Mechanistic insights in charge-transfer-induced luminescence of 1,2-dioxetanones with a substituent of low oxidation potential

Journal of the American Chemical Society

Volumn 127, Issue 24, 2005, Pages 8667-8679

  Isobe, Hiroshi ^a   Takano, Yu ^a   Okumura, Mitsutaka ^a   Kuramitsu, Seiki ^a   Yamaguchi, Kizashi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; DECOMPOSITION; LIGHT EMISSION; LUMINESCENCE; NEGATIVE IONS; OXIDATION; POLARIZATION; REDUCTION;

CHARGE-TRANSFER-INDUCED LUMINESCENCE (CTIL); MULTIREFERENCE MOLLER-PLESSET PERTURBATION (MRMP); PHENOXIDE ANIONS; SOLVENT EFFECTS;

CHARGE TRANSFER;

1,2 DIOXETANONE DERIVATIVE; PEROXIDE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; ELECTRON; ENERGY; LUMINESCENCE; OXIDATION; POLARIZATION; REACTION ANALYSIS; TEMPERATURE DEPENDENCE; THEORY; THERMAL ANALYSIS; VIBRATION;

EID: 20944447380     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja043295f     Document Type: Article

References (116)

1. (a) Beck, S.; Koster, H. Anal. Chem. 1990, 62, 2258.
2. (b) Mayer, A.; Neuenhofer, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 1044.
3. Adam, W.; Reinhardt, D.; Saha-Möller, C. R. Analyst 1996, 121, 1527.
4. Hastings, J. W. J. Mol. Evol. 1983, 19, 309.
5. McCapra, F. Q. Rev. Chem. Soc. 1966, 20, 485.
6. Wilson, T. Int. Rev. Sci., Phys. Chem. Ser. 2, 1976, 9, 265.
7. (a) Adam, W. Pure Appl. Chem. 1980, 52, 2591.
8. (b) Adam, W.; Cilento, G. In Chemical and Biological Generation of Excited States; Academic: New York, 1982.
9. Schuster, G. B. Acc. Chem. Res. 1979, 12, 366.
10. (a) Schmidt, S. P.; Schuster, G. B. J. Am. Chem. Soc. 1978, 100, 5559.
11. (b) Adam, W.; Baader, W. J. J. Am. Chem. Soc. 1985, 107, 410.
12. (a) Wilsey, S.; Bernardi, F.; Olivucci, M.; Robb, M. A.; Murphy, S.; Adam, W. J. Phys. Chem. A 1999, 103, 1669.
13. (b) Tanaka, C.; Tanaka, J. J. Phys. Chem. A 2000, 104, 2078.
14. (c) Rodríguez, E.; Reguero, M. J. Phys. Chem. A 2002, 106, 504.
15. (a) Yamaguchi, K. In Singlet Oxygen; Frimer, A. A., Ed.; CRC Press: Boca Raton, FL, 1985; Vol. III, p 119.
16. (b) Takano, Y.; Tsunesada, T.; Isobe, H.; Yoshioka, Y.; Yamaguchi, K.; Saito, I. Bull. Chem. Soc. Jpn. 1999, 72, 213.
17. (a) O'Neal, H. E.; Richardson, W. H. J. Am. Chem. Soc. 1970, 92, 6553.
18. (b) O'Neal, H. E.; Richardson, W. H. J. Am. Chem. Soc. 1971, 93, 1828.
19. (c) O'Neal, H. E.; Richardson, W. H. J. Am. Chem. Soc. 1972, 94, 8665.
20. (d) Richardson, W. H.; Montgomery, F. C.; Yelvington, M. B.; O'Neal, H. E. J. Am. Chem. Soc. 1974, 96, 7525.
21. (e) Richardson, W. H.; Lovett, M. B.; Olson, L. J. Org. Chem. 1989, 54, 3523.
22. (f) Wilson, T.; Golan, D. E.; Harris, M. S.; Baumstark, A. L. J. Am. Chem. Soc. 1976, 98, 1086.
23. (g) Koo, K. Y.; Schuster, G. B. J. Am. Chem. Soc. 1977, 99, 5403.
24. (a) Koo, J.-Y.; Schuster, G. B. J. Am. Chem. Soc. 1977, 99, 6107.
25. (b) Koo, J.-Y.; Schuster, G. B. J. Am. Chem. Soc. 1978, 100, 4496.
26. Koo, J.-Y.; Schmidt, S. P.; Schuster, G. B. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 30.
27. (a) Schmidt, S. P.; Schuster, G. B. J. Am. Chem. Soc. 1978, 100, 1966.
28. (b) Schmidt, S. P.; Schuster, G. B. J. Am. Chem. Soc. 1980, 102, 306.
29. (c) Schmidt, S. P.; Schuster, G. B. J. Am. Chem. Soc. 1980, 102, 7100.
30. (d) Dixon, B. G.; Schuster, G. B. J. Am. Chem. Soc. 1979, 101, 3116.
31. (a) Adam, W.; Simpson, G. A.; Yany, F. J. Phys. Chem. 1974, 78, 2559.
32. (b) Adam, W.; Cueto, O.; Yany, F. J. Am. Chem. Soc. 1978, 100, 2587.
33. (a) McCapra, F.; Beheshti, I.; Burford, A.; Hann, R. A.; Zaklika, K. A. J. Chem. Soc., Chem. Commun. 1977, 944.
34. (b) Zeklika, K. A.; Thayer, A. L.; Schaap, A. P. J. Am. Chem. Soc. 1978, 100, 4916.
35. Lee, C.; Singer, L. A. J. Am. Chem. Soc. 1980, 102, 3823.
36. (a) Adam, W.; Bronstein, I.; Trofimov, A. V.; Vasil'ev R. F. J. Am. Chem. Soc. 1999, 121, 958.
37. (b) Adam, W.; Trofimov, A. V. J. Org. Chem. 2000, 65, 6474.
38. (c) Adam, W.; Matsumoto, M.; Trofimov, A. V. J. Am. Chem. Soc. 2000, 122, 8631.
39. (a) Catalani, L. H.; Wilson, T. J. Am. Chem. Soc. 1989, 111, 2633.
40. (b) Wilson, T. Photochem. Photobiol. 1995, 62, 601.
41. White, E. H.; Roswell, D. F.; Dupont, A. C.; Wilson, A. A. J. Am. Chem. Soc. 1987, 109, 5189.
42. (a) McCapra, F. J. Photochem. Phoiobiol. A 1990, 51, 21.
43. (b) McCapra, F. Tetrahedron. Lett. 1993, 34, 6941.
44. (a) Bronstein, I.; Edwards, B.; Voyta, J. C. J. Biolumin. Chemilumin. 1988, 2, 186.
45. (b) Bronstein, I.; Edwards, B.; Voyta, J. C. J. Biolumin. Chemilumin. 1989, 4, 99.
46. (c) Edwards, B.; Sparks, A.; Voyta, J. C.; Bronstein, I. J. Biolumin. Chemilumin. 1990, 5, 1.
47. (d) Edwards, B.; Sparks, A.; Voyta, J. C.; Strong, R.; Murphy, O.; Bronstein, I. J. Org. Chem. 1990, 55, 6225.
48. (a) Schaap, A. P.; Handley, R. S.; Giri, B. P. Tetrahedron Lett. 1987, 28, 935.
49. (b) Schaap, A. P.; Chen, T. S.; Handley, R. S.; DeSylva, R.; Giri, B. P. Tetrahedron Lett. 1987, 28, 1155.
50. (c) Schaap, A. P.; Sandison, M. D.; Handley, R. S. Tetrahedron Lett. 1987, 28, 1159.
51. (a) Matsumoto, M.; Watanabe, N.; Kobayashi, H.; Azami, M.; Ikawa, H. Tetrahedron Lett. 1997, 38, 411.
52. (b) Matsumoto, M.; Watanabe, N.; Shiono, T.; Suganuma, H.; Matsubara, J. Tetrahedron Lett. 1997, 38, 5825.
53. Matsumoto, M.; Ishihara, T.; Watanabe, N.; Hiroshima, T. Tetrahedron Lett. 1999, 40, 4571.
54. Watanabe, N.; Suganuma, H.; Kobayashi, H.; Mutoh, H.; Katao, Y.; Matsumoto, M. Tetrahedron Lett. 1999, 55, 4287.
55. (e) Watanabe, N.; Kobayashi, H.; Azami, M.; Matsumoto, M. Tetrahedron Lett. 1999, 55, 6831.
56. (a) Goto, T.; Kishi, Y. Angew. Chem., Int. Ed. Engl. 1968, 7, 407.
57. (b) White, E. H.; Miano, J. D.; Umbreit, M. J. Am. Chem. Soc. 1975, 97, 198.
58. (c) McCapra, F. Acc. Chem. Res. 1976, 9, 201.
59. (a) Takabe, T.; Yamaguchi, K. Chem. Phys. Lett. 1976, 40, 347.
60. (b) Takabe, T.; Takenaka, K.; Yamaguchi, K.; Fueno, T. Chem. Phys. Lett. 1976, 44, 65. For the interrelationship between MO and CT theories, see Supporting Information.
61. (a) Yamaguchi, K. Chem. Phys. Lett. 1975, 33, 330.
62. (b) Yamaguchi, K. In Self-Consistent Field Theory and Applications; Carbo, R.; Klobukowski, M., Eds.; Elsevier: Amsterdam, 1990.
63. Yamaguchi, K.; Okumura, M.; Takada, K.; Yamanaka, S. Int. J. Quantum Chem., Quantum Chem. Symp. 1993, 27, 501.
64. (a) Isobe, H.; Takano, Y.; Kitagawa, Y.; Kawakami, T.; Yamanaka, S.; Yamaguchi, K.; Houk, K. N. Mol. Phys. 2002, 100, 717.
65. (b) Isobe, H.; Takano, Y.; Kitagawa, Y.; Kawakami, T.; Yamanaka, S.; Yamaguchi, K.; Houk, K. N. J. Phys. Chem. A 2003, 107, 682.
66. (c) Isobe, H.; Yamanaka, S.; Yamaguchi. K. Int. J. Quantum Chem. 2003, 95, 532.
67. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
68. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
69. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
70. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
71. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 4, 294.
72. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265.
73. (a) Gonzalez, C.; Schlegel, H. B. J. Chem. Phys 1989, 90, 2154.
74. (b) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523.
75. (a) Hirao, K. Chem. Phys. Lett. 1992, 190, 374.
76. (b) Hirao, K. Chem. Phys. Lett. 1992, 196, 397.
77. (c) Hirao, K. Int. J. Quantum Chem. 1992, S26, 517.
78. (d) Hirao, K. Chem. Phys. Lett. 1993, 201, 59.
79. (a) Siegbahn, P. E.; Heiberg, A.; Roos, B. O.; Levy, B. Phys. Scr. 1980. 21, 323.
80. (b) Roos, B. O.; Taylor, P. R.; Siegbahn, P. E. Chem. Phys. 1980, 48, 157.
81. (c) Roos, B. O. Int. J. Quantum Chem. 1980, S14, 175.
82. (a) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117.
83. (b) Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, 239.
84. (c) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, 327.
85. (d) Barone, V.; Cossi, M.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210.
86. (a) Wong, M. W.; Frisch, M. J.; Wiberg, K. B. J. Am. Chem. Soc. 1991, 113, 4776.
87. (b) Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Am. Chem. Soc. 1992, 114, 523.
88. (c) Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Chem. Phys. 1991, 95, 8991.
89. (d) Wong, M. W.; Wiberg, K. B.; Frisch, M. J. J. Am. Chem. Soc. 1992, 114, 1645.
90. Levine, I. N. In Quantum Chemistry Fifth Edition; Prentice Hall: 2000; p 593.
91. (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision E.3; Gaussian, Inc.: Pittsburgh, PA, 1995.
92. (b) 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.; 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.6; Gaussian, Inc.: Pittsburgh, PA, 1998.
93. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. J.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347.
94. The variations in the vertical electron affinity of the dioxetanone and dioxetane functionalities as a function of the O-O bond distance are summarized in Figure S6 (Supporting Information).
95. Schmidt, S. P.; Vincent, M. A.; Dykstra, C. E.; Schuster, G. B. J. Am. Chem. Soc. 1981, 103, 1292.
96. Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334.
97. (a) Deluca, M.; McElroy, W. D. Biochemistry 1974, 13, 921.
98. (b) McElroy, W. D.; Seliger, H. H.; White, E. H. Photochem. Photobiol. 1969, 10, 153.
99. (c) White, E. H.; Steinmetz, M. G.; Miano, J. D.; Wildes, P. D.; Moreland, R. J. Am. Chem. Soc. 1980, 102, 3199.
100. (d) White, E. H.; Roswell, D. F. Photochem. Photobiol. 1991, 53, 131.
101. Orlova, G.; Goddard, J. D.; Brovko, L. Y. J. Am. Chem. Soc. 2003, 125, 6962.
102. -1. In contrast, the addition of a phenoxide-anion group gives rise to the CT process, which corresponds to the nonstepwise mechanism; that is, no intermediate is formed.
103. (a) Landau, L. D. Phys. Zts. Sowiet. 1932, 2, 46.
104. (b) Zener, C. Proc. R. Soc. London, Ser. A 1933, 137, 696.
105. The results of the IRC analysis for para-1c are given in Figure S8 (Supporting Information).
106. (a) Stevani, C. V.; Silva, S. M.; Baader, W. J. Eur. J. Org. Chem. 2000, 4037.
107. (b) Silva, S. M.; Wagner, K.; Weiss, D.; Beckert, R.; Stevani, C. V.; Baader, W. J. Luminescence 2002, 17, 362.
108. Burshtein, A. I. Chem. Phys. 2003, 289, 251.
109. 2 moiety.
110. 1 states of para-1c and meta-1c calculated by the B3LYP method are shown in Figure S9 (Supporting Information).
111. 33d however, the HF method tends to overestimate the diradical character (yHOMO > 90%) for the back CT region, characterized by the B 3LYP method, and provides biased results in favor of diradical pathway (see Figure S2). Therefore, the calculations for the back CT region as well as the CT TSs were conducted using the B3LYP method.
112. -1.
113. We also tried to locate the equilibrium structures (min.) and the CT TSs of para- and meta-1c in benzene and DMSO at the PCM (for min.) or Onsager model (for CT TSs) B3LYP/6-31+G(d) levels. It was found that, despite the presence of the solvent reaction field, there are insignificant changes in the equilibrium geometries; however, the relatively large structural change of the CT TS on going from the gas phase to a solution is made explicit in the O-O distance and is largely dependent on the degree of solvent polarity. The detailed results are summarized in Table S3 (Supporting Information).
114. 15a
115. Kavarnos, G. J., Turro, N. J. Chem. Rev. 1986, 86, 401.
116. -1] of the methyl meta-oxybenzoate anion at the PCM HF/6-3I+G(d)//B3LYP/6-31+G(d) level.