Photoproduct selectivity in reactions involving singlet and triplet excited states within bile salt micelles

Langmuir

Volumn 22, Issue 5, 2006, Pages 2185-2192

  Pattabiraman, Mahesh ^a   Kaanumalle, Lakshmi S ^a   Ramamurthy, V ^a  

^a Department of Biology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BILE SALT MICELLES; ISOTROPIC SOLUTIONS; RADICAL PAIRS;

CHEMICAL BONDS; MICELLES; SALTS;

PHOTOCHEMICAL REACTIONS;

EID: 33644917979     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la0528192     Document Type: Article

References (58)

1. Natarajan, A.; Kaanumalle, L. S.; Ramamurthy, V. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W., Lenci, F., Eds.; CRC Press: Boca Raton, FL, 2004; Vol. 3, p 107.
2. Kaanumalle, L. S.; Natarajan, A.; Ramamurthy, V. In Synthetic Organic Photochemistry; Griesbeck, A., Mattay, J., Eds.; Marcel Dekker: New York, 2004; Vol. 9, p 553.
3. (a) Ramamurthy, V.; Eaton, D. F. Acc. Chem. Res. 1988, 21, 300.
4. (b) Weiss, R. G.; Ramamurthy, V.; Hammond, G. S. Acc. Chem. Res. 1993, 26, 530.
5. (c) Ramamurthy, V.; Weiss, R. G.; Hammond, G. S. In Advances in Photochemistry; Volman, D. H., Neckers, D., Hammond, G. S., Eds.; Wiley-Interscience: New York, 1993; Vol. 18, p 67.
6. (d) Scaiano, J. C.; Garcia, H. Acc. Chem. Res. 1999, 32, 783.
7. (e) Turro, N. J. Acc. Chem. Res. 2000, 33, 637.
8. (f) Tung, C.-H.; Wu, L.-Z.; Zhang, L.-P.; Li. H.-R.; Yi, X.-Y.; Song, K.; Xu, M.; Yuan, Z.-Y.; Guan, J.-Q.; Wang, H.-W.; Ying, Y.-M.; Xu, X.-H. Pure Appl. Chem. 2000, 72, 2289.
9. (g) Bhattacharya, K. Acc. Chem. Res. 2003, 36, 95.
10. (h) Tung, C.-H.; Wu, L.-Z.; Zhang, L.-P.; Chen, B. Acc. Chem. Res. 2003, 36, 39.
11. (i) Liu, R. S. H.; Hammond, G. S. Acc. Chem. Res. 2005, 38, 396.
12. (j) Huang, C.-H.; Bassani, D. M. Eur. J. Org. Chem. 2005, 19, 4041.
13. (a) Kaanumalle, L. S.; Nithyanandhan, J.; Pattabiraman, M.; Jayaraman, N.; Ramamurthy, V. J. Am. Chem. Soc. 2004, 126, 8999.
14. (b) Kaanumalle, L. S.; Ramesh, R.; Maddipatla, M. V. S. N.; Nithyanandhan, J.; Jayaraman, N.; Ramamurthy, V. J. Org. Chem. 2005, 70, 5062.
15. (c) Kaanumalle, L. S.; Gibb, C. L. D.; Gibb, B. C.; Ramamurthy, V. J. Am. Chem. Soc. 2005, 127, 3674.
16. (d) Kaanumalle, L. S.; Gibb, C. L. D.; Gibb, B. C.; Ramamurthy, V. J. Am. Chem. Soc. 2004, 126, 14366.
17. (e) Arumugam, S.; Vutukuri, D. R.; Thayumanavan, S.; Ramamurthy, V. J. Am. Chem. Soc. 2005, 127, 13200.
18. (f) Karthikeyan, S.; Ramamurthy, V. Tetrahedron Lett. 2005, 46, 4495.
19. (g) Pattabiraman, M.; Natarajan, A.; Kaanumalle, L. S.; Ramamurthy, V. Org. Lett. 2005, 7, 529.
20. (h) Pattabiraman, M.; Natarajan, A.; Kaliappan, R.; Mague, J. T.; Ramamurthy, V. Chem. Commun. 2005, 4542.
21. (i) Kaliappan, R.; Kaanumalle, L. S.; Ramamurthy, V. Chem. Commun. 2005, 4056.
22. (a) Xiaohong, C.; David, G. J. W.; Wiedmann, S.; Timothy, S. J. Pharmcol. Sci. 1997, 86, 372.
23. (b) Beckerdite, J. M.; Adams, E. T. Biophys. Chem. 1985, 21, 103.
24. Hofmann, A. F. Biochem. J. 1963, 89, 57.
25. (a) Mukerjee, P.; Moroi, Y.; Murata, M.; Yang, A. Y. S. Hepatology 1984, 4, 61.
26. (b) Mukerjee, P.; Cardinal, J. R. J. Pharm. Sci. 1976, 65, 882.
27. (c) Ekwall, P. J. Colloid Sci. 1954, (Suppl. 1), 66.
28. (a) Small, D. M. In The Bile Salts; Nair, P. P., Kritchevsky, D., Eds.; Plenum Press: New York, 1971; Vol. 1, p 249.
29. (b) Li, G.; McGown, L. B. J. Phys. Chem. 1993, 97, 6745.
30. (a) Esposito, G.; Giglio, E.; Pavel, N. V.; Zanobi, A. J. Phys. Chem. 1987, 91, 356.
31. (b) O'Connor, C. J.; Wallace, R. G. Adv. Colloid Interface Sci. 1985, 22, 1.
32. (c) Shurtenberger, P.; Mazer, N.; Kanzig, W. J. Phys. Chem. 1983, 87, 308.
33. Small, D. M.; Penkett, S. A.; Chapman, D. Biochim. Biophys. Acta 1969, 176, 178.
34. (a) Meyerhoffer, S. M.; McGown, L. B. Anal. Chem. 1991, 63, 2082.
35. (b) Zana, R.; Guveli, D. J. Phys. Chem. 1985, 89, 1687.
36. (c) Lindman, B.; Kamenka, N.; Fahre, H.; Uimus, J.; Weiloch, T. J. Colloid Interface Sci. 1980, 556.
37. (a) Rinco, O.; Christine, N. M.; Ovans, R.; Bohne, C. Photochem. Photobiol. 2003, 2, 1140.
38. (b) Rinco, O.; Kleinman, M. H.; Bohne, C. Langmuir 2001, 17, 5781.
39. (c) Li, Y.; Holzwarth, J. F.; Bohne, C. Langmuir 2000, 16, 2038.
40. (d) Ju, C.; Bohne, C. Photochem. Photobiol. 1996, 63, 60.
41. (e) Ju, C.; Bohne, C. J. Phys. Chem. 1996, 100, 3847.
42. (f) Gouin, S.; Zhu, X. X. Langmuir 1998, 14, 4025.
43. Small, D. M. Adv. Chem. Ser. 1968, 84, 31.
44. (a) Pitchumani, K.; Warrier, M.; Cui, C.; Weiss, R. O.; Ramamurthy, V. Tetrahedron Lett. 1996, 37, 6251.
45. (b) Miranda, M. A. In CRC Handbook of Photochemistry and Photobiology, Horspool, W. M., Song, P. S.; Eds.; CRC Press: Boca Raton, 1995; p 570.
46. (c) Cui, C.; Weiss, R. G. J. Am. Chem. Soc. 1993, 115, 9820.
47. (a) Zhang, S.-Z.; Xie, J.-W.; Liu, C.-S. Anal. Chem. 2003, 75, 91.
48. (b) Sugihara, G.; Yamakawa, K.; Murata, Y.; Tanaka, M. J. Phys. Chem. 1982, 86, 2784.
49. (c) Fischer, L.; Oakenfull, D. Aust. J. Chem. 1979, 32, 31.
50. (a) Zhang, Z.; Turro, N. J.; Johnston, L.; Ramamurthy, V. Tetrahedron Lett. 1996, 37, 4861.
51. (b) Turro, N. J.; Gould, I. R.; Baretz, H. B. J. Phys. Chem. 1983, 87, 531.
52. (c) Lunazzi, L.; Ingold, K. U.; Scaiano, J. C. J. Phys. Chem. 1983, 87, 529.
53. (a) Robbins, W. K.; Eastman, R. H. J. Am. Chem. Soc. 1970, 92, 6076.
54. (b) Engel, P. S. J. Am. Chem. Soc. 1970, 92, 6074.
55. Turro, N. J.; Weed, G. C. J. Am. Chem. Soc. 1983, 105, 1861.
56. (a) Lewis, F. D.; Lauterbach, R. T.; Heine, H.-G.; Hartmann, W.; Rudolph, H. J. Am. Chem. Soc. 1975, 97, 1519.
57. (b) Heine, H.-G. Tetrahedron Lett. 1972, 47, 4755.
58. Devanathan, S.; Ramamurthy, V. J. Phys. Org. Chem, 1988, 1, 91.