Fluorescence modulation with photochromic switches

Journal of Physical Chemistry A

Volumn 109, Issue 33, 2005, Pages 7343-7352

  Raymo, Françisco M ^a   Tomasulo, Massimiliano ^a  

^a University of Miami   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COLORLESS STATE SWITCHES; ELECTRONIC MODIFICATION; FLUORESCENCE MODULATION; PHOTOCHROMIC COMPOUNDS;

ELECTRONIC STRUCTURE; FLUORESCENCE; IRRADIATION; LIGHT ABSORPTION; OPTICAL SWITCHES; QUENCHING; REDOX REACTIONS;

PHOTOCHROMISM;

EID: 24944518406     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp052440o     Document Type: Article

References (85)

1. Bouas-Laurent, H.; Dürr, H. Pure Appl. Chem. 2001, 73, 639-665.
2. Hirshberg, Y. Compt. Rend. Acad. Sci., Paris 1950, 231, 903-904.
3. Dorion, G. H.; Wiebe, A. F. Photochromism; Focal Press: New York, 1970.
4. Brown, G. H., Ed. Photochromism; Wiley: New York, 1971.
5. El'tsov, A. V., Ed. Organic Photochromes; Consultants Bureau: New York, 1990.
6. Bouas-Laurent, H., Dürr, H., Eds. Photochromism: Molecules and Systems; Elsevier: Amsterdam, 1990.
7. Crano, J. C., Guglielmetti R., Eds. Organic Photochromic and Thermochromic Compounds; Plenum Press: New York, 1999.
8. McArdle, C. B., Ed. Applied Photochromic Polymer Systems; Blackie: Glasgow, 1992.
9. Irie, M., Ed. Photo-Reactive Materials for Ultrahigh-Density Optical Memory; Elsevier: Amsterdam, 1994.
10. Irie, M. Chem. Rev. 2000, 100, 1683-1890.
11. The term photochromism derives from the Greek words "phos" and "chroma", which mean light and color respectively (ref 1).
12. The term photochromism is sometimes extended to processes that involve absorbance changes in the ultraviolet, rather than visible, region (ref 1).
13. Görner, H. Phys. Chem. Chem. Phys. 2001, 3, 416-423.
14. (a) Gegiu, D.; Muszkat, K. A.; Fischer, E. J. Am. Chem. Soc. 1968, 90, 3907-3918.
15. (b) Görner, H.; Gruen, H.; Schulte-Frohllnde, D. J. Phys. Chem. 1980, 84, 3031-3039.
16. Görner, H.; Fischer, C.; Gierisch, S.; Daub, J. J. Phys. Chem. 1993, 97, 4110-4117.
17. (a) Gross, H.; Dürr, H.; Retting, W. J. Photochem. 1984, 26, 165-178.
18. (b) Weber, C.; Rustemeyer, F.; Dürr, H. Adv. Mater. 1998, 10, 1348-1351.
19. Sheepwash, M.; Mitchell, R. H.; Bohne, C. J. Am. Chem. Soc. 2002, 124, 4693-4700.
20. Irie, M.; Sakemura, K.; Okinaza, M.; Uchida, K. J. Org. Chem. 1995, 60, 8305-8309.
21. Seibold, M.; Port, H.; Gustav, K. Chem. Phys. Lett. 1999, 314, 65-72.
22. Delaire, J. A.; Nakatani, K. In ref 10, pp 1817-1845.
23. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; 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, Rev. A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
24. Gauglitz, G. In ref 6, pp 15-63.
25. The kinetic model leading to the differential equations (1) and (2) assumes that the photoisomerization is performed in liquid solution at a fixed temperature under constant stirring, the pump and probe beams have identical path lengths, the quantum yields of photochemical processes other than the transformation of isomer A into B are all negligible.
26. -1.
27. The k values of thermally stable photochromes (e.g., 6 and 7) are negligible and their absorbance profiles are regulated solely by the first terms of the differential equations (1) and (2).
28. Kuz'min, M. G.; Koz'menko, M. V. In ref 5, pp 245-265.
29. Chibisov, A. K.; Görner, H. J. Phys. Chem. 1997, 101, 4305-4312.
30. (a) Liang, Y.; Dvornikov, A. S.; Rentzepis, P. M. Res. Chem. Intermed. 1998, 24, 905-914.
31. (b) Liang, Y.; Dvornikov, A. S.; Rentzepis, P. M. Chem. Commun. 2000, 1641-1642.
32. (c) Liang, Y.; Dvornikov, A. S.; Rentzepis, P. M. J. Mater. Chem. 2000, 10, 2477-2482.
33. (d) Liang, Y.; Dvornikov, A. S.; Rentzepis, P. M. J. Photochem. Photobiol. A. 2001, 146, 83-93.
34. (e) Liang, Y.; Dvornikov, A. S.; Rentzepis, P. M. Macromolecules 2002, 35, 9377-9382.
35. (f) Liang, Y.; Dvornikov, A. S.; Rentzepis, P. M. J. Mater. Chem. 2003, 13, 286-290.
36. (a) Spreitzer, H.; Daub, J. Liebigs Ann. 1995, 1637-1641.
37. (b) Daub, J.; Beck, M.; Knorr, A.; Spreitzer, H. Pure Appl. Chem. 1996, 68, 1399-1404.
38. (a) Fernández-Acebes, A.; Lehn, J.-M. Adv. Mater. 1998, 10, 1519-1522.
39. (b) Fernández-Acebes, A.; Lehn, J.-M. Chem. Eur. J. 1999, 5, 3285-3292.
40. Yagi, K.; Soong, C. F.; Irie, M. J. Org. Chem. 2001, 66, 5419-5423.
41. Ern, J.; Bens, A. T.; Martin, H.-D.; Mukamel, S.; Tretiak, S.; Tsyganenko, K.; Kuldova, K.; Trommsdorff, H. P.; Kryschi, C. J. Phys. Chem. A 2001, 105, 1741-1749.
42. Lim, S.-J.; An, B.-K.; Jung, S. D.; Chung, M. A.; Park, S. J. Angew. Chem., Int. Ed. 2004, 43, 6346-6350.
43. Kim, M.-S.; Kawai, T.; Irie, M. Opt. Mater. 2002, 21, 271-274.
44. Yam, V. W.-W.; Ko, C.-C; Zhu, N. J. Am. Chem. Soc. 2004, 126, 12734-12735.
45. (a) Tsivgoulis, G. M.; Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1119-1122.
46. (b) Tsivgoulis, G. M.; Lehn, J.-M. Chem. Eur. J. 1996, 2, 1399-1406.
47. Ern, J.; Bens, T.; Martin, H.-D.; Mukamel, S.; Tretiak, S.; Tsyganenko, K.; Kuldova, K.; Trommsdorf, H. P.; Kryschi, C. J. Phys. Chem. A 2001, 105, 1741-1749.
48. Frigoli, M.; Welch, C.; Mehl, G. J. Am. Chem. Soc. 2004, 126, 15382-15383.
49. (a) Liang, Y.; Dvornikov, A. S.; Rentzepis, P. M. Opt. Commun. 2003, 223, 61-66.
50. (b) Liang, Y.; Dvornikov, A. S.; Rentzepis, P. M. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 8109-8112.
51. (c) Liang, Y.; Dvornikov, A. S.; Rentzepis, P. M. J. Phys. Chem. B 2004, 108, 8652-8658.
52. (d) Dvornikov, A. S.; Liang, Y.; Rentzepis, P. M. J. Mater. Chem. 2005, 15, 1072-1078.
53. Ko, C.-C.; Wu, L.-X.; Wong, K. M.-C; Zhu, N.; Yam, V. W.-W. Chem. Eur. J. 2004, 10, 766-776.
54. Myles, A. J.; Branda, N. R. J. Am. Chem. Soc. 2001, 123, 177-178.
55. (a) Andréasson, J.; Kodis, G.; Terazono, Y.; Liddell, P. A.; Bandyopadhyay, S.; Mitchell, R. H.; Moore, T. A.; Moore, A. L.; Gust, D. J. Am. Chem. Soc. 2004, 126, 15926-15927.
56. (b) Terazono, Y.; Kodis, G.; Andréasson, J.; Jeong, G.; Brune, A.; Hartmann, T.; Dürr, H.; Moore, T. A.; Moore, A. L.; Gust, D. J. Phys. Chem. B 2004, 108, 1812-1814.
57. Saika, T.; Iyoda, T.; Honda, K.; Shimidzu, T. J. Chem. Soc., Chem. Commun. 1992, 591-592.
58. Tsuchiya, S. J. Am. Chem. Soc. 1999, 121, 48-53.
59. Reddy, D. R.; Maiya, B. G. Chem. Commun. 2001, 117-118.
60. Otsuki, J.; Suka, A.; Yamazaki, K.; Abe, H.; Araki, Y.; Ito, O. Chem. Commun. 2004, 1290-1291.
61. Archut, A.; Azzellini, G. C.; Balzani, V.; De Cola, L.; Vögtle, F. J. Am. Chem. Soc. 1998, 120, 12187-12191.
62. Inada, T.; Uchida, S.; Yokoyama, Y. Chem. Lett. 1997, 321-322.
63. Bahr, J. L.; Kodis, G.; de la Garza, L.; Lin, S.; Moore, A. L.; Moore, T. A.; Gust, D. J. Am. Chem. Soc. 2001, 123, 7124-7133.
64. (a) Giordano, L.; Jovin, T. M.; Irie, M.; Jares-Erijman, E. A. J. Am. Chem. Soc. 2002, 124, 7481-7489.
65. (b) Irie, M.; Fukaminato, T.; Sasaki, T.; Tamai, N.; Kawai, T. Nature 2002, 420, 759-760.
66. (c) Kim, M.-S.; Kawai, T.; Irie, M. Opt. Mater. 2002, 275-278.
67. (d) Fukaminato, T.; Sasaki, T.; Kawai, T.; Tamai, N.; Irie, M. J. Am. Chem. Soc. 2004, 126, 14843-14849.
68. Jin, M.; Lu, R.; Bao, C. Y.; Xu, T. H.; Zhao, Y. Y. Opt. Mater. 2004, 26, 85-88.
69. Harbron, E. J.; Vicente, D. A.; Hoyt, M. T. J. Phys. Chem. B 2004, 108, 18789-18792.
70. Kozlov, D. V.; Castellano, F. N. J. Phys. Chem. A 2004, 108, 10619-10622.
71. (a) Norsten, T. B.; Branda, N. R. Adv. Mater. 2001, 13, 347-349.
72. (b) Norsten, T. B.; Branda, N. R. J. Am. Chem. Soc. 2001, 123, 1784-1785.
73. (c) Myles, A. J.; Branda, N. R. Adv. Funct. Mater. 2002, 12, 167-173.
74. Osuka, A.; Fujikane, D.; Shinmori, H.; Kobatake, S.; Irie, M. J. Org. Chem. 2001, 66, 3913-3923.
75. Jukes, R. T.; Adamo, V.; Hartl, F.; Belser, P.; De Cola, L. Inorg. Chem. 2004, 43, 2779-2792.
76. Kawai, T.; Sasaki, T.; Irie, M. Chem. Commun. 2001, 711-712.
77. Guo, X.; Zhang, D.; Zhou, Y.; Zhu, D. J. Org. Chem. 2003, 68, 5681-5687.
78. (a) Walz, J.; Ulrich, K.; Port, H.; Wolf, H. C.; Wonner, J.; Effenberg, F. Chem. Phys. Lett. 1993, 213, 321-324.
79. (b) Seibold, M.; Port, H.; Wolf, H. C. Mol. Cryst. Liq. Cryst. 1996, 283, 75-80.
80. (c) Port, H.; Hennrich, M.; Seibold, M.; Wolf, H. C. Proc. Electrochem. Soc. 1998, 98, 61-70.
81. (d) Port, H.; Hartschuh, A.; Hennrich, M.; Wolf, H. C.; Endtner, J. M.; Effenberger, F. Mol. Cryst. Liq. Cryst. 2000, 344, 145-150.
82. (e) Ramsteiner, I. B.; Hartschuh, A.; Port, H. Chem. Phys. Lett. 2001, 343, 83-90.
83. Raymo, F. M.; Giordani, S. Org. Lett. 2001, 3, 1833-1836.
84. (a) Raymo, F. M.; Giordani, S. J. Am. Chem. Soc. 2002, 124, 2004-2007.
85. (b) Tomasulo, M.; Giordani, S.; Raymo, F. M. Adv. Fund. Mater. 2005, 15, 787-794.