Bridged photochromic diarylethenes investigated by ultrafast absorption spectroscopy: Evidence for two distinct photocyclization pathways

Journal of the American Chemical Society

Volumn 132, Issue 21, 2010, Pages 7379-7390

  Aloïse, Stéphane ^a   Sliwa, Michel ^a   Pawlowska, Zuzanna ^a   Réhault, Julien ^a   Dubois, Julien ^a   Poizat, Olivier ^a   Buntinx, Guy ^a   Perrier, Aurélie ^b   Maurel, François ^b   Yamaguchi, Shouhei ^c   Takeshita, Michinori ^c  

^a CNRS   (France)

^b UNIVERSITÉ PARIS DIDEROT   (France)

^c SAGA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BISTABLES; CONICAL INTERSECTION; CORRELATION DIAGRAMS; DFT CALCULATION; EXCITATION WAVELENGTH; FEMTOSECOND TRANSIENT SPECTROSCOPY; INTERNAL CONVERSIONS; NON-POLAR SOLVENTS; PHOTOCHEMICAL PATHWAYS; PHOTOCHROMIC DIARYLETHENES; PHOTOCYCLIZATION; PHOTOCYLIZATION; POLAR SOLVENTS; POLARITY EFFECT; SINGLET STATE; SOLVENT POLARITY; STRUCTURAL EFFECT; TRANSIENT STATE; ULTRA-FAST; VERTICAL EXCITATION; VIBRATIONAL COOLING;

GROUND STATE; OLEFINS; PHOTOCHROMISM; QUANTUM THEORY; REACTION KINETICS; SOLVENTS; SULFUR COMPOUNDS;

ABSORPTION SPECTROSCOPY;

CARBON; CYCLOPHANE DERIVATIVE; ETHYLENE; SOLVENT;

ABSORPTION SPECTROSCOPY; ARTICLE; CASE REPORT; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CYCLIZATION; DENSITY FUNCTIONAL THEORY; HUMAN; PHOTOCHEMISTRY;

EID: 77952855557     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja910813x     Document Type: Article

References (53)

1. Bouas-Laurent, H. and Dürr, H. Photochromism; Elsevier Science B.V.: Amsterdam, 2003.
2. Irie, M. Chem. Rev. 2000, 100, 1685
3. Tsuboi, Y., Shimizu, R., Shoji, T., and Kitamura, N. J. Am. Chem. Soc. 2009, 131, 12623
4. Al-Atar, U., Fernandes, R., Johnsen, B., Baillie, D., and Branda, N. R. J. Am. Chem. Soc. 2009, 131, 15966
5. Morimoto, M., Miyasaka, H., Yamashita, M., and Irie, M. J. Am. Chem. Soc. 2009, 131, 9823
6. Wing-Wah Yam, V., Ka-Wai Lee, J., Ko, C. C., and Nianyong, Z. J. Am. Chem. Soc. 2009, 131, 912
7. Takeshita, M. and Yamato, T. Tetrahedron Lett. 2001, 42, 4345
8. Takeshita, M., Inoue, M., Hisasue, H., Maekawa, S., and Nakamura, T. J. Phys. Org. Chem. 2007, 20, 830
9. Tamai, N., Saika, T., Shimidzu, T., and Irie, M. J. Phys. Chem. 1996, 100, 4689
10. Owrutsky, J. C., Nelson, H. H., Baronavski, A. P., Kim, O. K., Tsivgoulis, G. M., Gilat, S. L., and Lehn, J.-M. Chem. Phys. Lett. 1998, 293, 555
11. Hania, P. R., Telesca, R., Lucas, L. N., Pugzlys, A., Van Esch, J. H., Feringa, B. L., Snijders, J. G., and Duppen, K. J. Phys. Chem. A 2002, 106, 8498
12. Hania, P. R., Pugzlys, A., Lucas, L. N., De Jong, J. J. D., Telesca, R., Feringa, B. L., Van Esch, J. H., and Duppen, K. J. Phys. Chem. A 2005, 109, 9437
13. Miyasaka, H., Nobuto, T., Itaya, A., Tamai, N., and Irie, M. Chem. Phys. Lett. 1997, 269, 281
14. Miyasaka, H., Nobuto, T., Murakami, M., Itaya, A., Tamai, N., and Irie, M. J. Phys. Chem. A 2002, 106, 8096
15. Okabe, C., Nakabayashi, T., Nishi, N., Fukaminato, T., Kawai, T., Irie, M., and Sekiya, H. J. Phys. Chem. A 2003, 107, 5384
16. Shim, S., Eom, I., Joo, T., Kim, E., and Kim, K. S. J. Phys. Chem. A 2007, 111, 8096
17. Ern, J., Bens, A. T., Martin, H.-D., Mukamel, S., Schmid, D., Tretiak, S., Tsiper, E., and Kryschi, C. J. Lumin. 2000, 87-89, 742
18. Ern, J., Bens, A. T., Bock, A., Martin, H.-D., and Kryschi, C. J. Lumin. 1998, 76-77, 90
19. Ern, J., Bens, A. T., Martin, H.-D., Mukamel, S., Schmid, D., Tretiak, S., Tsiper, E., and Kryschi, C. Chem. Phys. 1999, 246, 115
20. Shim, S., Joo, T., Bae, S. C., Kim, K. S., and Kim, E. J. Phys. Chem. A 2003, 107, 8106
21. Bens, A. T., Ern, J., Kuldova, K., Trommsdorff, H. P., and Kryschi, C. J. Lumin. 2001, 94-95, 51
22. Nakamura, S. and Irie, M. J. Org. Chem. 1988, 53, 6136
23. Boggio-Pasqua, M., Ravaglia, M., Bearpark, M. J., Garavelli, M., and Robb, M. A. J. Phys. Chem. A 2003, 107, 11139
24. Asano, Y., Murakami, A., Kobayashi, T., Goldberg, A., Guillaumont, D., Yabushita, S., Irie, M., and Nakamura, S. J. Am. Chem. Soc. 2004, 126, 12112
25. Nakamura, S., Kobayashi, T., Takata, A., Uchida, K., Asano, Y., Murakami, A., Goldberg, A., Guillaumont, D., Yokojima, S., Koatake, S., and Irie, M. J. Phys. Org. Chem. 2007, 20, 821
26. Uchida, K., Guillaumont, D., Tsuchida, E., Mochizuki, G., Irie, M., Murakami, A., and Nakamura, S. THEOCHEM 2002, 579, 115
27. Miyasaka, H., Murakami, M., Itaya, A., Guillaumont, D., Nakamura, S., and Irie, M. J. Am. Chem. Soc. 2001, 123, 753
28. Miyasaka, H., Murakami, M., Okada, T., Nagata, Y., Itaya, A., Kobatake, S., Nakamura, S., and Irie, M. Chem. Phys. Lett. 2003, 371, 40
29. Ishibashi, Y., Tani, K., Miyasaka, H., Kobatake, S., and Irie, M. Chem. Phys. Lett. 2007, 437, 243
30. Tani, K., Ishibashi, Y., Miyasaka, H., Kobatake, S., and Irie, M. J. Phys. Chem. C 2008, 112, 11150
31. Fukaminato, T., Doi, T., Tanaka, M., and Irie, M. J. Phys. Chem. C 2009, 113, 11623
32. Irie, M. and Sayo, K. J. Phys. Chem. 1992, 96, 7671
33. Uchida, K., Tsuchida, E, Aoi, Y., Nakamura, S., and Irie, M. Chem. Lett. 1999, 28, 63
34. Nakayama, T., Amijima, Y., Ibuki, K., and Hamanoue, K. Rev. Sci. Instrum. 1997, 68, 4364
35. Zi-lek, M., Lorenc, M., and Naskre-cki, R. Appl. Phys. B: Laser Opt. 2001, 72, 843
36. Aloïse, S., Réhault, J., Moine, B., Poizat, O., Buntinx, G., Lokshin, V., Valès, M., and Samat, A. J. Phys. Chem. A 2007, 111, 1737
37. Jacquemin, D., Perpète, E. A., Ciofini, I., and Adamo, C. Acc. Chem. Res. 2009, 42, 326
38. Maurel, F., Perrier, A., Perpète, E. A., and Jacquemin, D. J. Photochem. Photobiol. A 2008, 199, 211
39. Gaussian 03, Revision C.02. Frisch, M. J. et al. Gaussian, Inc., Wallingford, CT, 2004.
40. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
41. Adamo, C. and Barone, V. J. Chem. Phys. 1999, 110, 6158
42. Boese, A. D. and Martin, J. M. L. J. Chem. Phys. 2004, 121, 3405
43. Becke, A. D. J. Chem. Phys. 1993, 98, 1372
44. Tomasi, J., Mennucci, B., and Cammi, R. Chem. Rev. 2005, 105, 2999
45. Maurel, F., Aubard, J., Millie, P., Dognon, J. P., Rajzmann, M., Guglielmetti, R., and Samat, A. J. Phys. Chem. A 2006, 110, 4759
46. AMPAC 8, 1992-2004 Semichem, Inc., PO Box 1649, Shawnee, KS 66222.
47. Agmon, N., Rettig, W., and Groth, C. J. Am. Chem. Soc. 2002, 124, 1089
48. Gedeck, P. and Schneider, S. J. Photochem. Photobiol. A: Chem 1999, 121, 7
49. Lambert, C., Risko, C., Coropceanu, V., Schelter, J., Amthor, S., Gruhn, N., Durivage, J., and Bredas, J. L. J. Am. Chem. Soc. 2005, 127, 8508
50. Liotard, D. A. and Penot, J. P. Numerical Methods in the Study of Critical Phenomena; Springler-Verlag: Berlin, 1981; p 213.
51. Liotard, D. A. Int. J. Quantum Chem. 1992, 44, 723
52. Rauk, A. Orbital Interaction Theory of Organic Chemistry; John Wiley & Sons, Inc.: New York, 2001.
53. Perrier, A., Maurel, F., and Aubard, J. J. Photochem. Photobiol. A 2007, 189, 167