Singlet sigma: The "other" singlet oxygen in solution

Photochemistry and Photobiology

Volumn 70, Issue 4, 1999, Pages 369-379

  Weldon, Dean ^a   Poulsen, Tina D ^a   Mikkelsen, Kurt V ^b   Ogilby, Peter R ^a  

^a AARHUS UNIVERSITY   (Denmark)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001039093     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(1999)070<0369:sstsoi>2.3.co;2     Document Type: Review

References (102)

1. Foote, C. S., J. S. Valentine, A. Greenberg and J. F. Liebman (1995) Active Oxygen in Chemistry. Chapman and Hall, London.
2. Wayne, R. P. (1985) Reactions of singlet molecular oxygen in the gas phase. In Singlet Oxygen, Vol. 1 (Edited by A. A. Frimer), pp. 81-175. CRC Press, Boca Raton, FL.
3. Krasnovsky, A. A. (1979) Photoluminescence of singlet oxygen in pigment solutions. Photochem. Photobiol. 29, 29-36.
4. Khan, A. U. and M. Kasha (1979) Direct spectroscopic observation of singlet oxygen emission at 1268 nm excited by sensitizing dyes of biological interest in liquid solution. Proc. Natl. Acad. Sci. USA 76, 6047-6049.
5. Salokhiddinov, K. I., I. M. Byteva and B. M. Dzhagarov (1979) Duration of the luminescence of singlet oxygen in solution following pulsed laser excitation. Opt. Spektrosk. 47, 881-886.
6. Hurst, J. R., J. D. McDonald and G. B. Schuster (1982) Lifetime of singlet oxygen in solution directly determined by laser spectroscopy. J. Am. Chem. Soc. 104, 2065-2067.
7. Parker, J. G. and W. D. Stanbro (1982) Optical determination of the collisional lifetime of singlet molecular oxygen in acetone and deuterated acetone. J. Am. Chem. Soc. 104, 2067-2069.
8. Ogilby, P. R. and C. S. Foote (1982) Singlet molecular oxygen luminescence in solution following pulsed laser excitation. Solvent deuterium isotope effects on the lifetime of singlet oxygen. J. Am. Chem. Soc. 104, 2069-2070.
9. 1Δg) in liquid water as determined by time-resolved infrared luminescence measurements. J. Am. Chem. Soc. 104, 5541-5543.
10. - chemiluminescence upon decomposition of 1,4-dimethylnaphthalene endoperoxide. Chem. Phys. Lett. 122, 87-92.
11. + oxygen in solution. J. Phys. Chem. 97, 193-195.
12. 2. J. Phys. Chem. 99, 15919-15924.
13. 1Δg) emission spectrum. J. Phys. Chem. A 102, 1498-1500.
14. g fluorescence of molecular oxygen in solutions. J. Appl. Spectrosc. (Zhur. Prik. Spek.) 65, 1-4.
15. Keszthelyi, T., D. Weldon, T. N. Andersen, T. D. Poulsen, K. V. Mikkelsen and P. R. Ogilby (1999) Radiative transitions of singlet oxygen: new tools, new techniques, and new interpretations. Photochem. Photobiol. 70, 4, 531-539.
16. +) in solution. Phosphorescence from an upper excited state. J. Phys. Chem. 98, 2874-2876.
17. 2) vibronic emission in solution. J. Am. Chem. Soc. 118, 3031-3032.
18. g) formation in the primary steps of triplet state photosensitization in solution. Chem. Phys. Lett. 213, 111-116.
19. Weldon, D. and P. R. Ogilby (1998) Time-resolved absorption spectrum of singlet oxygen in solution. J. Am. Chem. Soc. 120, 12978-12979.
20. Ogilby, P. R. (1999) Solvent effects on the radiative transitions of singlet oxygen. Acc. Chem. Res. 32, 512-519.
21. 1Δg). J. Phys. Chem. 91, 4599-4602.
22. 1Δg). J. Phys. Chem. 99, 3521-3526.
23. 1Δg). J. Phys. Chem. 94, 4377-4378.
24. 1Δg singlet oxygen. J. Phys. Chem. 102, 9833-9837.
25. Gorman, A. A., A. A. Krasnovsky and M. A. J. Rodgers (1991) Singlet oxygen infrared luminescence: unambiguous confirmation of a solvent-dependent radiative rate constant. J. Phys. Chem. 95, 598-601.
26. Bromberg, A. and C. S. Foote (1989) Solvent shift of singlet oxygen emission wavelength. J. Phys. Chem. 93, 3968-3969.
27. Macpherson, A. N., T. G. Truscott and P. H. Turner (1994) Fourier-transform luminescence spectroscopy of solvated singlet oxygen. J. Chem. Soc. Faraday Trans. 90, 1065-1072.
28. 3Σg transition in molecular oxygen: a Fourier transform near-infrared luminescence study. J. Phys. Chem. 99, 17586-17592.
29. +) in solution phase. J. Phys. Chem. A 101, 8581-8586.
30. 2. J. Phys. Chem, 100, 8049-8052.
31. Lin, S. H., J. Lewis and T. A. Moore (1991) Application of the collision complex model to the photophysical processes of singlet oxygen in liquids. J. Photochem. Photobiol. A Chem. 56, 25-34.
32. 3Σg ) states of molecular oxygen. J. Phys. Chem. A 102, 8970-8973.
33. - transition in molecular oxygen: interpretation of solvent effects on spectral shifts. J. Phys. Chem. A. 103, 3418-3422.
34. Kasha, M. and D. E. Brabham (1979) Singlet oxygen electronic structure and photosensitization. In Singlet Oxygen (Edited by H. H. Wasserman and R. W. Murray), pp. 1-33. Academic Press, New York.
35. Mikkelsen, K. V., H. Ågren, H. J. A. Jensen and T. Helgaker (1988) A multiconfigurational self-consistent reaction-field method. J. Chem. Phys. 89, 3086-3095.
36. Mikkelsen, K. V., A. Cesar, H. Ågren and H. J. A. Jensen (1995) Multiconfigurational self-consistent reaction field the-ory for nonequilibrium solvation. J. Chem. Phys. 103, 9010-9023.
37. Strickler, S. J. and R. A. Berg (1962) Relationship between absorption intensity and fluorescence lifetime of molecules. J. Chem. Phys. 37, 814-822.
38. Poulsen, T. D., P. R. Ogilby and K. V. Mikkelsen (1999) Quadratic response of molecules in a nonequilibrium and equilibrium solvation model: generalizations to include both singlet and triplet perturbations. J. Chem. Phys. 111, 2678-2685.
39. - transition in oxygen. Chem. Phys. Lett. 215, 477-482.
40. Losev, A. P., I. N. Nichiporovich, I. M. Byteva, N. N. Drozdov and I. F. Al Jghgami (1991) The perturbing effect of solvents on the luminescence rate constant of singlet molecular oxygen. Chem. Phys. Lett. 181, 45-50.
41. 1Δg). J. Phys. Chem. 93, 4691-4692.
42. 1Δg), in organic and aqueous media. J. Am. Chem. Soc. 109, 3091-3097.
43. -) radiative transition: comments regarding charge-transfer interactions. J. Phys. Chem. A 102, 9829-9832.
44. 1Δg oxygen. J. Mol. Struct. (Theochem.) 183, 207-214.
45. Minaev, B. F., S. Lunell and G. I. Kobzev (1993) The influence of intermolecular interaction on the forbidden near-IR transitions in molecular oxygen. J. Mol. Struct. (Theochem.) 284, 1-9.
46. - transition probabilities in molecular oxygen. J. Chem. Soc. Faraday Trans. 93, 2231-2239.
47. 1Δg) in the gas phase. Int. J. Quant. Chem. 39, 287-298.
48. Gorman, A. A. and M. A. J. Rodgers (1989) Singlet oxygen. In Handbook of Organic Photochemistry, Vol. 2 (Edited by J. C. Scaiano), pp. 229-247. CRC Press, Boca Raton, FL.
49. Monroe, B. M. (1985) Singlet oxygen in solution: lifetimes and reaction rate constants. In Singlet Oxygen, Vol. 1 (Edited by A. A. Frimer), pp. 177-224. CRC Press, Boca Raton, FL.
50. Hurst, J. R. and G. B. Schuster (1983) Nonradiative relaxation of singlet oxygen in solution. J. Am. Chem. Soc. 105, 5756-5760.
51. Rodgers, M. A. J. (1983) Solvent-induced deactivation of singlet oxygen: additivity relationships in nonaromatic solvents. J. Am. Chem. Soc. 105, 6201-6205.
52. Schmidt, R. and H.-D. Brauer (1987) Radiationless deactivation of singlet oxygen by solvent molecules. J. Am. Chem. Soc. 109, 6976-6981.
53. 2 in solution. J. Phys. Chem. A 102, 4769-4774.
54. Tsubomura, H. and R. S. Mulliken (1960) Molecular complexes and their spectra. XII. Ultraviolet absorption spectra caused by the interaction of oxygen with organic molecules. J. Am. Chem. Soc. 82, 5966-5974.
55. Kawaoka, K., A. U. Khan and D. R. Kearns (1967) Role of singlet excited stales of molecular oxygen in the quenching of organic triplet states. J. Chem. Phys. 46, 1842-1853.
56. -)-organic molecule charge-transfer absorption band. J. Phys. Chem. 93, 5493-5500.
57. 1Δg) production in photoexcited organic molecule - molecular oxygen complexes. J. Phys. Chem. 95, 5190-5197.
58. Clennan, E. L., L. J. Noe, E. Szneler and T. Wen (1990) Hydrazines: new charge-transfer physical quenchers of singlet oxygen. J. Am. Chem. Soc. 112, 5080-5085.
59. Young, R. H., R. L. Martin, D. Feriozi, D. Brewer and R. Kayser (1973) On the mechanism of quenching of singlet oxygen by amines - III. Evidence for a charge-transfer-like complex. Photochem. Photobiol. 17, 233-244.
60. Thomas, M. J. and C. S. Foote (1978) Chemistry of singlet oxygen - XXVI. Photooxygenation of phenols. Photochem. Photobiol. 27, 683-693.
61. Kuriyama, Y., P. R. Ogilby and K. V. Mikkelsen (1994) Solvent effects on the oxygen-organic molecule charge-transfer absorption. J. Phys. Chem. 98, 11918-11923.
62. +) in solution. J. Am. Chem. Soc. 118, 388-392.
63. 1Δg) in solution. J. Phys. Chem. 100, 17226-17231.
64. Foote, C. S. (1994) Photophysical and photochemical properties of fullerenes. Top. Curr. Chem. 169, 347-363.
65. Hung, R. R. and J. i. Grabowski (1991) A precise determination of the triplet energy of C60 by photoacoustic calorimetry. J. Phys. Chem. 95, 6073-6075.
66. Terazima, M., N. Hirota, H. Shinohara and Y. Saito (1991) Photothermal investigation of the triplet state of C60. J. Phys. Chem. 95, 9080-9085.
67. Foote, C. S. and R. W. Denny (1968) Chemistry of singlet oxygen. VII. Quenching by beta-carotene. J. Am. Chem. Soc. 90, 6233-6235.
68. Farmilo, A. and F. Wilkinson (1973) On the mechanism of quenching of singlet oxygen in solution. Photochem. Photobiol. 18, 447-450.
69. Conn, P. F., W. Schalen and T. G. Truscott (1991) The singlet oxygen and carotenoid interaction. J. Photochem. Photobiol. B Biol. 11, 41-47.
70. Frimer, A. A. (1985) Singlet Oxygen. CRC Press, Boca Raton, FL.
71. Khan, A. U. and D. R. Kearns (1968) Generation and reactions of singlet sigma and singlet delta oxygen molecules in sensitized photooxygenations. Adv. Chem. Ser. 77, 143-165.
72. Kearns, D. R., R. A. Hollins, A. U. Khan, R. W. Chambers and P. Radlick (1967) Evidence for the participation of singlet sigma and singlet delta oxygen in dye-sensitized photooxygenation reactions. I. J. Am. Chem. Soc. 89, 5455-5456.
73. Kearns, D. R., R. A. Hollins, A. U. Khan and P. Radlick (1967) Evidence for the participation of singlet sigma and singlet delta oxygen in dye-sensitized photooxygenation reactions. II. J. Am. Chem. Soc. 89, 5456-5457.
74. Reddy, K. V. and M. J. Berry (1978) Intracavity dye laser photoactivation of chemical reactions. J. Opt. Soc. Am. 68, 694.
75. Kearns, D. R. (1971) Physical and chemical properties of singlet molecular oxygen. Chem. Rev. 71, 395-427.
76. +). J. Phys. Chem. A 101, 5672-5677.
77. Birks, J. B. (1970) Photophysics of Aromatic Molecules. Wiley-Interscience, London.
78. Gijzeman, O. L. J., F. Kaufman and G. Porter (1973) Oxygen quenching of aromatic triplet states in solution. Part 1. J. Chem. Soc. Faraday Trans. II 69, 708-720.
79. Gijzeman, O. L. J. and F. Kaufman (1973) Oxygen quenching of aromatic triplet states in solution. Part 2. J. Chem. Soc. Faraday Trans. II 69, 721-726.
80. Saltiel, J. and B. W. Atwater (1988) Spin-statistical factors in diffusion-controlled reactions. Adv. Photochem. 14, 1-90.
81. Wilkinson, F., D. J. McGarvey and A. F. Olea (1993) Factors governing the efficiency of singlet oxygen production during oxygen quenching of singlet and triplet states of anthracene derivatives in cyclohexane solution. J. Am. Chem. Soc. 115, 12144-12151.
82. Redmond, R. W. and S. E. Braslavsky (1988) Time-resolved thermal lensing and phosphorescence studies on photosensitized singlet molecular oxygen formation. Influence of the electronic configuration of the sensitizer on sensitization efficiency. Chem. Phys. Lett. 148, 523-529.
83. McLean, A. J. and M. A. J. Rodgers (1993) Variable-temperature study of aromatic hydrocarbon triplet-state quenching by molecular oxygen in solution. J. Am. Chem. Soc. 115, 4786-4792.
84. Grewer, C. and H.-D. Brauer (1994) Mechanism of the triplet-state quenching by molecular oxygen in solution. J. Phys. Chem. 98, 4230-4235.
85. Nau, W. M. and J. C. Scaiano (1996) Oxygen quenching of excited aliphatic ketones and diketones. J. Phys. Chem. 100, 11360-11367.
86. Darmanyan, A. P. and C. S. Foote (1993) Definition of the nature of ketone triplet states on the basis of singlet oxygen generation efficiency. J. Phys. Chem. 97, 4573-4576.
87. Kearns, D. R. and A. U. Khan (1969) Sensitized photooxygenation reactions and the role of singlet oxygen. Photochem. Photobiol. 10, 193-210.
88. + in solution phase photosensitized reactions. J. Phys. Chem. 97, 9593-9598.
89. 2 by triplet states. Chem. Phys. Lett. 221, 7-14.
90. + in solution phase photosensitized reactions. 2. Effects of sensitizer substituent. J. Photochem. Photobiol. A Chem. 90, 85-89.
91. Nau, W. M., W. Adam and J. C. Scaiano (1996) Singlet oxygen production from excited azoalkanes. J. Am. Chem. Soc. 118, 2742-2743.
92. Kearns, D. R. (1969) Selection rules for singlet-oxygen reactions. Concerted addition reactions. J. Am. Chem. Soc. 91, 6554-6563.
93. Schmidt, R., W. Drews and H.-D. Brauer (1980) Photolysis of the endoperoxide of heterocoerdianthrone. A concerted, adiabatic cycloreversion originating from an upper excited singlet state. J. Am. Chem. Soc. 102, 2791-2797.
94. 1Δg). J. Chem. Phys. 44, 2529-2530.
95. +) in discharge flow systems. Trans. Faraday Soc. 67, 2036-2043.
96. Krasnovsky, A. A. and C. S. Foote (1993) Time-resolved measurements of singlet oxygen dimol-sensitized luminescence. J. Am. Chem. Soc. 115, 6013-6016.
97. Gorman, A. A., I. Hamblett and T. J. Hill (1995) Evidence against "dimol-sensitized luminescence" in solutions containing singlet oxygen. J. Am. Chem. Soc. 117, 10751-10752.
98. 1Δg) dimol-sensitized luminescence in solution. J. Am. Chem. Soc. 120, 4883-4884.
99. Arnold, S. J., E. A. Ogryzlo and H. Witzke (1964) Some new emission bands of molecular oxygen. J. Chem. Phys. 40, 1769-1770.
100. Khan, A. U. and M. Kasha (1970) Chemiluminescence arising from simultaneous transitions in pairs of singlet oxygen molecules. J. Am. Chem. Soc. 92, 3293-3300.
101. Krasnovsky, A. A. and K. V. Neverov (1990) Photoinduced dimol luminescence of singlet molecular oxygen in solutions of photosensitizers. Chem. Phys. Lett. 167, 591-596.
102. 2. J. Phys. Chem. A 103, 2599-2605.