Photochemie pp 605-641 | Cite as

Photochromie und reversible Photoisomerisierung

  • Ernst Fischer
Conference paper
Part of the Fortschritte der Chemischen Forschung book series (TOPCURRCHEM, volume 7)


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  1. 1.
    Anderson, D. G., and G. Wettermark: Photoinduced Isomerization in Anils. J. Amer. chem. Soc. 87, 1433 (1965).CrossRefGoogle Scholar
  2. 2.
    Bergmann, E. D., E. Fischer et Y. Hirshberg: Un Cas d'isomerie cis-trans dans la Série du Dibenzofulvene. Bull. Soc. chim. France 17, 1103 (1950).Google Scholar
  3. 3.
    Bercovici, T., and E. Fischer: Photochromismin Spiropyrans. Part VI. To be published.Google Scholar
  4. 4.
    --: Photosensitized Coloration of Photochromic Spiropyrans. J. Amer. chem. Soc. 86, 5687 (1964).CrossRefGoogle Scholar
  5. 5.
    --Unpublished Results.Google Scholar
  6. 6.
    Brockmann, H., u. R. Mühlmann: Über die photochemische Cyclisierung des Helianthrons und Dianthrons. Chem. Ber. 82, 348 (1949).Google Scholar
  7. 7.
    Burawoy, A., and A. R. Thompson: The Effect of Solvents on the Tautomeric Equilibria of 4-Arylazo-1-Naphthols and the ortho-Effect. J. chem. Soc. [London] 1953, 1443.Google Scholar
  8. 8.
    Cohen, M. D., Y. Hirshberg, and G. M. J. Schmidt: The Phototropy of Anils. Hydrogen Bonding, p. 293. Ed. Hadzi. London: Pergamon Press 1959.Google Scholar
  9. 9.
    ---The Photoactivity of Anils of Salicylaldehydes in Rigid Solutions. J. chem. Soc. [London] 1964, 2051.Google Scholar
  10. 10.
    ---The Effect of Solvent, Temperature, and Light on the Structure of Anils of Hydroxynaphthaldehydes. J. chem. Soc. [London] 1964, 2060.Google Scholar
  11. 11.
    Cundall, R. B., and P. A. Griffiths: Olefins as Triplet-state Scavengers in Irradiated Systems. Chem. Comm. 1966, 194.Google Scholar
  12. 12.
    Dessauer, R., and J. P. Paris: Photochromism. Advances in Photochemistry, Vol. I, p. 275. Ed. W. A. Noyes, G. S. Hammond, and J. N. Pitts jr. Interscience.Google Scholar
  13. 13.
    Fischer, E., and Y. F. Frei: Photoisomerization involving the C-N Double Bond. J. chem. Phys. 27, 808 (1957).CrossRefGoogle Scholar
  14. 14.
    -, M. Frankel, and R. Wolovsky: Wavelength Dependence of Photoisomerization Equilibria in Azocompounds. J. chem. Phys. 23, 1367 (1955).CrossRefGoogle Scholar
  15. 15.
    -To be published.Google Scholar
  16. 16.
    -, and M. Kaganowich: Photoisomerization and Possible Geometrical Isomerism in Quinoid Systems. Bull. Res. Council Israel A 10, 138 (1961).Google Scholar
  17. 17.
    -The Calculation of Photostationary States in Systems AB when only A is known. To be published.Google Scholar
  18. 18.
    -: Temperature Dependence of Photoisomerization: Azobenzene and the Azonaphthalenes. J. Amer. chem. Soc. 82, 3249 (1960).CrossRefGoogle Scholar
  19. 19.
    -, and Y. F. Frei: Photoisomerization Equilibria in Azodyes. J. chem. Phys. 27, 328 (1957).CrossRefGoogle Scholar
  20. 20.
    --Tautomerism and Geometrical Isomerism of Arylazo-phenols and naphthols. 4-Phenylazo-1-Naphthol. J. chem. Soc. [London] 1953, 3159.Google Scholar
  21. 21.
    -, G. Grabor, Y. F. Frei, D. Gegion, and M. Kaganowich: To be published.Google Scholar
  22. 22.
    -Unpublished results with the anil of 2-Hydroxy-3-Naphthaldehyde.Google Scholar
  23. 23.
    Fischer, G., and E. Fischer: Photosensitized Isomerization of Azobenzene. To be published.Google Scholar
  24. 24.
    Fischer, E., H. P. Lehmann, and G. Stein: X-and Gamma-Ray Induced Radiolytic Isomerization of Solutions of Stilbene. J. chem. Phys. 45, 3905 (1966).CrossRefGoogle Scholar
  25. 25.
    Fischer, G., E. Fischer, and G. Stein: Temperature Dependence of Radiolytic Isomerisation in Liquid and Solid Aromatic Solvents. To be published.Google Scholar
  26. 26.
    Frankel, M., R. Wolovsky, and E. Fischer: Geometrical Isomerism of the Azonaphthalenes. J. chem. Soc. [London] 1955, 3441.Google Scholar
  27. 27.
    Gabor, G., and E. Fischer: 2-Phenylazo-3-Naphthol. The Effect of Internal Hydrogen Bonds on Photoisomerization. J. phys. Chem. 66, 2478 (1962).Google Scholar
  28. 28a.
    Gegiou, D., and E. Fischer: Temperature Dependence of Photoisomerization: Sterically Hindered Stilbene and Azobenzene Derivatives. To be published.Google Scholar
  29. 28b.
    -Temperature Dependence of Photoisomerization: Effects of Substituents and of Viscosity. To be published.Google Scholar
  30. 29.
    Garlick, G. F. J.: Some Physical Aspects of Energy Transfer in Radiation Processes, S. 93. Ed. G. O. Phillips. London: Elsevier 1966.Google Scholar
  31. 30.
    Greenspan, H., and E. Fischer: Viscosity of Glass-forming Solvent Mixtures at Low Temperatures. J. phys. Chem. 69, 2466 (1965).Google Scholar
  32. 31.
    Hirshberg, Y.: Photochromie dans la Serie de la Bianthrone. Compt. rend. 231, 903 (1950).Google Scholar
  33. 32.
    -, and E. Fischer: Absorption Measurements and Irradiations in the Cary and Beckman Spectrophotometers at low and high Temperatures. Rev. Sci. Inst. 30, 197 (1959).CrossRefGoogle Scholar
  34. 33.
    --Low-Temperature Photochromism and its relation to Thermochromism. J. chem. Soc. [London] 1953, 629.Google Scholar
  35. 34.
    --Photochromism and Reversible Multiple Internal Transitions in Some Spiropyrans at Low Temperatures. Part I. J. chem. Soc. [London] 1954, 297.Google Scholar
  36. 35.
    -: Reversible Formation and Eradication of Colors by Irradiation at Low Temperatures. A Photochemical Memory Model. J. Amer. chem. Soc. 78, 2304 (1956).CrossRefGoogle Scholar
  37. 36.
    -, E. H. Frei, and E. Fischer: Reversible Appearance and Disappearance of Coloured Modifications of Some Compounds as a Result of Irradiation at Low Temperatures. J. chem. Soc. [London] 1953, 2184.Google Scholar
  38. 37.
    -, and E. Fischer: Photochromism in Spiropyrans. Part II. J. chem. Soc. [London] 1954, 3129.Google Scholar
  39. 38.
    -: Formation of Reversible Colored Modifications at Low Temperatures by Bombardment with Electrons. J. chem. Phys. 27, 758 (1957).CrossRefGoogle Scholar
  40. 39.
    -: Photochromism Induced by Gamma Rays. Bull. Res. Council Israel A 7, 228 (1958).Google Scholar
  41. 40.
    Hammond, G. S., J. Saltiel, A. A. Lamola, N. J. Turro, J.S. Bradshaw, D. O. Cowan; R. C. Counsell, V. Vogt and C. Dalton: Mechanism of Photochemical Reactions in Solution. XXII. Photochemical cis-trans Iso-merization. J. Amer. chem. Soc. 86, 3197 (1964).CrossRefGoogle Scholar
  42. 41a.
    Heiligman-Rim, R., Y, Hirshberg, and E. Fischer: Photochromism in Spiropyrans. Part III. The Extent of Phototransformation. J. chem. Soc. [London] 1961, 156.Google Scholar
  43. 41b.
    ---: Photochromism in Spiropyrans. Part IV. Evidence for the Existence of Several Forms of the Coloured Modification. J. phys. Chem. 66, 2465 (1962).Google Scholar
  44. 42.
    ---: Photochromism in Spiropyrans. Part V. The Mechanism of Phototransformation. J. phys. Chem. 66, 2470 (1962).Google Scholar
  45. 43.
    -, T. Bercovici, and E. Fischer: Cations of the Spiropyran-Merocyanine System and their Photochromic Properties. Lecture at the Symposium on Photochemistry, Rochesters, 1963.Google Scholar
  46. 44.
    Kortüm, G., u. G. Bayer: Zur Thermochromie und Photochromie der Dehydrodianthrone. Ber. Bunsenges. physik. Chemie 67, 24 (1963).Google Scholar
  47. 45.
    Kuhn, R., u. F. Baer: Über die Konstitution der Oxy-azo-Verbindungen. Ann. Chem. 516, 143 (1935).Google Scholar
  48. 46.
    Lehmann, H. P., G. Stein, and E. Fischer: Sensitized Radiolytic Isomerization of Stilben: Chem. Comm. 1965, 583.Google Scholar
  49. 47.
    Für die Klärung dieser Möglichkeiten sind wir Herrn Prof. E. Lippert zu Dank verpflichtet.Google Scholar
  50. 48.
    Lippert, E., D. Samuel u. E. Fischer: Infrarot-und 17O-NMR-Spektren und Struktur einiger Isomerer o-Arylazonaphthole. Ber. Bunsenges. physik. Chemie 69, 155 (1965).Google Scholar
  51. 49.
    Malkin, Sh., and E. Fischer: Temperature Dependence of Photoisomerization: Quantum Yields of cis-trans Isomerizations in Azocompounds. J. phys. Chem. 66, 2482 (1962).Google Scholar
  52. 50.
    --: Temperature Dependence of Photoisomerization: Direct and Sensitized Photoisomerization of Stilbenes. J. phys. Chem. 68, 1153 (1964).Google Scholar
  53. 51.
    -: Photoisomerization of Stilbene by Means of Direct and Indirect Excitation. Bull. Res. Council Israel A 11, 208 (1962).Google Scholar
  54. 52.
    Muszkat, K. A., D. Gegiou, and E. Fischer: An Example of a Reversible Photocyclization. Chem. Comm. 1965, 447.Google Scholar
  55. 53.
    -, and E. Fischer: Structure, Spectra, Photochemistry and Thermal Reactions of the 4a, 4b-Dihydrophenanthrenes. Accepted for publication. (J. chem. Soc. [London]).Google Scholar
  56. 54.
    Saltiel, J., E. D. Megarity, and K. G. Kneipp: The Mechanism of Direct cis-trans Photoisomerization of Stilbenes. J. Amer. chem. Soc. 88, 2336 (1966).CrossRefGoogle Scholar
  57. 55.
    Schulte-Frohlinde, D.: Über die thermische und katalytische cis-trans-Umlagerung substituierter Azobenzole. Ann. Chem. 612, 138 (1958).Google Scholar
  58. 56a.
    Schönberg, A., u. K. Junghans: Photosensibilisierte Dehydrierung des Bixanthylens und die Konstitution seiner thermochromen Form. Chem. Ber. 98, 2539 (1965).Google Scholar
  59. 56b.
    Schulte-Frohlinde, D., H. Blume, and H. Güsten: Photochemical cistrans Isomerization of Substituted Stilbenes. J. phys. Chem. 66, 2486 (1962).Google Scholar
  60. 57.
    Staab, H. A.: Einführung in die theoretische Organische Chemie, 3. Aufl., S. 398–399. Weinheim 1962.Google Scholar
  61. 58.
    Siehe No. 57, S. 341.Google Scholar
  62. 59.
    Wettermark, G., M. E. Langmuir, and D. G. Anderson: Catalysis of the cis → trans Isomerization of 2-Hydroxy-5-Methylazobenzene. J. Amer. chem. Soc. 87, 476 (1965).CrossRefGoogle Scholar
  63. 60.
    Wyman, G. M.: The Cis-Trans Isomerization of Conjugated Compounds. Chem. Revs. 55, 625 (1955).CrossRefGoogle Scholar
  64. 61.
    Zimmerman, G., L. Chow, and U. Paik: The Photochemical Isomerization of Azobenzene. J. Amer. chem. Soc. 80, 3528 (1958).CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 1967

Authors and Affiliations

  • Ernst Fischer
    • 1
  1. 1.Photochemical LaboratoryThe Weizmann Institute of ScienceRehovothIsrael

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