Single- and two-photon properties of a dye-derivatized roussin's red salt ester (Fe2(μ-RS)2(NO)4) with a large TPA cross section

Inorganic Chemistry

Volumn 46, Issue 2, 2007, Pages 395-402

  Wecksler, Stephen R ^a   Mikhailovsky, Alexander ^a   Korystov, Dmitry ^a   Buller, Fabian ^a   Kannan, Ramamurthi ^b   Tan, Loon Seng ^b   Ford, Peter C ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b AIR FORCE RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; IRON DERIVATIVE; NITRIC OXIDE; ROUSSIN'S RED SALT; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; FLUORESCENCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; PHOTON;

ESTERS; FLUORESCENCE; IRON COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; NITRIC OXIDE; PHOTOCHEMISTRY; PHOTONS;

EID: 33846593429     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic0607336     Document Type: Article

References (82)

1. Taken in part from the Ph.D. dissertation of S. R. Wecksler, University of California, Santa Barbara, 2006.
2. Visiting undergraduate researcher from the University of Muenster, Germany.
3. (a) Ignarro, L. J.; Buga, G. M.; Wood, K. S.; Byrns, R. E.; Chaudhuri, G. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 9265.
4. (b) Vasodilation: Vascular Smooth Muscle, Peptides, Autonomic Nerves and Endothelium; Furchgott, R. F., Ed.; Raven Press: New York, 1988.
5. (c) Palmer, R. M. J.; Ferrige, A. G.; Moncada, S. Nature 1987, 327, 524.
6. (d) Palmer, R. M. J.; Ashton, D. S.; Moncada, S. Nature (London) 1988, 333, 664-666.
7. (e) Azuma, H.; Ishikawa, M.; Sekizaki, S. Br. J. Pharmacol. 1986, 88, 411-415.
8. (f) Radomski, M. W.; Palmer, R. M. J.; Moncada, S. Br. J. Pharmacol. 1987, 92, 181-187.
9. (g) Steuhr, D. J.; Marietta, M. A. J. Immunol. 1987, 139, 518-525.
10. (h) Iyengar, R.; Stuehr, D. J.; Marietta, M. A. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 6369-6373.
11. (i) Nitric Oxide: Biology and Pathobiology; Ignarro, L. J., Ed.; Academic Press: San Diego, 2000.
12. (a) Howard-Flanders, P. Nature (London) 1957, 180, 1191.
13. (b) Thomlinson, R. H.; Gray, L. H. Br. J. Cancer 1995, 9, 539-549.
14. (c) Powers, W. E.; Tolmach, L. J. Nature (London) 1963, 197, 710-711.
15. (d) Mitchell, J. B.; Wink, D. A.; DeGraff, W.; Gamson, J.; Keefer, L. K.; Krishna, M. C. Cancer Res. 1993, 53, 5845-5848.
16. (a) Fung, H.-L. Annu. Rev. Pharmacol. Toxicol. 2004, 44, 67-85.
17. (b) Katsuki, S.; Arnold, W. P.; Murad, F. J. Cyclic Nucleotide Res. 1977, 3, 239-247.
18. (c) Marsh, N.; Marsh, A. Clin. Exp. Pharmacol. Physiol. 2000, 27, 313-319.
19. (d) Cena, C.; Lolli, M. L.; Lazzarato, L.; Guaita, E.; Morini, G.; Coruzzi, G.; McElroy, S. P.; Megson, I. L.; Fruttero, R.; Gasco, A. J. Med. Chem. 2003, 46, 747-754.
20. (a) Ford, P. C.; Bourassa, J.; Miranda, K. M.; Lee, B.; Lorkovic, I.; Boggs, S.; Kudo, S.; Laverman, L. Coord. Chem. Rev. 1998, 171, 185-202.
21. (b) Pavlos, C. M.; Xu, H.; Toscano, J. P. Curr. Top. Med. Chem. 2005, 5, 635-645.
22. (a) Hoshino, M.; Ozawa, K.; Seki, H.; Ford, P. C. J. Am. Chem. Soc. 1993, 115, 9568-9575.
23. (b) Lorkovic, I. M.; Miranda, K. M.; Lee, B.; Bernhard, S.; Schoonover, J. R.; Ford, P. C. J. Am. Chem. Soc. 1998, 120, 11674-11683.
24. (c) Laverman, L.; Ford, P. C. J. Am. Chem. Soc. 2001, 123, 11614-11622.
25. (d) Joseph, C.; Ford, P. C. J. Am. Chem. Soc. 2005, 127, 6737-6743.
26. (a) Works, C. F.; Ford, P. C. J. Am. Chem. Soc. 2000, 122, 7592-7593.
27. (b) Works, C. F.; Jocher, C. J.; Bart, G. D.; Bu, X.; Ford, P. C. Inorg. Chem. 2002, 41, 3728-3739.
28. (a) De Leo, M.; Ford, P. C. J. Am. Chem. Soc. 1999, 121, 1980-1981.
29. (b) De Leo, M.; Ford, P. C. Coord. Chem. Rev. 2000, 208, 47-59.
30. (c) DeRosa, F.; Bu, X.; Ford, P. C. Inorg. Chem. 2005, 44, 4157-4165.
31. (d) DeRosa, F.; Bu, X.; Pohaku, K.; Ford, P. C. Inorg. Chem. 2005, 44, 4166-4174.
32. (a) Bourassa, J.; DeGraff, W.; Kudo, S.; Wink, D. A.; Mitchell, J. B.; Ford, P. C. J. Am. Chem. Soc. 1997, 119, 2853-2860.
33. (b) Bourassa, J.; Lee, B.; Bernard, S.; Schoonover, J.; Ford, P. C. Inorg. Chem. 1999, 38, 2947-2952.
34. (c) Bourassa, J.; Ford, P. C. Coord. Chem. Rev. 2000, 200-202, 887-900.
35. (a) Dougherty, T. J.; Marcus, S. L. Eur. J. Cancer 1992, 28A, 1734-1742.
36. (b) Master, B. R.; So, P. T.; Gratton, E. Biophys. J. 1997, 72, 2405-2412.
37. (a) Denk, W.; Strickler, J. H.; Webb, W. W. Science 1990, 248, 73-76.
38. (b) König, K. J. Microsc. (Oxford) 2000, 200, 83-104.
39. (b) So, P. T. C.; Dong, C. Y.; Masters, B. R.; Berland, K. M. Annu. Rev. Biomed. Eng. 2000, 2, 399-429.
40. (c) Zhou, W.; Kuebler, S. M.; Braun, K. L.; Yu, T.; Cammack, J. K.; Ober, C. K.; Perry, J. W.; Marder, S. R. Science 2002, 296, 1106-9.
41. (a) Dougherty, T. J.; Kaufman, J. E.; Goldbarb, A.; Weishaupt, K. R.; Boyle, D.; Mittleman, A. Cancer Res. 1978, 38, 2628.
42. (b) Bodaness, R. S.; Heller, D. F.; Krasinski, J.; King, D. S. J. Biol. Chem. 1986, 261, 12098-12101.
43. (c) Fischer, W. G.; Partridge, W. P., Jr.; Dees, C.; Wachter, E. A. Photochem. Photobiol. 1997, 66, 141-155.
44. (d) Bhawalkar, J. D.; Kumar, N. D.; Zhao, C.-F.; Prasad, P. N. J. Clin. Lasers Med. Surg. 1997, 15, 201-204.
45. (e) Jaconi, M.; Pyle, J.; Bortolon, R.; Ou, J.; Clapham, D. Curr. Biol. 1997, 7, 599-602.
46. (f) Lipp, P.; Niggli, E. J. Physiol. 1998, 508, 801-809.
47. (g) Brown, E. B.; Webb, W. W. Methods Enzymol. 1998, 291, 356-380.
48. (h) Furuta, T.; Wang, S. S.; Dantzker, J. L.; Dore, T. M.; Bybee, W. J.; Callaway, E. M.; Denk, W.; Tsien, R. Y. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 1193-1200.
49. (i) Frederiksen, P. K.; Jørgensen, M.; Ogilby, P. R. J. Am. Chem. Soc. 2001, 123, 1215-1221.
50. (j) Dichtel, W. R.; Serin, J. M.; Edder, C.; Fréchet, J. M. J.; Matuszewski, M.; Tan, L.-S.; Ohulchanskyy, T. Y.; Prasad, P. N. J. Am. Chem. Soc. 2004, 126, 5380-5381.
51. (k) Nikolenko, V.; Yuste, R.; Zayat, L.; Baraldo, L. M.; Etchenique, R. Chem. Commun. 2005, 1752-1754.
52. Conrado, C. L.; Bourassa, J.; Egler, C.; Wecklser, S.; Ford, P. C. Inorg. Chem. 2003, 42, 2288-2293.
53. Conrado, C. L.; Wecksler, S.; Egler, C.; Magde, D.; Ford, P. C. Inorg. Chem. 2004, 43, 5543-5549.
54. Wecksler, S. R.; Mikhailovsky, A.; Ford, P. C. J. Am. Chem. Soc. 2004, 126, 13566-13567.
55. Wecksler, S. R.; Hutchinson, J.; Ford, P. C. Inorg. Chem. 2006, 45, 1192-1200.
56. Wecksler, S. R.; Mikhailovsky, A.; Korystov, D.; Ford, P. C. J. Am. Chem. Soc. 2006, 128, 3831-3837.
57. (a) Roussin, F. Z. Ann. Chim. Phys. 1858, 52, 285.
58. (b) Butler, A. R.; Glidewell, C.; Li, M.-H. Adv. Inorg. Chem. 1988, 32, 335-393.
59. Goyan, R. L.; Cramb, D. T. Photochem. Photobiol. 2000, 72, 821-827.
60. Webb, W. W.; Xu, C. J. Opt. Soc. Am. B 1997, 13, 481-491.
61. (a) Meyers, F.; Marder, S. R.; Pierce, B. M.; Brédas, J.-L. J. Am. Chem. Soc. 1994, 116, 10703-10714.
62. (b) Baur, J. W.; Alexander, M. D., Jr.; Banach, M.; Denny, L. R.; Reinhardt, B. A.; Vaia, R. A. Chem. Mater. 1999, 11, 2899-2906.
63. (c) Marder, S. R.; Gorman, C. B.; Meyers, F.; Perry, J. W.; Bourhill, G.; Brédas, J.-L.; Pierce, B. M. Science 1994, 265, 632-635.
64. (d) Woo, H. Y.; Hong, J. W.; Mikhailovsky, A.; Korystov, D.; Bazan, G. C. J. Am. Chem. Soc. 2005, 127, 820-821.
65. (e) Kim, D. Y.; Ahn, T. K.; Kwon, J. H.; Kim, D.; Ikeue, T.; Aratani, N.; Osuka, A.; Shigeiwa, M.; Maeda, S. J. Phys. Chem. A 2005, 109, 2996-2999.
66. (f) Rumi, M.; Ehrlich, J. E.; Heikal, A. A.; Perry, J. W.; Barlow, S.; Hu, Z.; McCord-Maughon, D.; Parker, C. T.; Rockel, H.; Thayumanavan, S.; Marder, S. R.; Beljonne, D.; Brédas, J.-L. J. Am. Chem. Soc. 2000, 122, 9500-9510.
67. (g) Belfield, K. D.; Morales, A. R.; Kang, B.-S.; Hales, J. M.; Hagan, D. J.; Van Stryland, E. W.; Chapela, V. M.; Percino, J. Chem. Mater. 2004, 16, 4634-4641.
68. (h) Katan, C.; Terenziani, F.; Mongin, O.; Werts, M. H. V.; Porres, L.; Pons, T.; Mertz, J.; Tretiak, S.; Blanchard-Desce, M. J. Phys. Chem. A 2005, 109, 3024-3037.
69. (i) Drobizhev, M.; Karotki, A.; Dzenis, Y.; Rebane, A.; Suo, Z.; Spangler, C. W. J. Phys. Chem. B 2003, 107, 7540-7543.
70. Albota, M.; Beljonne, D.; Bredas, J. L.; Ehrlich, J. E.; Fu, J. Y.; Heikal, A. A.; Hess, S. E.; Kogej, T.; Levin, M. D.; Marder, S. R.; McCord-Maughon, D.; Perry, J. W.; Rockel, H.; Rumi, M.; Subramaniam, G.; Webb, W. W.; Wu, X. L.; Xu, C. Science 1988, 281, 1653-1656.
71. (a) Tan, L.-S.; Kannan, R.; Matuszewski, M. J.; Khur, I. J.; Feld, W. A.; Dang, T. D.; Dombroskie, A. G.; Vaia, R. A.; Clarson, S. J.; He, G. S.; Lin, T.-C.; Prasad, P. N. Proc. SPIE - Int. Soc. Opt. Eng. 2003, 4797, 171-178.
72. (b) He, G. S.; Lin, T.-C.; Dai, J.; Prasad, P. N.; Kannan, R.; Dombroskie, A. G.; Vaia, R. A.; Tan, L.-S. J. Chem. Phys. 2004, 120, 5275-5284. It should be pointed out that inherent in the nonlinear absorption (transmission) measurement using either nanosecond or picosecond laser pulses is the assumption that the two-photon process is the predominant mechanism responsible for the observed intensity-dependent nonlinear absorption. However, it is now well recognized that the strong TPA process increases molecular populations considerably in excited states, and thus a secondary process, i.e., the cascaded one-photon absorption from the excited states, may greatly enhance the observed nonlinear absorption of the input laser beam. Since it is difficult to separate these two contributions through the nonlinear absorption measurement in these time regimes, the term "effective TPA cross section" is used to describe the apparent δ values under these excitation conditions for the two-photon chromophore. The effective cross section of a TPA chromophore can be more than 2 orders of magnitude larger than the intrinsic cross section obtained via a femtosecond masurement, depending on the type of technique (transmission or fluorescence method) used.
73. (a) Rogers, J. E.; Slagle, J. E.; McLean, D. G.; Sutherland, R. L.; Sankaran, B.; Kannan, R.; Tan, L.-S.; Fleitz, P. A. J. Phys. Chem. A 2004, 108, 5514-5520.
74. (b) Sutherland, R. L.; Brant, M. C.; Heinrichs, J.; Rogers, J. E.; Slagle, J. E.; McLean, D. G.; Fleitz, P. A. J. Opt. Soc. Am. B 2005, 22, 1939-1948.
75. Sjöback, R.; Nygren, J.; Kubista, M. Spectrochim. Acta, Part A 1995, 51, L7-L21.
76. (a) Calvert, J.; Pitts, J. Photochemistry; Wiley & Sons: New York, 1967.
77. (b) Hatchard, C.; Parker, C. Proc. R. Soc. London, Ser. A 1956, 255, 518.
78. (a) Shen, Y. R. The Principles of Non-linear Optics; Wiley: New York, 1984.
79. (b) Lin, S. H.; Fujimura, Y. F.; Neusser, H. J.; Schlag, E. W. Multiphoton Spectroscopy of Molecules; Academic Press: Orlando, FL, 1984.
80. (c) Prasad, P. N.; Williams, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; Wiley: New York, 1991.
81. (a) Wink, D. A.; Derbyshire, J. F.; Nims, R. W.; Saavedra, J. E.; Ford, P. C. Chem. Res. Toxicol. 1993, 6, 23.
82. (b) Kudo, S.; Bourassa, J. L.; Boggs, S. E.; Sato, Y.; Ford, P. C. Anal. Biochem. 1997, 247, 193-202.