A theoretical study of the perfluoro-diarylethenes electronic spectra

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 199, Issue 2-3, 2008, Pages 211-223

  Maurel, François ^a   Perrier, Aurélie ^a   Perpète, Eric A ^b   Jacquemin, Denis ^b,c  

^a UNIVERSITÉ PARIS DIDEROT   (France)

^b UNIVERSITY OF NAMUR   (Belgium)

^c FUND FOR SCIENTIFIC RESEARCH   (Belgium)

Author keywords

Colour; Density functional theory; Diarylethenes; Electronic spectra; Photochromism

Indexed keywords

EID: 56349106872     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2008.05.018     Document Type: Article

References (155)

1. M. Irie, M. Mohri, J. Org. Chem. 53 (1988) 803.
2. Y. Nakayama, K. Hayashi, M. Irie, J. Org. Chem. 55 (1990) 2592.
3. S.L. Gilat, S.H. Kawai, J.M. Lehn, J. Chem. Soc., Chem. Commun. (1993) 1439.
4. M. Irie, K. Sakemura, M. Okinaka, K. Uchida, J. Org. Chem. 60 (1995) 8305.
5. S.L. Gilat, S.H. Kawai, J.M. Lehn, Chem. Eur. J. 1 (1995) 275.
6. M. Irie, Chem. Rev. 100 (2000) 1685.
7. B.L. Feringa, Molecular Switches, Wiley-VCH, Weinheim, 2001.
8. M.M. Krayushkin, Chem. Heterocycl. Compd. 37 (2001) 15.
9. H. Dürr, H. Bouas-Laurent, Photochromism Molecules and Systems, Elsevier, New York, 2003.
10. K. Matsuda, M. Irie, J. Photochem. Photobiol. C: Photochem. Rev. 5 (2004) 169.
11. H. Tian, S. Yang, Chem. Soc. Rev. 33 (2004) 85.
12. K. Uchida, S. Nakamura, M. Irie, Bull. Chem. Soc. Jpn. 65 (1992) 430.
13. M. Irie, K. Sayo, J. Phys. Chem. 96 (1992) 7671.
14. M. Hanazawa, R. Sumiya, Y. Horikawa, M. Irie, J. Chem. Soc., Chem. Commun. (1992) 206.
15. M.M. Krayushkin, V.A. Shirinyan, L.I. Belen'kii, A.A. Shimkin, A. Martynkin, B.M. Uzhinov, Russ. J. Org. Chem. 38 (2002) 1335.
16. M.M. Krayushkin, S.N. Ivanov, A.Y. Martynkin, B.V. Lichitsky, A.A. Dudinov, B.M. Uzhinov, Russ. Chem. Bull. 50 (2001) 116.
17. P.R. Hania, R. Telesca, L.N. Lucas, A. Pugzlys, J.H. van Esch, B.L. Feringa, J.G. Snijders, K. Duppen, J. Phys. Chem. A 106 (2002) 8498.
18. L.N. Lucas, J.J. de Jong, J.H. van Esch, R.M. Kellogg, B.L. Feringa, Eur. J.Org. Chem. (2003) 155.
19. Y. Chen, D.X. Zeng, M.G. Fan, Org. Lett. 5 (2003) 1435.
20. M.M. Krayushkin, D.V. Pashchenko, B.V. Lichitskii, T.M. Valova, Y.P. Strokach, V.A. Barachevskii, Russ. J. Org. Chem. 42 (2006) 1816.
21. Y. Chen, D.X. Zeng, N. Xie, Y.Z. Dang, J. Org. Chem. 70 (2005) 5001.
22. Y. Han, Z.B. Zhang, J.P. Xiao, W.P. Yan, M.G. Fan, Chin. Chem. Lett. 16 (2005) 175.
23. K. Matsuda, M. Irie, Chem. Eur. J. 7 (2001) 3466.
24. G. Guirado, C. Coudret, J.-P. Launay, J. Phys. Chem. C 111 (2007) 2770.
25. S. Kobatake, D. Takami, T. Muto, H. Ishikawa, M. Irie, Nature 446 (2007) 778.
26. S. Nakamura, M. Irie, J. Org. Chem. 53 (1988) 6136.
27. J. Ern, A.T. Benz, H.D. Martin, S. Mukamel, D. Schmid, S. Tretiaks, E. Tsiper, C. Kryschi, Chem. Phys. 246 (1999) 115.
28. J. Ern, A.T. Benz, H.D. Martin, S. Mukamel, S. Tretiaks, K. Tsyganenko, K. Kuldova, H.P. Trommsdorff, C. Kryschi, J. Phys. Chem. A 105 (2001) 1741.
29. D. Guillaumont, T. Kobayashi, K. Kanda, H. Miyasaka, K. Uchida, S. Kobatake, K. Shibata, S. Nakamura, M. Irie, J. Phys. Chem. A 106 (2002) 7222.
30. K. Uchida, D. Guillaumont, E. Tsuchida, G. Mochizuki, M. Irie, A. Murakami, S. Nakamura, J. Mol. Struct. (THEOCHEM) 579 (2002) 115.
31. Y. Asano, A. Murakami, T. Kobayashi, A. Goldberg, D. Guillaumont, S. Yabushita, M. Irie, S. Nakamura, J. Am. Chem. Soc. 126 (2004) 12112.
32. Y. Liu, Q. Wang, Y. Liu, X.Z. Yang, Chem. Phys. Lett. 373 (2003) 338.
33. Y. Asano, A. Murakami, T. Kobayashi, S. Kobatake, M. Irie, S. Yabushita, S. Nakamura, J. Mol. Struct. (THEOCHEM) 625 (2003) 227.
34. A. Goldberg, A. Murakami, K. Kanda, T. Kobayashi, S. Nakamura, K. Ucjida, H. Sekiya, T. Fukaminato, T. Kawau, S. Kobatake, M. Irie, J. Phys. Chem. A 107 (2003) 4982.
35. M. Cossi, V. Barone, J. Chem. Phys. 115 (2001) 4708.
36. G. Scalmani, M.J. Frisch, B. Mennucci, J. Tomasi, R. Cammi, V. Barone, J. Chem. Phys. 124 (2006) 094107.
37. M. Caricato, J. Mennucci, B. Tomasi, F. Ingrosso, R. Cammi, S. Corni, G. Scalmani, J. Chem. Phys. 124 (2006) 124520.
38. D. Jacquemin, J. Preat, E.A. Perpète, Chem. Phys. Lett. 410 (2005) 254.
39. D. Jacquemin, J. Preat, V. Wathelet, E.A. Perpète, J. Chem. Phys. 124 (2006) 074104.
40. D. Jacquemin, J. Preat, V. Wathelet, M. Fontaine, E.A. Perpète, J. Am. Chem. Soc. 128 (2006) 2072.
41. D.J. Tozer, J. Chem. Phys. 119 (2003) 12697.
42. S. Yokojima, K. Matsuda, M. Irie, A. Murakami, T. Kobayashi, S. Nakamura, J. Phys. Chem. A 110 (2006) 8137.
43. D. Jacquemin, E.A. Perpète, Chem. Phys. Lett. 429 (2006) 147.
44. D. Majumdar, H.M. Lee, J. Kim, K.S. Kim, B.J. Mhin, J. Chem. Phys. 111 (1999) 5866.
45. S. Kobatake, M. Morimoto, Y. Asano, A. Murakami, S. Nakamura, M. Irie, Chem. Lett. (2002) 1224.
46. M. Giraud, A. Léaustic, M.F. Charlot, P. Yu, M. Césario, C. Philouze, R. Pansu, K. Nakatani, E. Ishow, New. J. Chem. 29 (2005) 439.
47. K. Higashiguchi, K. Matsuda, A. Asano, A. Murakami, S. Nakamura, M. Irie, Eur. J. Org. Chem. (2005) 91.
48. A.E. Clark, J. Phys. Chem. A 110 (2006) 3790.
49. D.Z. Chen, Z. Wang, X. Zhao, J. Mol. Struct. (THEOCHEM) 774 (2006) 77.
50. G. Guirado, C. Coudret, M. Hliwa, J.-P. Launay, J. Phys. Chem. B 109 (2005) 17445.
51. A. Perrier, F. Maurel, J. Aubard, J. Photochem. Photobiol. A: Chem. 189 (2007) 167.
52. A. Perrier, F. Maurel, J. Aubard, J. Phys. Chem. A 111 (2007) 9688.
53. Y.C. Jeong, J.P. Han, Y. Kim, E. Kim, S.I. Yang, K.H. Ahn, Tetrahedron (2007) 3173.
54. E.A. Perpète, D. Jacquemin, J. Photochem. Photobiol. A: Chem. 187 (2007) 40.
55. A.M. Laurent, J.M. André , E.A. Perpète, D. Jacquemin, J. Photochem. Photobiol. A: Chem. 192 (2007) 211.
56. E.A. Perpète, F. Maurel, D. Jacquemin, J. Phys. Chem. A 111 (2007) 5528.
57. D. Jacquemin, E.A. Perpète, G.E. Scuseria, I. Ciofini, C. Adamo, J. Chem. Theory Comput. 4 (2008) 123.
58. T. Yanai, D.P. Tew, N.C. Handy, Chem. Phys. Lett. 393 (2004) 51.
59. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople Jr., Gaussian 03, Revision C.02 2004, Gaussian Inc., Wallingford, CT, 2004.
60. C. Adamo, V. Barone, J. Chem. Phys. 110 (1999) 6158.
61. M. Ernzerhof, G.E. Scuseria, J. Chem. Phys. 110 (1999) 5029.
62. J.P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 77 (1996) 3865.
63. J.-F. Guillemoles, V. Barone, L. Joubert, C. Adamo, J. Phys. Chem. A 106 (2002) 11354.
64. L. Petit, C. Adamo, N. Russo, J. Phys. Chem. B 109 (2005) 12214.
65. A.D. Quartarolo, N. Russo, E. Sicilia, Chem. Eur. J. 12 (2006) 6797.
66. D. Jacquemin, M. Bouhy, E.A. Perpète, J. Chem. Phys. 124 (2006) 204321.
67. A. Pezzella, L. Panzella, O. Crescenzi, A. Napolitano, S. Navaratman, R. Edge, E. Land, V. Barone, M. d'Ischia, J. Am. Chem. Soc. 128 (2006) 15490.
68. J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 105 (2005) 2999.
69. C.A. Bertolino, A.M. Ferrari, C. Barolo, G. Viscardi, G. Caputo, S. Coluccia, Chem. Phys. 330 (2006) 52.
70. Heptane, forwhich the standard parameters have been defined inGaussian03, has been used instead of hexane for these calculations.
71. Heptane, forwhich the standard parameters have been defined inGaussian03, has been used instead of 3-methyl-pentane for these calculations.
72. For diethyl-ether, we have used: EPSINF = 1.828.
73. Ethyl acetate, as diethylether except for: EPS = 6.02, EPSINF = 1.89 which have been set following available physico-chemical data.
74. Note that vibrational, analysis has been performed for each molecule in a single solvent, but not in all solvents in order to gain cpu-time.
75. C. Adamo, G.E. Scuseria, V. Barone, J. Chem. Phys. 111 (1999) 2889.
76. L.A. Curtiss, K. Raghavachari, P.C. Referm, J.A. Pople, Chem. Phys. Lett. 270 (1997) 419.
77. V. Barone, C. Adamo, J. Chem. Phys. 105 (1996) 11007.
78. A. Peters, R. McDonald, N.R. Branda, Chem. Commun. (2002) 2274.
79. I. Ciofini, C. Adamo, J. Phys. Chem. A 111 (2007) 5549.
80. K. Burke, J. Werschnik, E.K.U. Gross, J. Chem. Phys. 123 (2005) 062206.
81. D. Guillaumont, S. Nakamura, Dyes Pigments 46 (2000) 85.
82. J. Fabian, Theor. Chem. Acc. 106 (2001) 199.
83. J. Fabian, L.A. Diaz, G. Seifert, T. Niehaus, J. Mol. Struct. (THEOCHEM) 594 (2002) 41.
84. J.L. Brédas, Adv. Mater. 7 (1995) 263.
85. C.H. Choi, M. Kertesz, A. Karpfen, J. Chem. Phys. 107 (1997) 6712.
86. R. Pino, G. Scuseria, J. Chem. Phys. 121 (2004) 8113.
87. D. Jacquemin, E.A. Perpète, I. Ciofini, C. Adamo, Chem. Phys. Lett. 405 (2005) 376.
88. D. Jacquemin, A. Femenias, H. Chermette, I. Ciofini, C. Adamo, J.M. André, E.A. Perpète, J. Phys. Chem. A 110 (2006) 5952.
89. M. Irie, T. Lifka, S. Kobatake, N. Kato, J. Am. Chem. Soc. 122 (2000) 4871.
90. S. Kobatake, M. Yamada, T. Yamada, M. Irie, J. Am. Chem. Soc. 121 (1999) 8450.
91. T. Yamada, S. Kobatake, K. Muto, M. Irie, J. Am. Chem. Soc. 122 (2000) 1589.
92. S. Kobatake, K. Shibata, K. Uchida, M. Irie, J. Am. Chem. Soc. 122 (2000) 12135.
93. M. Irie, S. Kobatake, M. Horichi, Science 291 (2001) 1769.
94. M. Takeshita, M. Ogawa, K. Miyata, T. Tamato, J. Phys. Org. Chem. 16 (2003) 148.
95. M. Irie, K. Uchida, T. Eriguchi, H. Tsuzuki, Chem. Lett. (1995) 899.
96. K. Uchida, M. Irie, Chem. Lett. (1995) 969.
97. M. Irie, T. Eriguchi, T. Takada, K. Uchida, Tetrahedron 53 (1997) 1263.
98. S. Kobatake, M. Irie, Tetrahedron 59 (2003) 8359.
99. K. Uchida, T. Matsuoka, K. Sayo, M. Iwamoto, S. Hayashi, M. Irie, Chem. Lett. (1999) 835.
100. A. Heynderickx, A.M. Kaou, C. Moustrou, A. Samat, R. Guglielmetti, New. J. Chem. 27 (2003) 1425.
101. H. Miyasaka, T. Nobuto, A. Itaya, N. Tamai, M. Irie, Chem. Phys. Lett. 269 (1997) 281.
102. L.N. Lucas, PhD Thesis, Rijksuniversiteit Groningen, Groningen, Netherlands, 2001.
103. W.R. Browne, J.J. deJong, T. Kudernac, M. Walko, L.N. Lucas, K. Uchida, J.H. van Esch, B.L. Feringa, Chem. Eur. J. 11 (2005) 6430.
104. Y.P. Strokach, T.M. Valova, Z.O. Golotyuk, V.A. Barachevsky, V.N. Yarovenko, M.A. Kalik, M.M. Krayushkin, Opt. Spectrosc. 99 (2005) 714.
105. M. Morimoto, M. Irie, Chem. Eur. J. 12 (2006) 4275.
106. V.A. Barachevsky, Y.P. Strokach, M.M. Krayushkin, Mol. Cryst. Liq. Cryst. 430 (2005) 181.
107. M.M. Krayushkin, M.A. Kalik, D.L. Dzhavadov, A.Y. Martynkin, A.V. Firsov, B.M. Uzhinov, Russ. Chem. Bull. 48 (1999) 971.
108. M.M. Krayushkin, M.A. Kalik, D.L. Dzhavadov, L.G. Vorontsova, Z.A. Starikova, A.Y. Martynkin, S.N. Ivanov, B.M. Uzhinov, Russ. Chem. Bull. 49 (2000) 1757.
109. S. Pu, F.S. Zhang, F. Sun, R.J. Wang, X.H. Zhou, S.K. Chan, Tetrahedron Lett. 44 (2004) 1011.
110. M. DelZoppo, A. Lucotti, G. Zerbi, Vib. Spectrosc. 43 (2007) 249.
111. N. Tamai, T. Saika, T. Shimidzu, M. Irie, J. Phys. Chem. 100 (1996) 4689.
112. K. Uchida, N. Izumi, S. Sukata, Y. Kojima, S. Nakamura, M. Irie, Angew. Chem. Int. Ed. Engl. 45 (2006) 6470.
113. S. Pu, J. Xu, L. Shen, Q. Xiao, T. Yang, G. Li, Tetrahedron Lett. 46 (2005) 871.
114. S. Pu, T. Yang, Y. Wang, F. Zhang, J. Xu, Spectrochim. Acta A 66 (2007) 335.
115. A. Peters, N.R. Branda, Chem. Commun. (2003) 954.
116. M. Morimoto, S. Kobatake, M. Irie, Mol. Cryst. Liq. Cryst. 431 (2005) 151.
117. M. Murakami, H. Miyasaka, T. Okada, S. Kobatake, M. Irie, J. Am. Chem. Soc. 126 (2004) 14764.
118. P.R. Hania, A. Pugzlys, L.N. Lucas, J.J.D. deJong, B.L. Feringa, J.H. van Esch, H.T. Jonkman, K. Duppen, J. Phys. Chem. A 109 (2005) 9437.
119. W.R. Browne, J.J. deJong, T. Kudernac, M. Walko, L.N. Lucas, K. Uchida, J.H. van Esch, B.L. Feringa, Chem. Eur. J. 11 (2005) 6414.
120. S. Kobatake, K. Uchida, E. Tsuchida, M. Irie, Chem. Lett. (2000) 1340.
121. K. Morimitsu, K. Shibata, S. Kobatake, M. Irie, J. Org. Chem. 67 (2002) 4574.
122. S. Yamamoto, K. Matsuda, M. Irie, Chem. Eur. J. 9 (2003) 4878.
123. S. Yamamoto, K. Matsuda, M. Irie, Angew. Chem. Int. Ed. 42 (2003) 1636.
124. S. Pu, T. Yang, G. Li, J. Xu, B. Chen, Tetrahedron Lett. 47 (2006) 3167.
125. S. Pu, T. Yang, B. Yao, Y. Wang, M. Lei, J. Xu, Mater. Lett. 61 (2007) 855.
126. S. Pu, Q. Xiao, J.K. Xu, L. Shen, G.Z. Li, B. Chen, Chin. J. Chem. 24 (2006) 463.
127. S. Pu, T. Yang, J. Xu, L. Shen, G. Li, Q. Xiao, B. Chen, Tetrahedron 61 (2005) 6623.
128. S.H. Kawai, S.L. Gilat, J.M. Lehn, J. Chem. Soc., Chem. Commun. (1994) 1011.
129. S.H. Kawai, S.L. Gilat, R. Ponsinet, J.M. Lehn, Chem. Eur. J. 1 (1995) 285.
130. J. Biteau, F. Chaput, K. Lahlil, J.P. Boilot, G.M. Tsivgoulis, J.M. Lehn, B. Darracq, C. Marois, Y. Lévy, Chem. Mater. 10 (1945) 19998.
131. M. Morimoto, S. Kobatake, M. Irie, Chem. Eur. J. 9 (2003) 621.
132. X.D. Liu, Z.H. Chen, G.F. Fan, F.S. Zhang, Chin. J. Chem. 24 (2006) 1462.
133. S. Iwata, Y. Ishihara, C.P. Qian, I. Tanaka, J. Org. Chem. 57 (1992) 3726.
134. K. Uchida, T. Ishikawa, M. Takeshita, M. Irie, Tetrahedron 54 (1998) 6627.
135. K. Higashiguchi, K. Matsuda, M. Matsuo, T. Yamada, M. Irie, J. Photochem. Photobiol. A. 152 (2002) 141.
136. T. Fukaminato, T. Kawai, S. Kobatake, M. Irie, J. Phys. Chem. B 107 (2003) 8372.
137. S. Takami, T. Kawai, M. Irie, Eur. J. Org. chem. (2002) 3796.
138. F. Sun, F. Zhang, H. Guo, X. Zhou, R.Wang, F. Zhao, Tetrahedron 59 (2003) 7615.
139. S. Takami, M. Irie, Tetrahedron 60 (2004) 6155.
140. S. Pu, T. Yang, J. Xu, B. Chen, Tetrahedron Lett. 47 (2006) 6473.
141. T. Yamaguchi, Y. Fujita, M. Irie, Chem. Commun. (2004) 1010.
142. M. Irie, K. Uchida, Bull. Chem. Soc. Jpn. 71 (1998) 985.
143. T. Yamaguchi, M. Irie, Tetrahedron Lett. 47 (2006) 1267.
144. K. Uchida, S. Nakamura, M. Irie, Res. Chem. Intermediat. 21 (1995) 861.
145. K. Yagi, M. Irie, Bull. Chem. Soc. Jpn. 76 (2003) 1625.
146. T. Yamaguchi, M. Irie, Bull. Chem. Soc. Jpn. 79 (2006) 1100.
147. K. Uchida, E. Tsuchida, Y. Aoi, S. Nakamura, M. Irie, Chem. Lett. (1999) 63.
148. M. Frigoli, G.H. Mehl, Chem. Commun. (2004) 818.
149. E. Kim, M. Kim, K. Kim, Tetrahedron 62 (2006) 6814.
150. K. Matsuda, M. Irie, Tetrahedron Lett. 41 (2000) 2577.
151. T. Yamaguchi, Y. Fujita, H. Nakazumi, S. Kobatake, M. Irie, Tetrahedron 60 (2004) 9863.
152. N. Taifuji, K. Matsuda, M. Irie, Org. Lett. 7 (2005) 3777.
153. T. Yamaguchi, M. Irie, J. Photochem. Photobiol. A 178 (2006) 162.
154. Y.C. Jeong, D.G. Park, E. Kim, K.H. Ahn, S.I. Yang, Chem. Commun. (2006) 1881.
155. Y.C. Jeong, S.I. Yang, K.H. Ahn, E. Kim, Chem. Commun. (2005) 2503.