Photoswitching of Intramolecular Magnetic Interaction Using Photochromic Compounds

  • Kenji Matsuda
  • Masahiro Irie
Part of the Springer Series in Chemical Physics book series (CHEMICAL, volume 70)

Summary

Recent advances in organic material chemistry have helped to realize several novel organic functional materials, including organic conductors, magnets, and nonlinear optical materials. One of the current frontiers in this field is molecular electronics, where a single molecule plays the role of one component in an electric circuit. For the realization of this goal, highly integrated materials with multiple functions are necessary. Photochromism is the light-induced reversible transformation of chemical species between two isomers that have different absorption spectra. The two isomers differ from each other not only in the absorption spectra but also in various physical and chemical properties. These property changes can, in principle, be utilized to control the function of organic materials. Two organic radicals placed at the two edges of a π-conjugative molecule interact magnetically through the framework via the exchange interaction J. Therefore photocontrol of the magnetism of the system is possible when the photochromic moiety is used as a backbone. In this chapter we will describe studies of the photoswitching of the intramolecular magnetism by incorporating two radical moieties into a photochromic diarylethene spin coupler. Photoswitching using a diarylethene dimer, which showed similar electric-circuit behavior, will also be discussed.

Keywords

Exchange Interaction Hyperfine Coupling Constant Switching Unit Ethyl Acetate Solution Photochromic Compound 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    C. Joachim, J.K. Gimzewski, A. Aviram: Nature 408, 541 (2000)CrossRefGoogle Scholar
  2. 2.
    V. Balzani, A. Credi, F.M. Raymo, J.F. Stoddart: Angew. Chem., Int. Ed. Engl. 39, 3349 (2000)Google Scholar
  3. 3.
    J.-M. Lehn: Supramolecular Chemistry: Concepts and Perspectives (VCH, Weinheim, 1995 )Google Scholar
  4. 4.
    M. Irie (ed.): Photochromism: Memories and Switches, Chem. Rev. 100, whole of issue 5 (2000)Google Scholar
  5. 5.
    G.H. Brown: Photochromism ( Wiley Interscience, New York, 1971 )Google Scholar
  6. 6.
    H. Dürr, H. Bouas-Laurent: Photochromism: Molecules and Systems ( Elsevier, Amsterdam, 1990 )Google Scholar
  7. 7.
    M. Blank, L.M. Soo, N.H. Wasserman, B.F. Erlanger: Science 214, 70 (1981)CrossRefGoogle Scholar
  8. 8.
    M. Irie, Y. Hirano, S. Hashimoto, K. Hayashi: Macromolecules 14, 262 (1981)CrossRefGoogle Scholar
  9. 9.
    S. Shinkai: Pure Appl. Chem. 59, 425 (1987)CrossRefGoogle Scholar
  10. 10.
    K. Ichimura, Y. Suzuki, T. Seki, A. Hosoki, K. Aoki: Langmuir 4, 1214 (1988)CrossRefGoogle Scholar
  11. 11.
    M. Irie: Adv. Polym. Sci. 94, 27 (1990)CrossRefGoogle Scholar
  12. 12.
    M. Irie: Adv. Polym. Sci. 110, 49 (1993)CrossRefGoogle Scholar
  13. 13.
    T. Ikeda, T. Sasaki, K. Ichimura: Nature 361, 428 (1993)CrossRefGoogle Scholar
  14. 14.
    M. Irie, M. Kato: J. Am. Chem. Soc. 107, 1024 (1985)CrossRefGoogle Scholar
  15. 15.
    Y. Atassi, J.A. Delaire, K. Nakatani: J. Phys. Chem. 99, 16320 (1995)CrossRefGoogle Scholar
  16. 16.
    M. Irie: Chem. Rev. 100, 1685 (2000)CrossRefGoogle Scholar
  17. 17.
    M. Irie, K. Uchida: Bull. Chem. Soc. Jpn. 71, 985 (1998)CrossRefGoogle Scholar
  18. 18.
    S.L. Gilat, S.H. Kawai, J.-M. Lehn: J. Chem. Soc., Chem. Commun. 1439 (1993)Google Scholar
  19. 19.
    S.L. Gilat, S.H. Kawai, J.-M. Lehn: Chem. Eur. J. 1, 275 (1995)CrossRefGoogle Scholar
  20. 20.
    M. Takeshita, M. Irie: J. Org. Chem. 63, 6643 (1998)CrossRefGoogle Scholar
  21. 21.
    T. Kawai, T. Kunitake, M. Irie: Chem. Lett. 905 (1999)Google Scholar
  22. 22.
    O. Kahn: Molecular Magnetism ( VCH, New York, 1993 )Google Scholar
  23. 23.
    A.A. Ovchinnikov: Theor. Chim. Acta 47, 297 (1978)CrossRefGoogle Scholar
  24. 24.
    H. Iwamura, N. Koga: Acc. Chem. Res. 26, 346 (1993)CrossRefGoogle Scholar
  25. 25.
    A. Rajca, J. Wongsriratanakul, S. Rajca: Science 294, 1503 (2001)CrossRefGoogle Scholar
  26. 26.
    T. Matsumoto, T. Ishida, N. Koga, H. Iwamura: J. Am. Chem. Soc. 114, 9952 (1992)CrossRefGoogle Scholar
  27. 27.
    S.J. Jacobs, D.A. Shultz, R. Jain, J. Novak, D.A. Dougherty: J. Am. Chem. Soc. 115, 1744 (1993)CrossRefGoogle Scholar
  28. 28.
    K. Matsuda, T. Yamagata, T. Seta, H. Iwamura, K. Hori: J. Am. Chem. Soc. 119, 8058 (1997)CrossRefGoogle Scholar
  29. 29.
    N.L. Frank, R. Clérac, J.-P. Sutter, N. Daro, O. Kahn, C. Coulon, M.T. Green, S. Golhen, L. Ouahab: J. Am. Chem. Soc. 122, 2053 (2000).CrossRefGoogle Scholar
  30. 30.
    W.T. Borden, E.R. Davidson: J. Am. Chem. Soc. 99, 4587 (1977)CrossRefGoogle Scholar
  31. 31.
    K. Matsuda, H. Iwamura: J. Am. Chem. Soc. 119, 7412 (1997)CrossRefGoogle Scholar
  32. 32.
    K. Matsuda, M. Irie: J. Am. Chem. Soc. 122, 7195 (2000)CrossRefGoogle Scholar
  33. 33.
    K. Matsuda, M. Irie: Chem. Lett. 16 (2000)Google Scholar
  34. 34.
    K. Matsuda, M. Irie: Tetrahedron Lett. 41, 2577 (2000)CrossRefGoogle Scholar
  35. 35.
    B. Bleany, K.D. Bowers: Proc. R. Soc. London A 214, 451 (1952)CrossRefGoogle Scholar
  36. 36.
    K. Matsuda, M. Irie: J. Am. Chem. Soc. 122, 8309 (2000)CrossRefGoogle Scholar
  37. 37.
    K. Matsuda, M. Irie: Chem. Eur. J. 7, 3466 (2001)CrossRefGoogle Scholar
  38. 38.
    R. Brière, R.-M. Dupeyre, H. Lemaire, C. Morat, A. Rassat, P. Rey: Bull. Soc. Chim. France 11, 3290 (1965)Google Scholar
  39. 39.
    S.H. Glarum, J.H. Marshall: J. Chem. Phys. 47, 1374 (1967)CrossRefGoogle Scholar
  40. 40.
    J.M. Tour: Acc. Chem. Res. 33, 791 (2000)CrossRefGoogle Scholar
  41. 41.
    J.M. Tour: Chem. Rev. 96, 537 (1996)CrossRefGoogle Scholar
  42. 42.
    T. Mitsumori, K. Inoue, N. Koga, H. Iwamura: J. Am. Chem. Soc. 117, 2467 (1995)CrossRefGoogle Scholar
  43. 43.
    K. Matsuda, M. Matsuo, M. Irie: Chem. Lett. 436 (2001)Google Scholar
  44. 44.
    K. Matsuda, M. Matsuo, M. Irie: J. Org. Chem. 66, 8799 (2001)CrossRefGoogle Scholar
  45. 45.
    K. Matsuda, M. Irie: J. Am. Chem. Soc. 123, 9896 (2001)CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2003

Authors and Affiliations

  • Kenji Matsuda
  • Masahiro Irie

There are no affiliations available

Personalised recommendations