.; Jentzen, W.; Pandey, R. K.; Shelnutt, J. A.; Smith, K. M. Inorg. Chem. 1997, 36, 1149-1163.
40. For example, see: (a) Fleischer, E. B.; Miller, C. K.; Webb, L. E. J. Am. Chem. Soc. 1964, 86, 2342-2347. (b) Senge, M. O.; Medforth, C. J.; Forsyth, T. P.; Lee, D. A.; Olmstead, M. M.; Jentzen, W.; Pandey, R. K.; Shelnutt, J. A.; Smith, K. M. Inorg. Chem. 1997, 36, 1149-1163.
41. For example, see: (a) Fleischer, E. B.; Miller, C. K.; Webb, L. E. J. Am. Chem. Soc. 1964, 86, 2342-2347. (b) Senge, M. O.; Medforth, C. J.; Forsyth, T. P.; Lee, D. A.; Olmstead, M. M.; Jentzen, W.; Pandey, R. K.; Shelnutt, J. A.; Smith, K. M. Inorg. Chem. 1997, 36, 1149-1163.
42. Tanford, C. The Hydrophbic Effect: Formation of Micelles and Biological Mambranes, 2nd ed.; John Wiley: New York, 1980.
43. Sinanoglu, O. In Molecular Associations in Biology; Pullman, B., Ed.; Academic: New York, 1968; pp 427-445.
44. Margalit, R.; Rotenberg, M. Biochem. J. 1984, 219, 445-450.
45. (a) Smithrud, D. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 339-343.
46. (b) Denti, T. Z. M.; van Gundteren, W. F.; Diederich, F. J. Am. Chem. Soc. 1996, 118, 6044-6051.
47. Satterlee, D. J.; Shelnutt, J. A. J. Phys. Chem. 1984, 88, 5487-5492.
48. Fur example, see: Breslow, D. In Structure and Reactivity in Aqueous Solution: Characterization of Chemical and Biological Systems: Cramer, C. J., Truhlar, D. G., Eds.; American Chemical Society: Washington. DC. 1994; Chapter 20.
49. (a) Onaka, M.; Shinoda, T.; Izumi, Y.; Nolen, E. Tetrahedron Lett. 1993, 34, 2625-2628.
50. (b) Onaka, M.; Shinoda, T.; Izumi, Y.; Nolen, E. Chem. Lett. 1993, 117-118.
51. (c) Shinoda, T.; Onaka, M.; Izumi, Y. Chem. Lett. 1995, 495-496.
52. Banfi, L.; Cabri, W.; Poli, G.; Potenza, D.; Scolastico, C. J. Org. Chem. 1987, 52, 5452-5457.
53. Schneider, H.-J.; Wang, M. J. Org. Chem. 1994, 59, 7473-7478.
54. Adler, A. D.; Longo, F. R.; Kampas, F.; Kim, J. J. Inorg. Nucl. Chem. 1970, 32, 2443-2445.
55. Sheldrick, G. M. In Cristallographic Computing 3; Sheldrick, G. M., Kruger, C., Goddard, R., Eds.; Oxford University Press: Oxford, 1985; pp 175-189.
56. Cromer, D. T.; Waber, J. T. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, U.K., 1974; Vol. 4.
57. Single-crystal structure analysis software, version 1.6, Molecular Structure Corp.: The Woodlands, TX 77381, 1993.