Two-photon singlet oxygen sensitizers: Quantifying, modeling, and optimizing the two-photon absorption cross section

Journal of Physical Chemistry A

Volumn 105, Issue 51, 2001, Pages 11488-11495

  Poulsen, Tina D ^a   Frederiksen, Peter K ^a   Jørgensen, Mikkel ^b   Mikkelsen, Kurt V ^c   Ogilby, Peter R ^a  

^a AARHUS UNIVERSITY   (Denmark)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^c UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMOPHORES; LASER BEAMS; LIGHT ABSORPTION; PHOTONS;

TWO-PHOTON SINGLET OXYGEN SENSITIZERS;

OXYGEN;

EID: 0035961103     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp011974w     Document Type: Article

References (48)

1. Foote, C. S.; Clennan, E. L. In Active Oxygen in Chemistry, Foots, C. S., Valentine, J. S., Greenberg A., Liebman, J. F., Eds.; Chapman and Hall: London, 1995; pp 105-140.
2. Ogilby, P. R.; Kristiansen, M.; Mártire, D. O.; Scurlock, R. D.; Taylor, V. L.; Clough, R. L. Adv. Chem. Ser. 1996, 249, 113-126.
3. Singlet Oxygen; Frimer, A. A., Ed.; CRC Press: Boca Raton, 1985; Vol. I-IV.
4. Wilkinson, F.; Helman, W. P.; Ross, A. B. J. Phys. Chem. Ref. Data 1993, 22, 113-262.
5. Frederiksen, P. K.; Jørgensen, M.; Ogilby, P. R. J. Am. Chem. Soc. 2001, 123, 1215-1221.
6. McClain, W. M. Acc. Chem. Res. 1974, 7, 129-135.
7. Bhawalkar, J. D.; He, G. S.; Prasad, P. N. Rep. Prog. Phys. 1996, 59, 1041-1070.
8. Xu, C.; Webb, W. W. In Topics in Fluorescence Spectroscopy; Lakowicz, J., Ed.; Plenum Press: New York, 1997;
9. Vol. 5 Nonlinear and Two-Photon-Induced Fluorescence, pp 471-540.
10. Fisher, W. G.; Partridge, W. P.; Dees, C.; Wachter, E. A. Photochem. Photobiol. 1997, 66, 141-155.
11. Andersen, L. K.; Ogilby, P. R. Photochem. Photobiol. 2001, 73, 489-492.
12. Fuchs, J.; Thiele, J. Free Rad. Biol. Med. 1998, 24, 835-847.
13. Evleth, E. M.; Peticolas, W. L. J. Chem. Phys. 1964, 41, 1400-1407.
14. Birge, R. R.; Bennett, J. A.; Pierce, B. M.; Thomas, T. M. J. Am. Chem. Soc. 1978, 100, 1533-1539.
15. Birge, R. R.; Pierce, B. M. J. Chem. Phys. 1979, 70, 165-178.
16. Karna, S. P.; Prasad, P. N. J. Chem. Phys. 1991, 94, 1171-1181.
17. Lu, D.; Chen, G.; Perry, J. W.; Goddard, W. A. J. Am. Chem. Soc. 1994, 116, 10679-10685.
18. Chen, G.; Lu, D.; Goddard, W. A. J. Chem. Phys. 1994, 101, 5860-5864.
19. Barzoukas, M.; Blanchard-Desce, M. J. Chem. Phys. 2000, 113, 3951-3959.
20. Kogej, T.; Beljonne, D.; Meyers, F.; Perry, J. W.; Marder, S. R.; Brédas, J. L. Chem. Phys. Lett. 1998, 298, 1-6.
21. Albota, M.; Beljonne, D.; Brédas, 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.; Röckel, H.; Rumi, M.; Subramaniam, G.; Webb, W. W.; Wu, X.-L.; Xu, C. Science 1998, 281, 1653-1656.
22. Norman, P.; Luo, Y.; Ågren, H. Chem. Phys. Lett. 1998, 296, 8-18.
23. Norman, P.; Luo, Y.; Agren, H. J. Chem. Phys. 1999, 111, 7758-7765.
24. Luo, Y.; Norman, P.; Macak, P.; Ågren, H. J. Phys. Chem. A. 2000, 104, 4718-4722.
25. Wang, C.-K.; Macak, P.; Luo, Y.; Agren, H. J. Chem. Phys. 2001, 114, 9813-9820.
26. Sundholm, D.; Rizzo, A.; Jørgensen, P. J. Chem. Phys. 1994, 101, 4931-4935.
27. Hättig, C.; Christiansen, O.; Jorgensen, P. J. Chem. Phys. 1998, 108, 8355-8359.
28. Langhoff, S. R.; Davidson, E. R. J. Chem. Phys. 1976, 64, 4699-4710.
29. Olsen, J.; Jørgensen, P. J. Chem. Phys. 1985, 82, 3235-3264.
30. Jørgensen, M.; Krebs, F. C.; Bechgaard, K. J. Org. Chem. 2000, 65, 8783-8785.
31. Kennedy, G.; Perboni, A. D. Tetrahedron Lett. 1996, 37, 7611-7614.
32. Helgaker, T.; Jensen, H. J. A.; Jørgensen, P.; Olsen, J.; Ruud, K.; Ågren, H.; Bak, K. L.; Bakken, V.; Christiansen, O.; Dahle, P.; Dalskov, E. K.; Enevoldsen, T.; Fernandez, B.; Heiberg, H.; Hettema, H.; Jonsson, D.; Kirpekar, S.; Kobayashi, R.; Koch, H.; Mikkelsen, K. V.; Norman, P.; Packer, M. J.; Ruden, T. A.; Saue, T.; Sauer, S. P. A.; Sylvester-Hvid, K. O.; Taylor, P. R.; Vahtras, O. Dalton, an ab initio electronic structure program, Release 1.1 (July 2000). See http://www.kjemi.uio.no/software/ dalton/dalton.html
33. Shen, Y. R. The Principles of Nonlinear Optics; Wiley: New York, 1984.
34. McClain, W. M. J. Chem. Phys. 1971, 55, 2789-2796.
35. Frisch, M. J.; Trucks, W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrezewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Daprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Baraone, V.; Cossi, M.; Cammi, R.; Menucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Peterson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Cioslowski, J. B. F.; Ortiz, J. V.; Stefanov, B. B.; Jiu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. I.; Keith, T.; Al-Laham, M. A.; Peng, C.-Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M.; Andres, J. L.; Head-Gordon, M.; Repolgle, E. S.; Pople, J. A. Caussian 98; Gaussian Inc.: Pittsburgh, PA, 1998.
36. Peticolas, W. L. Annu. Rev. Phys. Chem. 1967, 18, 233-260.
37. Mikkelsen, K. V.; Luo, Y.; Ågren, H.; Jørgensen, P. J. Chem. Phys. 1995, 102, 9362-9367.
38. Sylvester-Hvid, K. O.; Mikkelsen, K. V.; Jonsson, D.; Norman, P.; Ågren, H. J. Chem. Phys. 1998, 109, 5576-5584.
39. Rumi, M.; Ehrlich, J. E.; Heikal, A. A.; Perry, J. W.: Barlow, S.; Hu, Z.; McCord-Maughon, D.; Parker, T. C.; Röckel, H.; Thayumanavan, S.; Marder, S. R.; Beljonne, D.; Brédas, J.-L. J. Am. Chem. Soc. 2000, 122, 9500-9510.
40. Pati, S. K.; Marks, T. J.; Ratner, M. A. J. Am. Chem. Soc. 2001, 123, 7287-7291.
41. Meyers, F.; Marder, S. R.; Pierce, B. M.; Brédas, J.-L. J. Am. Chem. Soc. 1994, 116, 10703-10714.
42. Jensen, F. Introduction to Computational Chemistry, John Wiley and Sons: Chichester, 1999.
43. Hehre, W. J.; Radom, L.; Pople, J. A.; Schleyer, P. v. R. Ab Initio Molecular Orbital Theory, Wiley: New York, 1986.
44. Wang, C.-K.; Macak, P.; Luo, Y.; Agren, H., private communication.
45. With respect to the plane of the central ring in the three ring system of 5(H), (1) the planes of the bridging ethylene units define dihedral angles of 20°, twisted in opposite directions to maintain the center of inversion in the molecule, and (2) the planes of the outer rings define dihedral angles of 5°, again twisted such as to maintain the inversion center. A corollary of the preceding is that the planes of the outer rings and the bridging ethylene units define an angle of 15°.
46. Dam, N.; Scurlock, R. D.; Wang, B.; Ma, L.; Sundahl, M.; Ogilby, P. R. Chem. Mater. 1999, 11, 1302-1305.
47. Redmond, R. W.; Braslavsky, S. E. Chem. Phys. Lett. 1988, 148, 523-529.
48. Kershaw, S. In Characterization Techniques and Tabulations for Organic Nonlinear Optical Materials; Kuzyk, M. G., Dirk, C. W., Eds.; Marcel Dekker: New York, 1998; pp 515-654.