Photoswitchable Molecular Systems Based on Spiropyrans and Spirooxazines

Molecular Switches, Second Edition

Volumn 1, Issue , 2011, Pages 37-80

  Minkin, Vladimir I ^a  

^a SOUTHERN FEDERAL UNIVERSITY   (Russian Federation)

Author keywords

Biological activities; Biphotochromic systems; Bistability; Fluorescence; FRET (fluorescent resonance energy transfer); Merocyanines; Nanoparticles; Photochromic reactions; Photodynamic sensors; Photoresponsive polymers; Physical properties; Spirooxazines; Spiropyrans

Indexed keywords

EID: 84875732708     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527634408.ch2     Document Type: Chapter

References (246)

1. Aviram, A. (1998) J. Am. Chem. Soc., 110, 5687.
2. Irie, M Ed Photochromism: Memories and Switches, Special issue of (2000) Chem. Rev., 100, 1683.
3. Feringa, BL. (2001) Molecular Switches, Wiley-VCH Verlag GmbH, Weinheim.
4. Pease, A.R., Jeppesen, J.O., Stoddart, J.F., Luo, Y., Collier, C.P. and Heath, J.R. (2001) Acc. Chem. Res., 34, 433.
5. Weibel, N, Grunder, S. and Mayor, M. (2007) Org. Biomol. Chem., 5, 2343.
6. Heath, JR. and Ratner, M.A. (2003) Phys. Today, 56, 43.
7. Green, JE., Choi, J.W., Boukai, A., Bunimovich, Y., Johnston-Halpern, E., Delonno, E., Luo, Y., Sheriff, B.A., Xu, K., Shin, Y.S., Tseng, H.-R., Stoddard, J.F. and Heath, J.R. (2007) Nature, 445, 414.
8. Minkin, VI. (2008) Russ. Chem. Bull. Int. Ed., 57, 687.
9. Willner, I. and Willner, B. (2000) Angew. Chem. Int. Ed., 29, 1180.
10. Willner, I and Katz, E. (2001) Trends Biotech., 19, 222.
11. Goeldner, M and Givens, R. (2005) Dynamic Studies in Biology, Wiley-VCH Verlag GmbH, Weinheim.
12. Organic Photochromism (IUPAC Technical Report). Prepared by Bouas-Laurent, H. and D̈urr, H. (2001) Pure Appl. Chem., 73, 639.
13. Brown, HG. (ed.)(1971) Photochromism, Techniques of Chemistry, vol. 3, John Wiley & Sons, Inc., New York.
14. Barachevsky, V.A., Lashkov, G.L. and Tsekhomsky, V.A. (1977) Photochromism and its Application, Khimiya, Moscow (in Russian).
15. Eltsov, A.V. (1990) Organic Photochromes, Consultants Bureau, New York.
16. D̈urr, H. and Bouas-Laurent, H (eds) (1990) Photochromism. Molecules and Systems, Elsevier, Amsterdam.
17. Crano, JC. and Guglielmetti, R. (eds) (1999) Organic Photochromic and Thermochromic Compounds, vols. 1, 2, Plenum Press, New York.
18. Fischer, E. and Hirshberg, Y. (1952) J. Chem. Soc., 4522.
19. Chaude, O. and Rumpf, P. (1953) C. R. Acad. Sci., 236, 697.
20. Heligman-Rim, R and Hirshberg, Y. (1962) J. Phys. Chem., 66, 2470.
21. Hirshberg, Y (1956) J. Am. Chem. Soc., 78, 2304.
22. Hirshberg, Y (1960) New Scientist, 7, 1243.
23. Lokshin, V., Samat, A. and Metelitsa, A.V. (2002) Russ. Chem. Rev. Int. Ed., 71, 893.
24. Lokshin, V, Samat, A., Metelitsa, A.V., Minkin, V.I. (2007) in Modern Approaches to the Synthesis of O- and N-Heterocycles, vol. 1, (eds T.S. Kaufman and E.L. Larghi), Research Signpost, Kerala, p. 187.
25. Guglielmetti, R. (1990) in Photochromism. Molecules and Systems (eds H. D̈urr and H. Bouas-Laurent), Elsevier, Amsterdam, p. 314.
26. Bertelson, R.C. (1999) in Organic Photochromic and Thermochromic Compounds, vol. 1, (eds J.C. Crano and R. Guglielmetti), Plenum Press, New York, p. 11.
27. Berkovic, G., Krongauz, V. and Weiss, V. (2000) Chem. Rev., 100, 1741.
28. Minkin, VI. (2004) Chem. Rev., 104, 2751.
29. Lukyanov, B.S. and Lukyanova, M.B. (2005) Chem. Het. Comp. Int. Ed., 41, 281.
30. Chu, N.Y.C. (1990) in Photochromism. Molecules and Systems (eds H. D̈urr and H. Bouas-Laurent), Elsevier, Amsterdam, pp. 493-509, 879-882.
31. Maeda, S. (1999) in Organic Photochromic and Thermochromic Compounds (eds J.C. Crano and R. Guglielmetti), vol. 1, Plenum Press, New York, pp. 85-110.
32. Feng, C.-G. and Wang, J.-Y. (2006) Chinese J. Org. Chem., 26, 1012.
33. Fan, M.-G., Yu, L. and Zhao, W. (1999) in Organic Photochromic and Thermochromic Compounds, vol. 1, (eds J.C. Crano and R. Guglielmetti), Plenum Press, New York, p. 141.
34. Irie, M. (2000) Chem. Rev., 100, 1685.
35. Kobatake, S and Irie, M. (2003) Ann. Rep. Prog. Chem. Sect. C., 99, 277.
36. Matsuda, K and Irie, M. (2004) J. Photochem. Photobiol. C., 5, 169.
37. Akimov, D.A., Fedotov, A.V., Koroteev, N.I., Levich, E.V., Magnitskii, S.A., Naumov, A.N., Sidorov-Biryukov, D.A., Sokolyuk, N.T. and Zheltikov, A.M. (1997) Opt. Mem. Neural Netw., 6, 31.
38. Belfield, KD., Liu, Y., Negres, R.A., Fan, M., Pan, G., Hagan, D.J. and Hernandez, F.E. (2002) Chem. Mater., 14, 3663.
39. Saita, S, Yamaguchi, T., Kawai, T. and Irie, M. (2005) Phys. Chem. Chem. Phys., 6, 2300.
40. Krysanov, S.A. and Alfimov, M.V. (1982) Chem. Phys. Lett., 91, 77.
41. Kalisky, Y, Orlowski, T.E. and Williams, D.J. (1983) J. Phys. Chem., 87, 5333.
42. Lenoble, C and Becker, R.S. (1986) J. Phys. Chem., 90, 62.
43. Ernsting, NP., Dick, B. and Arthen-Engeland, Th. (1990) Pure Appl. Chem., 62, 1483.
44. Ernsting, NP. and Arthen-Engeland, T. (1991) J. Phys. Chem., 95, 5502.
45. Aramaki, S and Atkinson, G.H. (1992) J. Am. Chem. Soc., 114, 438.
46. Zhang, JZ., Schwartz, B.J., King, J.C. and Harris, C.B. (1992) J. Am. Chem. Soc., 114, 10921.
47. Tamai, N and Masuhara, H. (1992) Chem. Phys. Lett., 191, 189.
48. Tamai, N and Masuhara, H. (2000) Chem. Rev., 100, 1875.
49. Chibisov, AK. and G̈orner, H. (1997) J. Photochem. Photobiol. A. Chem., 105, 261.
50. G̈orner, H (2001) Phys. Chem. Chem. Phys., 3, 416.
51. Antipin, SA., Petrukhin, A.N., Gostev, F.E., Marevtsev, V.S., Titov, A.A., Barachevsky, V.A., Strokach, Yu.P. and Sarkisov, O.M. (2000) Chem. Phys. Lett., 331, 378; (2002) Khim. Phys., 21, 10.
52. Asahi, T, Suzuki, M. and Masuhara, H. (2002) J. Phys. Chem. A, 106, 2335.
53. Hobley, J, Pfeifer-Fukumura, U., Bletz, M., Asahi, N., Masuhara, H. and Fukumura, H. (2002) J. Phys. Chem A, 106, 2265.
54. Rini, M, Holm, A.-K., Nibbering, E.T.J. and Fidder, H. (2003) J. Am. Chem. Soc., 125, 3028.
55. Holm, A-K., Mohammed, O.F., Rini, M., Mukhtar, E., Nibbering, E.T.J. and Fidder, H. (2005) J. Phys. Chem. A., 109, 8962.
56. Wohl, CJ. and Kuklauskas, D. (2005) J. Phys. Chem. B., 109, 22186.
57. Glebov, EM., Vorobyev, D. Yu., Grivin, V.P., Plyusnin, V.F., Metelitsa, A.V., Voloshin, N.A., Minkin, V.I. and Micheau, J.-C. (2006) Chem. Phys., 323, 490.
58. Poisson, L, Rafael, K.D., Soep, B., Mestdagh, J.-M. and Buntinx, G. (2007) J. Am. Chem. Soc., 128, 3169.
59. Celani, P., Bernardi, F., Olivucci, M. and Robb, M.A. (1997) J. Am. Chem. Soc., 119, 10815.
60. Horii, T, Abe, Y. and Nakao, R. (2001) J. Photochem. Photobiol. A., 144, 119.
61. Maurel, F, Aubard, J., Rajzmann, M., Guglielmetti, R. and Samat, A. (2002) J. Chem. Soc., Perkin Trans. 2., 1307.
62. Futami, Y, Chin, M.L.S., Kudoh, S., Takayanagi, M. and Nakata, M. (2003) Chem. Phys. Lett., 370, 460.
63. Sheng, Y, Leszcynski, J., Garcia, A.A., Rosario, R., Gust, D. and Springer, J. (2004) J. Phys. Chem. B., 108, 16233.
64. Maurel, F, Aubard, J., Millie, P., Dognon, J.P., Rajzmann, M., Guglielmetti, R. and Samat, A. (2006) J. Phys. Chem. A., 110, 4759.
65. Go'mez, I, Reguero, M. and Robb, M.A. (2006) J. Phys. Chem. A., 110, 3986.
66. Bahr, J.L., Kodis, G., Garza, L., Lin, S. and Moore, A.L. (2001) J. Am. Chem. Soc., 123, 7124.
67. Minkin, V.I., Metelitsa, A.V., Dorogan, I.V., Lukyanov, B.S., Besugliy, S.O. and Micheau, J.-C. (2005) J. Phys. Chem. A., 109, 9605.
68. Delbaere, S. and Vermeersch, G. (2008) J. Photochem. Photobiol. C., 9, 61.
69. Berthet, J, Delbaere, S., Carvalho, L.M., Vermeersch, G. and Coelho, P. (2006) Tetrahedron Lett., 47, 4903.
70. Yee, L.H., Hanley, T., Evans, R.A., Davis, T.P. and Ball, G.E. (2010) J. Org. Chem., 75, 2851.
71. Christie, R.M., Li, L.-J., Spark, R.A., Morgan, K.M., Boyd, A.S.F. and Lycka, A.J. (2005) J. Photochem. Photobiol. A, 169, 37.
72. Krongauz, V. (1979) Isr. J. Chem., 18, 3.
73. Li, Y, Zhou, J., Wang, Y., Zhang, F. and Song, X. (1998) J. Photochem. Photobiol. A. Chem., 113, 65.
74. Uznanski, P (2000) Synth. Met., 109, 281.
75. Hibino, Y., Moriyama, K., Suzuki, M. and Kishimoto, K. (1992) Thin Solid Films, 210/211, 562.
76. Gu, Z.-Z., Hayami, S., Meng, B.-O., Iyoda, T., Fujishima, A. and Sato, O. (2000) J. Am. Chem. Soc., 122, 10730.
77. Miyata, A., Matsushima, T., Ohki, H., Unuma, Y. and Higashigaki, Y. (1995) Adv. Mater. Opt. Electron., 5, 37.
78. Kobayashi, T (ed.) (1996) J-Aggregates, World Scientific, Singapore.
79. Yuzawa, T. and Takahashi, H. (1994) Mol. Cryst. Liq. Cryst., 246, 279.
80. G̈orner, H., Atabekyan, L.S. and Chibisov, A.K. (1996) Chem. Phys. Lett., 260, 59.
81. G̈orner, H (1998) Chem. Phys. Lett., 282, 381.
82. G̈orner, H and Chibisov, A.K. (2004) in Organic Photochemistry and Photobiology, 2nd edn, (eds W. Horspool, and F. Lenci), CRC Press, Boca Raton, p. 36-1.
83. Konorov, S.O., Sidorov-Biryukov, D.A., Bugar, I., Chorvat, C., Chorvat, D. and Zheltikov, A.M. Jr (2003) Chem. Phys. Lett., 381, 572.
84. Kellmann, A., Tfibel, F., Pottier, R., Guglielmetti, R., Samat, A. and Rajzmann, M. (1993) J. Photochem. Photobiol. A. Chem., 76, 77.
85. Ait, OA., Barachevsky, V.A., Alfimov, M.V. and Baskin, I.I. (1997) Mol. Cryst. Liq. Cryst., 297, 271.
86. Malkin, Ya.N., Krasieva, T.B. and Kuzmin, V.A. (1989) J. Photochem. Photobiol. A. Chem., 49, 75.
87. Zakharova, MI., Coudret, C., Pimienta, V., Micheau, J.C., Sliwa, M., Poizat, O., Buntinx, G., Delbaere, S., Vermeersch, G., Metelitsa, A.V., Voloshin, N., Minkin, V.I. (2011) Dyes and Pigments., 89, 324.
88. Metelitsa, A.V., Dorogan, I.V., Lukyanov, B.S., Minkin, V.I., Besugliy, S.O. and Micheau, J.-C. (2005) Mol. Cryst. Liq. Cryst., 430, 45.
89. Ortica, F. and Favaro, G. (2000) J. Phys. Chem., 104, 12179.
90. Metelitsa, AV., Micheau, J.-C., Voloshin, N.A., Voloshina, E.N. and Minkin, V.I. (2001) J. Phys. Chem. A., 105, 8417.
91. Metelitsa, AV., Lokshin, V., Micheau, J.-C., Samat, A., Guglielmetti, R. and Minkin, V.I. (2002) Phys. Chem. Chem. Phys., 4, 4340.
92. Berthet, J, Delbaere, S., Lokshin, V., Bochu, C., Samat, A., Guglielmetti, R. and Vermeersch, G. (2002) Photochem. Photobiol. Sci., 1, 333.
93. Voloshin, NA., Metelitsa, A.V., Micheau, J.-C., Voloshina, E.N., Besugliy, S.O., Shelepin, N.E., Minkin, V.I., Tkachev, V.V., Safoklov, B.B. and Aldoshin, S.M. (2003) Russ. Chem. Bull. Int. Ed., 52, 2038.
94. Kellmann, A., Tfibel, F. and Guglielmetti, R. (1995) J. Photochem. Photobiol. A., 91, 131.
95. Chibisov, AK. and G̈orner, H. (1999) J. Photochem. Photobiol. A., 103, 5211.
96. Chibisov, AK., Marevtsev, V.S. and G̈orner, H. (2003) J. Photochem. Photobiol. A., 159, 233.
97. Schneider, S. (1987) Z. Phys. Chem. Neue Folge., 154, 1222.
98. Aramaki, S and Atkinson, G.H. (1990) Chem. Phys. Lett., 170, 181.
99. Wilkinson, F, Worrall, D.R., Hobley, J., Jansen, L., Williams, S.L., Langley, A.J. and Matousek, P. (1996) J. Chem. Soc. Faraday Trans., 1331.
100. Buntinx, G, Foley, S., Lefumeux, C., Lokshin, V., Poizat, O. and Samat, A. (2004) Chem. Phys. Lett., 391, 33.
101. Hobley, J., Pfeifer-Fukumura, U., Bletz, M., Asahi, T., Masuhara, H. and Fukumura, H. (2002) J. Phys. Chem. A., 106, 2265.
102. Gaeva, EB., Pimenta, V., Metelitsa, A.V., Voloshin, N.A., Minkin, V.I. and Micheau, J.-C. (2004) J. Phys. Org. Chem., 18, 315.
103. Raymo, F.M. and Tomasulo, M. (2005) J. Phys. Chem. A., 109, 7343.
104. Seefeldt, B, Kasper, R., Beining, M., Mattay, J., Arden-Jacob, J., Kemnitzer, N., Drexhage, R.H., Heilemann, M. and Sauer, M. (2010) Photochem Photobiol. Sci., 9, 213.
105. Kuzmin, M.G. and Kozmenko, M.V. (1990) in Organic Photochromes, Chapter 6 (ed. A. Eltsov), Consultants Bureau, New York.
106. Minami, T., Tamai, N., Yamazaki, T. and Yamazaki, L. (1991) J. Phys. Chem., 95, 3988.
107. Winkler, JD., Bowen, C.M. and Michelet, V. (1998) J. Am. Chem. Soc., 120, 3237.
108. Kawata, S. and Kawata, Y. (2000) Chem. Rev., 100, 1777.
109. Manjikov, V.F., Darmanyan, A.P., Barachevsky, V.A. and Gerulaitis, Yu.N. (1972) Opt. Spectrosc. (Russ.), 32, 412.
110. Manjikov, V.F., Murin, V.A. and Barachevsky, V.A. (1973) Quantum Electron. (Russ.), 2, 66.
111. Parthenopoulos, D.A. and Rentzepis, P.M. (1989) Science, 24, 842.
112. Dvornikov, A.S., Cokgor, I., Wang, M., McCormick, F.B., Esener, S.C. and Rentzepis, P.M. Jr (1997) IEEE Trans. Comp. Pack. Manufact. Technol. A, 20, 203.
113. Liang, Y.C., Dvornikov, A.S. and Rentzepis, P.M. (2003) Proc. Natl. Acad. Sci., 100, 8109.
114. Dvornikov, AS., Liang, Y.C., Cruse, C.S. and Rentzepis, P.M. (2004) J. Phys. Chem. B., 108, 8652.
115. Minkin, V.I. (1994) Mol. Cryst. Liq. Cryst., 246, 9.
116. Voloshin, NA., Volbushko, N.V., Trofimova, N.S., Shelepin, N.E. and Minkin, V.I. (1994) Mol. Cryst. Liq. Cryst., 246, 41.
117. Guo, X., Zhang, D., Zhou, Y. and Zhu, D. (2003) J. Org. Chem., 68, 5681.
118. Wu, S., Luo, Y., Zeng, F., Chen, J., Chen, Y. and Tong, Z. (2007) Angew. Chem. Int. Ed., 46, 7015.
119. Meng, X., Zhu, W., Guo, Z., Wang, J. and Tian, H. (2006) Tetrahedron, 62, 9840.
120. Zhu, M.-Q., Zhu, L., Han, J.J., Wu, W., Hurst, J.K. and Li, A.D.Q. (2006) J. Am. Chem. Soc., 128, 4303.
121. Zhu, L, Wu, W., Zhu, M.-Q., Han, J.J., Hurst, J.K. and Li, A.D.Q. (2007) J. Am. Chem. Soc., 129, 3524.
122. Sheng, X, Peng, A., Fu, H., Liu, Y., Zhao, Y., Ma, Y. and Yao, J. (2007) Nanotechnology, 18, 145707.
123. Rlajin, R., Stoddart, F.J. and Grzybowski, B.A. (2010) Chem. Soc. Rev., 39, 2203.
124. G̈utlich, P., Garcia, Y. and Woike, Th. (2001) Coord. Chem. Rev., 219-221, 839.
125. Sato, O (2003) Acc. Chem. Res., 36, 692.
126. Einaga, Y (2006) J. Photochem. Photobiol. A., 7, 69.
127. Sato, O, Tao, J. and Zhang, Y.-Z. (2007) Angew. Chem. Int. Ed., 46, 2152.
128. Halcrow, MA. (2008) Chem. Soc. Rev, 37, 278.
129. Benard, S., Riviere, E., Yu, P., Nakatani, K. and Delois, J.F. (2001) Chem. Mater., 13, 159.
130. Aldoshin, S.M., Sanina, N.A., Minkin, V.I., Voloshin, N.A., Ikorskii, V.N., Ovcharenko, V.I., Smirnov, V.A. and Nagaeva, N.K. (2007) J. Mol. Struct., 826, 69.
131. Aldoshin, SM., Sanina, N.A., Nadtochenko, V.A., Yurieva, E.A., Minkin, V.I., Voloshin, N.A. and Ikorskii, V.N. (2007) Russ. Chem. Bull. Int. Ed., 56, 1095.
132. Sanina, NA., Aldoshin, S.M., Shilov, G.V., Kurganova, E.V., Yurieva, E.A., Voloshin, N.A., Minkin, V.I., Nadtochenko, V.A. and Morgunov, R.B. (2008) Russ. Chem. Bull. Int. Ed., 57, 1451.
133. Aldoshin, SM. (2008) Russ. Chem. Bull. Int. Ed., 57, 718.
134. Kashima, I., Okubo, M., Ono, Y., Ito, M., Kida, N., Hikita, M., Enomoto, M. and Kojima, N. (2005) Synth. Met., 153, 473.
135. Benard, S., Leaustic, A., Riviere, E., Yu, P. and Clement, R. (2001) Chem. Mater., 13, 3709.
136. Zhang, H., Yi, T., Li, F., Delahaye, F., Yu, P. and Clement, R. (2007) J. Photochem. Photobiol. A., 186, 173.
137. Lu, A.H., Salabas, E.L. and Scḧuth, F. (2007) Angew. Chem. Int. Ed., 46, 1222.
138. Einaga, Y. (2006) Bull. Chem. Soc. Japan., 79, 361.
139. Garnovskii, A.D., Ikorskii, V.N., Uraev, A.I., Vasilchenko, I.S., Burlov, A.S., Garnovskii, D.A., Lyssenko, K.A., Vlasenko, V.G., Shestakova, T.E., Koshchienko, Y.V., Kuz'menko, T.A., Divaeva, L.N., Bubnov, M.P., Rybalkin, V.P., Korshunov, O.Y., Pirog, I.V., Borodkin, G.S., Bren, V.A., Uflyand, I.E., Antipin, M.Y. and Minkin, V.I. (2007) J. Coord. Chem., 60, 1493.
140. Katsonis, N., Lubomska, M., Pollard, M.M., Feringa, B.L. and Rudolf, P. (2007) Prog. Surf. Sci., 82, 407.
141. Tsujioka, T and Irie, M. (2010) J. Photochem. Photobiol. C: Phototochem. Rev., 11, 1.
142. Del Canto, E, Flavin, K., Natali, M., Perova, T. and Giordani, S. (2010) Carbon, 48, 2815.
143. Dominguez, J.M., Rosas, R., Aburto, J., Terres, E., Lopez, A. and Martinez-Palou, R. (2009) Microporous Mesoporous Mater., 118, 121.
144. Benito-Lopez, F, Scarmagnani, S., Walsh, Z., Paull, B., Macka, M. and Diamond, D. (2009) Sens. Actuators B: Chem., 140, 295.
145. Sung, T., Feng, L., Gao, X. and Jiang, L. (2005) Acc. Chem. Res., 38, 644.
146. Wang, S, Song, Y. and Jiang, L. (2007) J. Photochem. Photobiol. C., 8, 18.
147. Bletz, M., Pfeifer-Fukumura, U., Kolb, U. and Baumann, W. (2002) J. Phys. Chem. A., 106, 2232.
148. Bunker, B., Kim, B., Houston, J., Rosario, R., Garcia, A., Hyes, M., Gust, D. and Picraux, S. (2003) Nano Lett., 3, 1723.
149. Rosario, R, Gust, D., Garcia, A.A., Hayes, M., Taraci, J.L., Dailey, J.W. and Picraux, S.T. (2004) J. Phys. Chem. B, 108, 12640.
150. Nayak, A, Liu, H. and Belfort, G. (2006) Angew. Chem. Int. Ed., 45, 4094.
151. Athanassiou, A, Klyva, M., Lakiotaki, K., Georgiou, S. and Fotakis, C. (2005) Adv. Mater., 17, 988.
152. Niazov, T., Shlyahovsky, B. and Willner, I. (2007) J. Am. Chem. Soc., 129, 6374.
153. Khairutdinov, R.F., Giertz, K., Hurst, J.K., Voloshina, T.N., Voloshin, N.A. and Minkin, V.I. (1998) J. Am. Chem. Soc., 120, 12707.
154. Khairutdinov, RF. and Hurst, J.K. (2001) Langmuir, 17, 6881.
155. Kopelman, R.A., Snyder, S.M. and Frank, N.L. (2003) J. Am. Chem. Soc., 125, 13684.
156. Zhang, C, Zhang, Z., Fan, M. and Yan, W. (2008) Dyes Pigments, 76, 832.
157. Zhang, Z., Zhang, C., Fan, M. and Yan, W. (2008) Dyes Pigments, 77, 469.
158. Kocer, A., Walko, M., Meijberg, W. and Feringa, B.L. (2005) Science, 309, 755.
159. Wen, G., Yan, J., Zhou, Y., Zhang, D., Mao, L. and Zhu, D. (2006) Chem. Commun., 3016.
160. Zhou, W., Chen, D., Li, J., Xu, J., Lv, J., Liu, H. and Li, Y. (2007) Org. Lett., 9, 3929.
161. Kim, S-H., Park, S.-Y., Shin, C.-J. and Yoon, N.-S. (2007) Dye Pigments., 72, 299.
162. Vlassiouk, I, Park, C.D., Vail, S.A., Gust, D. and Smirnov, S. (2006) Nano Lett., 6, 1013.
163. Zhu, L, Zhu, M.-Q., Hurst, J.K. and Li, A.D.Q. (2005) J. Am. Chem. Soc., 127, 8968.
164. Tomasulo, M, Yildiz, I. and Raymo, F.M. (2007) Inorg. Chim. Acta, 360, 938.
165. Medintz, IL., Trammell, S.A., Mattousi, H. and Mauro, J.M. (2004) J. Am. Chem. Soc., 126, 30.
166. Mayer, G. and Heckel, A. (2006) Angew. Chem. Int. Ed., 45, 4900.
167. Willner, I. (1997) Acc. Chem. Res., 30, 347.
168. Inoue, M (1999) in Organic Photochromic and Thermochromic Compounds, vol. 2, Chapter 9 (eds J.C. Crano and R. Guglielmetti), Plenum Press, New York, p. 391.
169. Willner, I and Willner, B (2001) in Molecular Switches Chapter 6 (ed. B.L. Feringa)Wiley-VCH Verlag GmbH, Weinheim, p 165.
170. Pieroni, O., Fissi, A., Angelini, N. and Lenci, F. (2001) Acc. Chem. Res., 34, 9.
171. Shao, N, Jin, J., Wang, H., Zheng, J., Yang, R., Chan, W. and Abliz, Z. (2010) J. Am. Chem. Soc., 132, 725.
172. Ciardelli, F., Fabbri, D., Pieroni, O. and Fissi, A. (1989) J. Am. Chem. Soc., 111, 3470.
173. Gartner, CA., Wen, B., Wan, J., Becker, R.S., Jones, G., Gygi, S.P. and Nelson, S.D. (2005) Biochem., 44, 1846.
174. Rijcken, C.J.F., Soga, O., Hennink, W.E. and van Nostrum, C.F. (2007) J. Control. Release, 120, 131.
175. Inoue, M., Kim, K. and Kitao, T. (1992) J. Am. Chem. Soc., 114, 778.
176. Shao, N., Jin, J.Y., Cheung, S.M., Yang, R.H., Chan, W.H. and Mo, T. (2006) Angew. Chem. Int. Ed., 45, 4944.
177. Shao, N., Gao, X., Wang, H., Yang, R. and Chan, W. (2009) Anal. Chim. Acta, 655, 1.
178. Phillips, J.P., Mueller, A. and Przystal, F. (1965) J. Am. Chem. Soc., 87, 420.
179. Taylor, LD., Nickolson, J. and Davis, R.B. (1967) Tetrahedron Lett., 8, 1585.
180. Atabekyan, LS., Roitman, G.P. and Chibisov, A.K. (1982) J. Anal. Chem. (Russ.)., 37, 293.
181. Winkler, J.D., Bowen, C.M. and Michelet, V. (1998) J. Am. Chem. Soc., 120, 778.
182. Collins, GE., Choi, L.S., Ewing, K.J., Bowen, C.M. and Winkler, J.D. (1999) Chem. Commun., 321.
183. Evans, L., Collins, G.E., Shaffer, R.E., Michelet, V. and Winkler, J.D. III (1999) Anal. Chem., 71, 5322.
184. Chernyshev, A.V., Metelitsa, A.V., Gaeva, E.B., Voloshin, N.A., Borodkin, G.S. and Minkin, V.I. (2007) J. Phys. Org. Chem., 20, 908.
185. Zacharova, MI., Pimienta, V., Metelitsa, A.V., Minkin, V.I. and Micheau, J.C. (2009) Russ. Chem. Bull. Int. Ed., 58, 1329.
186. Voloshin, N.A., Chernyshev, A.V., Raskita, I.M., Metelitsa, A.V. and Minkin, V.I. (2005) Russ. Chem. Bull. Int. Ed., 54, 705.
187. Chernyshev, AV., Voloshin, N.A., Raskita, I.M., Metelitsa, A.V. and Minkin, V.I. (2006) J. Photochem. Photobiol. A., 184, 289.
188. Zacharova, MI., Coudret, C., Pimienta, V., Micheau, J.C., Delbaere, S., Vermeersch, G., Metelitsa, A.V., Voloshin, N. and Minkin, V.I. (2010) Photochem. Photobiol. Sci, 9, 199.
189. Lu, N., Nguyen, V.N., Kumar, S. and McCurdy, A. (2005) J. Org. Chem., 70, 9067.
190. Minkovska, S., Kolev, K., Jeliazkova, B. and Deligeorgiev, T. (1998) Dyes Pigm., 39, 25.
191. Minkovska, S, Fedieva, M., Jeliazkova, B. and Deligeorgiev, T. (2004) Polyhedron, 23, 3147.
192. Jeliazkova, B., Minkovska, S. and Deligeorgiev, T. (2005) J. Photochem. Photobiol. A., 171, 153.
193. Alhashimy, N, Byrne, R., Minkovska, S. and Diamond, D. (2009) Tetrahedron Lett., 50, 2573.
194. Valeur, A. and Leray, I. (2000) Coord. Chem. Rev., 205, 3.
195. Bren, VA. (2001) Russ. Chem. Rev. Int. Ed., 70, 1017.
196. Alfimov, MA., Fedorova, O.A. and Gromov, S.P. (2003) J. Photochem. Photobiol. A., 158, 183.
197. Kimura, K, Sakamoto, H. and Nakamura, M. (2003) Bull. Chem. Soc. Jpn., 76, 225.
198. Gokel, GW., Leevy, W.M. and Weber, M.E. (2004) Chem. Rev., 104, 2723.
199. Minkin, VI., Dubonosov, A.D. and Bren, V.A. (2008) Arkivoc, (4), 90.
200. Kimura, K., Yamashita, T., Kaneshige, M. and Yokoyama, M. (1992) Chem. Commun., 969.
201. Kimura, K., Mizutani, R., Yokoyama, M. and Arakawa, R. (1997) J. Am. Chem. Soc., 119, 2062.
202. Sakamoto, H, Takagaki, H., Nakamura, M. and Kimura, K. (2005) Anal. Chem., 77, 1999.
203. Roxburgh, C.J. and Sammes, P.G. (2006) Eur. J. Org. Chem., (4),.
204. Liu, Z., Jiang, L., Liang, Z. and Gao, Y. (2005) Tetrahedron Lett., 46, 885.
205. Liu, Z, Jiang, L., Liang, Z. and Gao, Y. (2005) J. Mol. Struct., 737, 267.
206. Fedorova, O.A., Gromov, S.P., Strokach, Yu.P., Pershina, Yu.V., Sergeev, S.A., Barachevsky, V.A., Pepe, G., Samat, A. and Guglielmetti, R. (1999) Russ. Chem. Bull., 48, 1950.
207. Fedorova, OA., Gromov, S.P., Strokach, Yu.P., Koshkin, A.V., Valoya, T.M., Alfimov, M.V., Feofanov, A.V., Alaverdian, I.S., Lokshin, V.A., Samat, A., Guglielmetti, R., Girling, R.B., Moore, J. and Hester, R.E. (2002) New J. Chem., 26, 1137.
208. Fedorova, OA., Gromov, S.P., Koshkin, A.V., Strokach, Yu.P., Barachevsky, V.A., Lokshin, V.A., Samat, A., Guglielmetti, R. and Alfimov, M.V. (2002) Russ. Chem. Bull., 51, 58.
209. Korolev, VV., Vorobyev, D. Yu., Glebov, E.M., Grivin, V.P., Plyusnin, V.F., Koshkin, A.V., Fedorova, O.A., Gromov, S.P., Alfimov, M.V., Shklyaev, Yu.V., Vshivkova, T.S., Rozhkova, Yu.S., Tolstikov, A.G., Lokshin, V.A. and Samat, A. (2007) J. Photochem. Photobiol. A., 192, 75.
210. Paramonov, S, Delbaere, S., Fedorova, O., Fedorov, Yu., Lokshin, V., Samat, A. and Vermeersch, G. (2010) J. Photochem. Photobiol. A: Chem., 209, 111.
211. Juris, A., Balzani, V., Barigelletti, F., Campagna, S. and Belser, P. (1988) Coord. Chem. Rev., 84, 85.
212. Meyer, TJ. (1989) Acc. Chem. Rev., 22, 163.
213. Otsuki, J, Akasaka, T. and Araki, K. (2008) Coord. Chem. Rev., 252, 32.
214. Kume, S and Nishihara, H. (2008) Dalton Trans., 3260.
215. Yam, V.W.-W., Ko, C.-C., Wu, L.-X., Wong, K.M.-C. and Cheung, K.-K. (2000) Organometallics, 19, 1820.
216. Bahr, J.L., Kodis, G., de la Garza, L., Lin, S., Moore, A.L., Moore, T.A. and Gust, D. (2001) J. Am. Chem. Soc., 123, 7124.
217. Querol, M., Bozic, B., Salluce, N. and Belser, P. (2003) Polyhedron, 22, 655.
218. Belser, P., de Cola, L., Hartl, F., Adamo, V., Bosic, B., Chriqui, Y., Iyer, V.M., Jukes, R.T.F., K̈uhni, J., Querol, M., Roma, S. and Salluce, N. (2006) Adv. Funct. Mater., 16, 195.
219. Ichimura, K. (1999) in Organic Photochromic and Thermochromic Compounds, vol. 2, Chapter 1 (eds J.C. Crano and R. Guglielmetti), Plenum Press, New York, pp. 9-62.
220. Moniruzzaman, M., Sabey, C.J. and Fernando, G.F. (2007) Polymer, 48, 255.
221. Sumaru, K., Ohi, K., Takagi, T., Kanamori, T. and Shinbo, T. (2006) Langmuir, 22, 4353.
222. Nishikori, H., Tanaka, N., Takagi, K. and Fujii, T. (2007) J. Photochem. Photobiol. A., 189, 46.
223. Kumar, A, Srivastava, A., Galaev, I. Yu. and Matiasson, B. (2007) Prog. Polymer Sci., 32, 1205.
224. McCoy, CP., Donnelly, L., Jones, D.S. and Gorman, S.O. (2007) Tetrahedron Lett., 48, 657.
225. Ubukata, T., Hara, M., Ichimura, K. and Seki, T. (2004) Adv. Mater., 16, 220.
226. Kim, S.-H., Park, S.-Y., Dhin, C.-J. and Yoon, N.-S. (2007) Dyes Pigments, 72, 299.
227. D̈urr, H. (1990) in Photochromism. Molecules and Systems (eds H. D̈urr and H. Bouas-Laurent), Elsevier, Amsterdam, p. 223.
228. Samat, A., Lokshin, V., Chamontin, K., Levy, D., Pepe, G. and Guglielmetti, R. (2001) Tetrahedron, 57, 7349.
229. Kinashi, K., Furuta, K., Harada, Y. and Ueda, Y. (2006) Chem. Lett., 35, 298.
230. de Silva, A.P., McGlenaghan, N.D. and McCoy, C.P. (2001) in Molecular Switches, Chapter 11 (ed. B.L. Feringa), Wiley, Wienheim, pp. 339-362.
231. de Silva, A.P. and McGlenaghan, N.D. (2004) Chem. Eur. J., 10, 574.
232. Callan, JF., de Silva, A.P. and Magri, D.C. (2005) Tetrahedron, 61, 8551.
233. Kang, T.J., Chang, S.H. and Kim, D.J. (1996) Mol. Cryst. Liq. Cryst., 278, 181.
234. Vlasenko, T. Ya., Marevtsev, V.S., Zaichenko, N.L. and Cherkashin, M.I. (1990) Izv. Akad. Nauk SSSR (Ser. Khim.)., 2179.
235. Luchina, V.G., Sychev, I. Yu., Marevtsev, V.S., Vlasenko, T. Ya., Khamchukov, Yu.D. and Cherkashin, M.I. (1992) Izv. Akad. Nauk SSSR (Ser. Khim.)., 2718.
236. D̈urr, H. (1999) in Organic Photochromic and Thermochromic Compounds, vol. 1 (eds J.C. Crano and R. Guglielmetti), Plenum Press, New York, pp. 231, 255.
237. Frigoli, M. and Mehl, G.H. (2005) Angew. Chem. Int. Ed., 44, 5048.
238. Delbaere, S, Vermeersch, G., Frigoli, M. and Mehl, G.H. (2006) Org. Lett., 8, 4931.
239. Mukhanov, E.L., Alexeenko, Yu.S., Lukyanov, B.S., Ryabuchin, Yu.I., Ryashchin, O.N. and Lukyanova, M.B. (2007) Khim. Get. Soed., (1), 129.
240. Mukhanov, E.L., Alexeenko, Yu.S., Dorogan, I.V., Tkachev, V.V., Lukyanov, B.S., Aldoshin, S.M., Besugliuy, S.O., Minkin, V.I., Utenyshev, A.N. and Ryaschzin, O.I. (2010) Khim. Get. Soed., 357.
241. Guo, X., Zhou, Y., Zhang, D., Yin, B., Liu, Z., Liu, C., Lu, Z., Huang, Y. and Zhu, D. (2004) J. Org. Chem., 69, 8924.
242. Liu, Z, Jiang, L., Liang, Z. and Gao, Y. (2005) J. Mol. Struct., 737, 267.
243. Cho, MJ., Kim, G.W., Jun, W.G., Lee, S.K., Jin, J.-I. and Choi, D.H. (2006) Thin Solid Films, 500, 52.
244. Gaeva, E.B., Pimienta, V., Delbaere, S., Metelitsa, A.V., Voloshin, N.A., Minkin, V.I., Vermeersch, G. and Micheau, J.C. (2007) J. Photochem. Photobiol. A: Chem., 191, 114.
245. Nakao, R., Horii, T., Kushino, Y., Shimaoka, K. and Abe, Y. (2002) Dyes Pigments., 52, 95.
246. Li, X., Li, J., Wang, Y., Matsuura, T. and Meng, J. (2004) J. Photochem. Photobiol. A., 161, 201.