A new class of photochromic 1,2-diarylethenes; synthesis and switching properties of bis(3-thienyl)cyclopentenes

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Linda N. Lucas, Jan van Esch, Richard M. Kellogg and Ben L. Feringa


Abstract

A novel synthetic route to diarylethenes fixed in a cyclopentene based on titanium-mediated carbonyl coupling leads to bis(3-thienyl)cyclopentenes that show photochromic behaviour similar to that of known diarylethenes.


References

  1. M. Irie and K. Uchida, Bull. Chem. Soc. Jpn., 1998, 71, 985 CAS.
  2. P. Ball and L. Garwin, Nature, 1992, 355, 761 CrossRef; D. M. Eigler, C. P. Lutz and W. E. Rudge, Nature, 1991, 352, 600 CrossRef CAS; P. Ball, Designing the Molecular World, Chemistry at the Frontier, Princeton University Press, Princeton, NJ, 1994, p. 7 Search PubMed.
  3. G. M. Tsivgoulis and J.-M. Lehn, Chem. Eur. J., 1996, 2, 1399 CrossRef CAS.
  4. B. L. Feringa, W. F. de Jager and B. de Lange, Tetrahedron, 1993, 49, 8267 CrossRef CAS.
  5. M. Irie and M. Mohri, J. Org. Chem., 1988, 53, 803 CrossRef CAS.
  6. T. Yamaguchi, K. Uchida and M. Irie, J. Am. Chem. Soc., 1997, 119, 6066 CrossRef CAS.
  7. M. Hanazawa, R. Sumiya, Y. Horikawa and M. Irie, J. Chem. Soc., Chem. Commun., 1992, 206 RSC.
  8. H. Taniguchi, A. Shinpo, T. Okazaki, F. Matsui and M. Irie, Nippon Kagaku Kaishi, 1990, 1138.
  9. K. Uchida, Y. Kido, T. Yamaguchi and M. Irie, Bull. Chem. Soc. Jpn., 1998, 71, 1101 CAS.
  10. S. L. Gilat, S. H. Kawai and J.-M. Lehn, Chem. Eur. J., 1995, 1, 275 CrossRef CAS.
  11. A. Fürstner, A. Hupperts, A. Ptock and E. Janssen, J. Org. Chem., 1994, 59, 5215 CrossRef.
  12. C. Denekamp and B. L. Feringa, J. Chem. Soc., Perk. Trans. 1, in the press Search PubMed; C. Denekamp and B. L. Feringa, Adv. Mater., in the press Search PubMed.
  13. R. B. Woodward and R. Hoffmann, The Conservation of Orbital Symmetry, Verlag Chemie, New York, 1970 Search PubMed.
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