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Photochemical Techniques and the Photodimerization of Anthracene and Related Compounds

  • Dwaine O. Cowan
  • Ronald L. Drisko

Abstract

In this chapter we will endeavor to answer the following questions: What does the photochemist do in preparing to investigate the photochemical behavior of a molecule? What equipment does he use to carry out his experiments? Once he has determined the results of the reaction, how can he develop a mechanism to account for these results? In answering these questions we will be concerned mainly with the photochemistry of anthracene and related compounds.

Keywords

Quantum Yield Lower Unoccupied Molecular Orbital Fluorescence Lifetime Photochemical Reaction Fluorescence Quantum Yield 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    C.A. Coulson and A. Streitweiser, Jr., Dictionary of-π-Electron Calculations, Freeman, San Francisco (1965), pp. 29–30.Google Scholar
  2. 2.
    H. H. Jaffe and M. Orchin, Theory and Application of Ultraviolet Spectroscopy, Wiley, New York (1962), p. 216.Google Scholar
  3. 3.
    E. W. Thulstrup, J. Michl, and J. H. Eggers, J. Phys. Chem. 74, 3868 (1970).CrossRefGoogle Scholar
  4. 4.
    G. Weber, Biochem. J. 75, 335 (1960).Google Scholar
  5. 5.
    C. A. Parker, Photoluminescence of Solutions, Elsevier, New York (1968).Google Scholar
  6. 6.
    W. R. Ware, in Creation and Detection of the Excited State, A. Lamola, ed., Marcel Dekker, New York (1971).Google Scholar
  7. 7.
    A. S. Cherkasov, V. A. Molchanov, T. M. Vember, and K. G. Voldaikina, Sov. Phys.—Doklady 1, 427 (1956).Google Scholar
  8. 8.
    R. Shon, D. O. Cowan, and W. Schmiegel, J. Phys. Chem. 79, 2087 (1975).CrossRefGoogle Scholar
  9. 9.
    J. Fritzsche, J. Prakt. Chem. 101, 333 (1867); 106, 274 (1869).CrossRefGoogle Scholar
  10. 10. (a)
    K. Ellis, J. Prakt. Chem. 44, 467 (1891)CrossRefGoogle Scholar
  11. (b).
    W. Orndorff and F. Cameron, Amer. Chem. J. 17, 658 (1895).CrossRefGoogle Scholar
  12. 11.
    J. Houben, Das Anthracen und die Anthrachinone, Verlag, Leipzig (1929), p. 135.Google Scholar
  13. 12.
    C. Linebarger, Amer. Chem. J. 14, 597 (1892).Google Scholar
  14. 13.
    C. A. Coulson, L. E. Orgel, W. Taylor, and J. Weiss, J. Chem. Soc., 2961 (1955).Google Scholar
  15. 14.
    M. Ehrenberg, Acta Cryst. 20, 177 (1966).CrossRefGoogle Scholar
  16. 15.
    R. Calas and R. Lalande, Bull. Soc. Chim. Fr., 763 (1959).Google Scholar
  17. 16.
    R. Lalande and R. Calas, Bull. Soc. Chim. Fr., 766 (1959).Google Scholar
  18. 17.
    R. Lalande and R. Calas, Bull. Soc. Chim. Fr., 144 (1960).Google Scholar
  19. 18.
    R. Calas, R. Lalande, and P. Mauret, Bull. Soc. Chim. Fr., 148 (1960).Google Scholar
  20. 19.
    R. Calas, R. Lalande, J.-G. Faugere, and F. Moulines, Bull. Soc. Chim. Fr., 119, 121 (1965).Google Scholar
  21. 20.
    D. E. Applequist, E. C. Friedrich, and M. T. Rogers, J. Amer. Chem. Soc. 81, 457 (1959).CrossRefGoogle Scholar
  22. 21.
    D. E. Applequist, R. L. Little, E. C. Friedrich, and R. E. Wall, J. Amer. Chem. Soc. 81, 452 (1959).CrossRefGoogle Scholar
  23. 22.
    O. C. Chapman and K. Lee, J. Org. Chem. 34, 4166 (1969).CrossRefGoogle Scholar
  24. 23.
    R. Lalande and R. Calas, Bull Soc Chim. Fr., 770 (1959).Google Scholar
  25. 24.
    T. M. Vember and A. S. Cherkasov, Opt. Spectrosc. 6, 148 (1959).Google Scholar
  26. 25.
    T. M. Vember, Opt. Spectrosc. 20, 188 (1966).Google Scholar
  27. 26.
    R. Lapouyade, A. Castellan, and H. Bouas-Laurent, C. R. Acad. Sci. (Paris) C 268, 217 (1969).Google Scholar
  28. 27.
    H. Bouas-Laurent and R. Lapouyade, Chem. Comm., 817 (1969).Google Scholar
  29. 28.
    F. D. Greene, S. C. Misrock, and J. R. Wolfe, J. Amer. Chem. Soc. 77, 3852 (1955).CrossRefGoogle Scholar
  30. 29.
    D. E. Applequist, T. L. Brown, J. P. Kleiman, and S. T. Young, Chem. Ind. (London), 850 (1959).Google Scholar
  31. 30.
    F. D. Greene, Bull. Soc. Chim. Fr., 1365 (1960).Google Scholar
  32. 31.
    I. Roit and W. Waters, J. Chem. Soc., 2695 (1952).Google Scholar
  33. 32.
    W. Henderson, Doctoral Thesis, University of Minnesota (1962).Google Scholar
  34. 33.
    R. Livingston and K. S. Wei, J. Amer. Chem. Soc. 89, 3098 (1967).CrossRefGoogle Scholar
  35. 34.
    L. Kaminski, Doctoral Thesis, Massachusetts Institute of Technology (1959).Google Scholar
  36. 35.
    D. E. Applequist, M. A. Lintner, and R. Searle, J. Org. Chem. 33, 254 (1968).CrossRefGoogle Scholar
  37. 36.
    J. H. Golden, J. Chem. Soc., 3741 (1961).Google Scholar
  38. 37.
    N. S. Weinshenker and F. D. Greene, J. Amer. Chem. Soc. 90, 506 (1968).CrossRefGoogle Scholar
  39. 38.
    R. Lapouyade, A. Castellan, and H. Bouas-Laurent, Tetrahedron Lett., 3537 (1969).Google Scholar
  40. 39.
    H. Bouas-Laurent and A. Castellan, Chem. Comm., 1648 (1970).Google Scholar
  41. 40.
    A. Schonberg, A. Mustafa, M. Z. Barakat, N. Latif, R. Moubasher, and A. Mustafa, J. Chem. Soc., 2126 (1948).Google Scholar
  42. 41.
    J. B. Birks, J. H. Appleyard, and R. Pope, Photochem. Photobiol. 2, 493 (1963).CrossRefGoogle Scholar
  43. 42.
    J. S. Bradshaw and G. S. Hammond, J. Amer. Chem. Soc. 85, 3953 (1963).CrossRefGoogle Scholar
  44. 43.
    P. Wilanat and B. K. Selinger, Austral. J. Chem. 21, 733 (1968).CrossRefGoogle Scholar
  45. 44.
    J. S. Bradshaw, N. B. Nielsen, and D. P. Rees, J. Org. Chem. 33, 259 (1968).CrossRefGoogle Scholar
  46. 45.
    T. W. Mattingly, Jr., J. E. Lancaster, and A. Zweig, Chem. Comm., 595 (1971).Google Scholar
  47. 46. (a)
    E. C. Taylor and W. W. Paudler, Tetrahedron Lett., 25, 1 (1960)CrossRefGoogle Scholar
  48. (b).
    W. A. Ayer, R. Hoyatsu, P. DeMayo, S. T. Reid, and J. B. Stothers, Tetrahedron Lett., 648 (1961)Google Scholar
  49. (c).
    G. Slomp, F. A. Mackiller, and L. A. Paquette, J. Amer. Chem. Soc. 83, 4472 (1961).CrossRefGoogle Scholar
  50. 47.
    E. C. Taylor and R. O. Kan, J. Amer. Chem. Soc. 85, 776 (1963).CrossRefGoogle Scholar
  51. 48.
    P. DeMayo and R. W. Yip, Proc. Chem. Soc. 84 (1964).Google Scholar
  52. 49.
    N. C. Yang and J. Libman, J. Amer. Chem. Soc. 94, 1405 (1972).CrossRefGoogle Scholar
  53. 50.
    N. C. Yang, J. Libman, L. Barrett, Jr., M. H. Hui, and R. L. Loeschin, J. Amer. Chem. Soc. 94, 1406 (1972).CrossRefGoogle Scholar
  54. 51. (a)
    W. G. Leighton and G. S. Forbes, J. Amer. Chem. Soc. 52, 3139 (1930)CrossRefGoogle Scholar
  55. (b).
    G. S. Forbes, G. B. Kistiakowsky, and L. J. Heidt, J. Amer. Chem. Soc. 54, 3246 (1932)CrossRefGoogle Scholar
  56. (c).
    F. P. Brackett, Jr., and G. S. Forbes, J. Amer. Chem. Soc. 55, 4459 (1933)CrossRefGoogle Scholar
  57. (d).
    B. M. Norton, J. Amer. Chem. Soc. 56, 2294 (1934)CrossRefGoogle Scholar
  58. (e).
    C. A. Discher, P. E. Smith, I. Lippman, and R. Turse, J. Phys. Chem. 67, 2501 (1963).CrossRefGoogle Scholar
  59. 52.
    J. N. Pitts, Jr., J. D. Margerum, R. P. Taylor, and W. Brim, J. Amer. Chem. Soc. 77, 5499 (1955).CrossRefGoogle Scholar
  60. 53.
    D. A. Volman and J. R. Seed, J. Amer. Chem. Soc. 86, 1879 (1940).Google Scholar
  61. 54. (a)
    C. G. Hatchard and C. A. Parker, Proc Roy. Soc. (London) A 235, 58 (1956)CrossRefGoogle Scholar
  62. (b).
    Baxendate and Bridge, J. Phys. Chem. 59, 783 (1955)CrossRefGoogle Scholar
  63. (c).
    J. Lee and H. H. Seliger, J. Chem. Phys. 40, 519 (1964)CrossRefGoogle Scholar
  64. (d).
    E. E. Wegner and A. W. Adamson, J. Amer. Chem. Soc. 88, 394 (1966).CrossRefGoogle Scholar
  65. 55. (a)
    R. N. Smith, P. A. Leighton, and W. G. Leighton, J. Amer. Chem. Soc. 61, 2299 (1939)CrossRefGoogle Scholar
  66. (b).
    L. B. Thomas, J. Amer. Chem. Soc. 62, 1879 (1940).CrossRefGoogle Scholar
  67. 56.
    E. J. Bowen, Disc. Faraday Soc. 14, 143 (1953).CrossRefGoogle Scholar
  68. 57.
    E. J. Bowen and N. Norton, Trans. Faraday Soc. 35, 44 (1939).CrossRefGoogle Scholar
  69. 58.
    E. J. Bowen, Trans. Faraday Soc. 42, 133 (1946).CrossRefGoogle Scholar
  70. 59.
    E. J. Bowen, Trans. Faraday Soc. 50, 97 (1954).CrossRefGoogle Scholar
  71. 60.
    E. J. Bowen and D. W. Tarner, Trans. Faraday Soc. 51, 475 (1955).CrossRefGoogle Scholar
  72. 61.
    A. S. Cherkasov and T. M. Vember, Opt. Spektrosk. 4, 203 (1958).Google Scholar
  73. 62.
    A. S. Cherkasov and T. M. Vember, Opt. Spectrosc. 6, 319 (1959).Google Scholar
  74. 63.
    W. W. Schmiegel, Doctoral Thesis, The Johns Hopkins University (1970).Google Scholar
  75. 64.
    D. O. Cowan and W. W. Schmiegel, Angew. Chem. (Intern. Ed.) 10, 517 (1971).CrossRefGoogle Scholar
  76. 65.
    D. O. Cowan and W. W. Schmiegel, J. Amer. Chem. Soc. 94, 6779 (1972).CrossRefGoogle Scholar
  77. 66. (a)
    G. W. Robinson and R. P. Frosch, J. Chem. Phys. 37, 1962 (1962)CrossRefGoogle Scholar
  78. (b).
    G. W. Robinson and R. P. Frosch, J. Chem. Phys. 38, 1187 (1963)CrossRefGoogle Scholar
  79. (c).
    M. A. El-Sayed, J. Chem. Phys. 38, 2834 (1963)CrossRefGoogle Scholar
  80. (d).
    T. Medinger and F. Wilkinson, Trans. Faraday Soc. 61, 620 (1965).CrossRefGoogle Scholar
  81. 67.
    R. S. Livingston, in Photochemistry in the Liquid and Solid State, F. Daniels, ed., Wiley, New York (1960), pp. 76–86.Google Scholar
  82. 68.
    T. Forster, in Proceedings of the International Conference on Luminescence, Vol. 1, G. Szigett, ed., Akademiai Kiado, Budapest (1968), pp. 160–165.Google Scholar
  83. 69.
    B. Stevens and M. I. Ban, Trans. Faraday Soc. 66, 1515 (1964).CrossRefGoogle Scholar
  84. 70.
    T. Forster and K. Kasper, Z. Physik. Chem. (Frankfurt) 1, 275 (1964).CrossRefGoogle Scholar
  85. 71.
    J. B. Birks and J. B. Aladekome, Photochem. Photobiol. 2, 415 (1963).CrossRefGoogle Scholar
  86. 72.
    T. Azumi, A. T. Armstrong, and S. P. McGlynn, J. Chem. Phys. 41, 3839 (1964).CrossRefGoogle Scholar
  87. 73.
    J. B. Birks and L. G. Christophorou, Proc. Roy. Soc. (London) A 274, 552 (1963).CrossRefGoogle Scholar
  88. 74.
    J. B. Birks, D. S. Dyson, and T. A. King, Proc. Roy. Soc. (London) A 277, 270 (1965).CrossRefGoogle Scholar
  89. 75.
    B. Stevens, Spectrochim. Acta 18, 439 (1962).CrossRefGoogle Scholar
  90. 76.
    E. Chandross and J. Ferguson, J. Chem. Phys. 45, 3560 (1966).Google Scholar
  91. 77.
    T. C. Werner and D. M. Hercules, J. Phys. Chem. 73, 2005 (1969); 74, 1030 (1970).CrossRefGoogle Scholar
  92. 78. (a)
    D. Evans, J. Chem. Soc. 1351, (1957)Google Scholar
  93. (b).
    G. N. Lewis and M. Kasha, J. Amer. Chem. Soc. 66, 2100 (1944).CrossRefGoogle Scholar
  94. 79.
    D. S. McClure, J. Chem. Phys. 17, 905 (1949).CrossRefGoogle Scholar
  95. 80.
    J. W. Hilpern, G. Porter, and C. J. Stief, Proc. Roy. Soc. A 277, 437 (1964).CrossRefGoogle Scholar
  96. 81.
    A. S. Cherkasov and T. M. Vember, Opt. Spectrosc. 7, 207 (1959).Google Scholar
  97. 82.
    R. Livingston and V. S. Rao, J. Phys. Chem. 63, 794 (1959).CrossRefGoogle Scholar
  98. 83.
    E. J. Bowen, in Advances in Photochemistry, Vol. 1, W. A. Noyes, Jr., G. S. Hammond, and J. N. Pitts, Jr., eds., Interscience, New York (1963), p. 23.CrossRefGoogle Scholar
  99. 84.
    K. Gollnich and G. O. Schenck, in 1,4-Cycloaddition Reactions, J. Hamer, ed., Academic Press, New York (1967).Google Scholar
  100. 85.
    C. S. Foote and S. Wexler, J. Amer. Chem. Soc. 86, 3879, 3880 (1964).CrossRefGoogle Scholar
  101. 86.
    C. S. Foote, S. Wexler, W. Ando, and R. Higgins, J. Amer. Chem. Soc. 90, 975 (1968).CrossRefGoogle Scholar
  102. 87.
    S. N. Foner and R. L. Hudson, J. Chem. Phys. 23, 1974 (1955); 25, 601 (1956).CrossRefGoogle Scholar
  103. 88.
    E. J. Corey and W. C. Taylor, J. Amer. Chem. Soc., 3881 (1964).Google Scholar
  104. 89. (a)
    H. Kautsky and H. deBruijn, Naturwiss. 19, 1043 (1931)CrossRefGoogle Scholar
  105. (b).
    H. Kautsky, H. deBruijn, R. Neuwirth, and W. Baumeister, Ber. Deut. Chem. Ges. 66, 1588 (1933)CrossRefGoogle Scholar
  106. (c).
    H. Kautsky, Biochem. 2, 271, 291 (1937).Google Scholar
  107. 90.
    H. Gaffron, Biochem. Z. 287, 130 (1936).Google Scholar
  108. 91.
    R. Maleski and H. Morrison, Mol. Photochem. 4, 507 (1972).Google Scholar

Copyright information

© Plenum Press, New York 1976

Authors and Affiliations

  • Dwaine O. Cowan
    • 1
  • Ronald L. Drisko
    • 2
  1. 1.The Johns Hopkins UniversityBaltimoreUSA
  2. 2.Essex Community CollegeBaltimoreUSA

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