TD-DFT computational insight into the origin of wavelength-dependent E/Z photoisomerization of urocanic acid

Journal of Physical Chemistry A

Volumn 108, Issue 26, 2004, Pages 5662-5669

  Dmitrenko, Olga ^a   Reischl, Wolfgang ^b   Bach, Robert D ^a   Spanget Larsen, Jens ^c  

^a UNIVERSITY OF DELAWARE   (United States)

^b UNIVERSITY OF VIENNA   (Austria)

^c ROSKILDE UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION DYNAMICS; FLUORESCENCE SPECTRA; MOLECULAR ORBITALS; PHOTOISOMERIZATIONS;

CHEMICAL BONDS; CONFORMATIONS; ELECTRIC POTENTIAL; FLUORESCENCE; GROUND STATE; IRRADIATION; ISOMERIZATION;

ORGANIC ACIDS;

EID: 3142766198     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0499530     Document Type: Article

References (65)

1. (a) Mohammad, T.; Morrison, H.; HogenEsch, H. Photochem. Photobiol. 1999, 69, 115.
2. (b) Hug, D. H.; Hunter, J. K.; Dunkerson, D. D. J. Photochem. Photobiol., B 1998, 44, 117.
3. (c) Hanson, K. M.; Simon, J. D. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 10576.
4. (d) Haralampus-Grynaviski, N.; Ransom, C.; Ye, T.; Rozanowska, M.; Wrona, M.; Sarna, T.; Simon, J. D. J. Am. Chem. Soc. 2002, 124, 3461.
5. (e) Menon, E. L.; Morrison, H. Photochem. Photobiol. 2002, 75, 565.
6. (f) Schwartz, W.; Langer, K.; Schell, H.; Schonberger, A. Photodermatology 1986, 3, 239.
7. (a) Kammeyer, A. M.; Pavel, S.; Asghar, S. S.; Bos, J. D.; Teunissen, M. B. M. Photochem. Photobiol. 1997, 65, 593.
8. (b) Kinuta, M.; Yao, K.; Masuoka, N.; Ohta, J.; Teraoka, T.; Ubuka, T. Biochem. J. 1991, 275, 617.
9. (c) Norval, M.; El-Ghorr, A. A. Methods 2002, 28, 63.
10. (d) Vestey, J. P.; Norval, M. Photodermatol. Photoimmunol. Photomed. 1997, 13, 67.
11. (e) Norval, M. Photochem. Photobiol. 1996, 63, 386.
12. (f) Norval, M.; Gibbs, N. K.; Gilmour, J. Photochem. Photobiol. 1995, 62, 209.
13. (a) DeFabo, E. C.; Noonan, F. P. J. Exp. Med. 1983, 158, 84.
14. (b) Webber, L. J.; Wang, E.; DeFabo, E. C. Photochem. Photobiol. 1997, 66, 484.
15. (a) Morrison, H.; Bernasconi, C.; Pandey, G. Photochem. Photobiol. 1984, 40, 549.
16. (b) Morrison, H.; Avnir, D.; Bernasconi, C.; Fagan, G. Photochem. Photobiol. 1980, 32, 711.
17. (c) Hanson, K. M.; Li, B.; Simon, J. D. J. Am. Chem. Soc. 1997, 119, 2715.
18. (d) Li, B.; Hanson, K. M.; Simon, J. D. J. Phys. Chem. A 1997, 101, 969.
19. (e) Hanson, K. M.; Simon, J. D. Photochem. Photobiol. 1998, 67, 538.
20. (f) Hug, D. H.; Hunter, J. K. Photochem. Photobiol. 1994, 59, 303.
21. (a) Lewis, F. D.; Yoon, B. A. Res. Chem. Interned. 1995, 21, 749.
22. (b) Lewis, F. D.; Howard, D. K.; Oxman, J. D.; Upthagrove, A. L.; Quillen, S. L. J. Am. Chem. Soc. 1986, 108, 5964.
23. (c) Franceschi, S.; Sirieix, J.; Lauth-de Viguerie, N.; Riviere, M.; Lattes, A. C. R. Acad. Sci., Ser. IIc 1999, 2 (11), 299.
24. (a) Shukla, M. K.; Mishra, P. C. Spectrochim. Acta 1995, 51A (5), 831.
25. (b) Simon, J. D. Acc. Chem. Res. 2000, 33, 307 and references therein.
26. (a) Lahti, A.; Hotokka, M.; Neuvonen, K.; Ayras, P. J. Mol. Struct.: THEOCHEM 1995, 331, 169.
27. (b) Lahti, A.; Hotokka, M.; Neuvonen, K.; Ayras, P. Struct. Chem. 1997, 8, 331.
28. (c) Lahti, A.; Hotokka, M.; Neuvonen, K.; Karlstrom, G. Int. J. Quantum Chem. 1999, 72, 25.
29. (d) Lahti, A.; Hotokka, M.; Neuvonen, K.; Karlstrom, G. J. Mol. Struct.: THEOCHEM 1998, 452, 185.
30. (e) Laihia, J. K.; Lemmetyinen, H.; Fasanen, P.; Jansen, C. T. J. Photochem. Photobiol., B 1996, 33, 211.
31. (f) Page, C. S.; Merchan, M.; Serrano-Andres, L.; Olivucci, M. J. Phys. Chem. A 1999, 103, 9864.
32. (g) Page, C. S.; Olivucci, M.; Merchan, M. J. Phys. Chem. A 2000, 104, 8796.
33. (a) Danielsson, J.; Soderhall, J. A.; Laaksonen, A. Mol. Phys. 2002, 100, 1873.
34. (b) Danielsson, J.; Ulicny, J.; Laaksonen, A. J. Am. Chem. Soc. 2001, 123, 9817.
35. (c) Danielsson, J.; Laaksonen, A. Chem. Phys. Lett. 2003, 370, 625.
36. Ryan, W. L.; Levy, D. H. J. Am. Chem. Soc. 2001, 123, 961.
37. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
38. (a) Schlegel, H. B. J. Comput. Chem. 1982, 3, 214.
39. (b) Schlegel, H. B. Adv. Chem. Phys. 1987, 67 (Part 1), 249.
40. (c) Schlegel, H. B. In Modern Electronic Structure Theory; Yarkony, D. R., Ed.; World Scientific: Singapore, 1995; p 459.
41. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
42. (b) Lee, C.; Yang, W. and Parr, R. G. Phys. Rev. B 1988, 37, 785.
43. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
44. (b) Stevens, P. J.; Devlin, F. J.; Chabalowski, C. F. and Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
45. Barone, V.; Cossi, M.; Tomasi, J. J. Comput. Chem. 1998, 19, 404.
46. (a) Bauernschmitt, R.; Ahlrichs R. Chem. Phys. Lett. 1996, 256, 454.
47. (b) Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. J. Chem. Phys. 1998, 108, 4439.
48. (c) Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218.
49. (d) Stener, M.; Fronzoni, G.; Toffoli, D.; Decleva, P. Chem. Phys. 2002, 282, 337.
50. (e) Monat, J. E.; Rodriguez, J. H.; McCusker, J. K. J. Phys. Chem. A 2002, 106, 7399.
51. (a) NBO Version 3.1: Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F.
52. (b) Spanget-Larsen, J. J. Chem. Soc., Perkin Trans. 1985, 2, 417.
53. (c) Ridley, J. E.; Zerner, M. C. Theor. Chim. Acta 1973, 32, 111.
54. (d) HyperChem Molecular Modeling System. Release 5; Hypercube: Waterloo, Ontario, Canada, 1996.
55. (a) Dmitrenko, O.; Frederick, J. H.; Reischl, W. J. Photochem. Photobiol., A 2001, 139, 125.
56. (b) This approximation represents a crude means for estimating the width of the absorption profile, and it ignores the possibility that the bands may exhibit vibrational structure. Nevertheless, a more sophisticated treatment of the absorption band shape would require a significant effort to more fully characterize the excited state and is not justified given other approximations that are made in our treatment.
57. Brookman, J.; Chacón, J. N.; Sinclair, R. S Photochem. Photobiol. Sci. 2002, 1, 327.
58. Lawrence, M.; Marzzacco, C. J.; Morton, C.; Schwab, C.; Halpern, A. M. J. Phys. Chem. 1991, 95, 10294.
59. Lee, S.-I.; Jang, D.-J. J. Phys. Chem. 1995, 99, 7537.
60. Spanget-Larsen, J. J. Phys. Org. Chem. 1995, 8, 496.
61. (a) Waluk, J.; Rettig, W.; Spanget-Larsen, J. J. Phys. Chem. 1988, 92, 6930.
62. (b) Herbich, J.; Grabowski, Z. R.; Wojtowicz, H.; Golankievicz, K. J. Phys. Chem. 1989, 93, 3439.
63. (c) Sikorska, E.; Szymusiak, H.; Khmelinskii, I. V.; Koziolowa, A.; Spanget-Larsen, J.; Sikorski, M. J. Photochem. Photobiol., A 2003, 158, 45.
64. Balón, M.; Muñoz, M. A.; Carmona, C. Chem. Phys. 2004, 299, 67.
65. Sobolewski, A. L.; Domcke, W.; Dedonder-Lardeux, C.; Jouvet, C. Phys. Chem. Chem. Phys. 2002, 4, 1093.