Photochromics for the Future

  • Harry G. Heller
Chapter

Abstract

A photochromic organic compound A is a compound that undergoes a major reversible color change on irradiation at an appropriate wavelength (λa) to form a more highly colored species B, which undergoes the reverse reaction either thermally or photochemically on irradiation at a second wavelength (λb):
$$ A\mathop{ \rightleftharpoons }\limits_{{{{\lambda }_{b}}orheat}}^{{{{\lambda }_{a}}}} B $$

Keywords

Quantum Efficiency Colored Form Succinic Anhydride High Quantum Efficiency Photochromic Property 
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.
This is a preview of subscription content, log in to check access.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    E. ter Meer, Über Dinitroverbindungen der Fettreihe, Annalen 181, 1–22 (1876).Google Scholar
  2. 2.
    Y. Hirshberg, Reversible formation and eradication of colors by irradiation at low temperatures. A photochemical memory model, J. Am. Chem. Soc. 78, 2304–2312 (1956).CrossRefGoogle Scholar
  3. 3.
    G. H. Brown, Photochromism, Techniques of Chemistry, Vol. 3, Wiley Interscience, New York (1971).Google Scholar
  4. 3.
    Y. Hirshberg, Reversible formation and eradication of colors by irradiation at low temperatures. A photochemical memory model, J. Am. Chem. Soc. 78, 2304–2312 (1956).CrossRefGoogle Scholar
  5. 4.
    H. G. Heller, S. N. Oliver, I. Tomlinson, and J. Whittall, Patent 0246 114 (1987).Google Scholar
  6. 5.
    R. B. Woodward and R. Hoffmann, Conservation of orbital symmetry. Ac. Chem. Res. 1, 17–22 (1968).CrossRefGoogle Scholar
  7. 6.
    E. N. Marvell, G. Caple, and B. Schatz, Thermal valence isomerizations. Stereochemistry of the 2,4,6-octatriene to 5,6-dimethyl-1,3-cyclohexadiene ring closure, Tetrahedron Lett. 385–389 (1965).Google Scholar
  8. 7.
    H. Stobbe, Die Fulgide, Annalen 380, 1–129 (1911).Google Scholar
  9. 8.
    R. J. Hart and H. G. Heller, Overcrowded molecules—Part 7: Thermal and photochemical reactions of photochromic (E)- and (Z)-benzylidene(diphenylmethylene)succinic anhydrides and imides. J. Chem. Soc. Perkin Trans. 1, 1487–1492 (1972).Google Scholar
  10. 9.
    H. G. Heller, P. J. Darcy, S. Patharakorn, R. D. Piggott, and J. Whittall, Photochromic systems-Part 1: Photochemical studies on (E)-2-isopropylidene-3-[l-(3,4,5-trimethoxyphenyl) ethylidene]succinic trihydride and related compounds, J. Chem. Soc. Perkin Trans. 1, 315–319 (1986).Google Scholar
  11. 10.
    H. G. Heller and R. M. Megit, Overcrowded molecules—Part 9: Fatigue-free photochromic systems involving (E)-2-isopropylidene-3-(mesitylmethylene)succinic anhydride and N-phenylimide, J. Chem. Soc. Perkin Trans. 1, 923–927 (1974). H. G. Heller and H. Gonzenbach, unpublished results.Google Scholar
  12. 11.
    H. G. Heller and J. R. Langan, Photochromic heterocyclic fulgides- Part 3: The use of (E)-α-(2,5dimethyl-3-furylethylidene (isopropylidene) succinic anhydride as a simple convenient chemical actinometer, J. Chem. Soc. Perkin Trans. II, 341 (1981).Google Scholar
  13. 12.
    M. Irie and M. Mohri, Thermally irreversible photochromic systems. Reversible photocyclization of diarylethene derivatives. J. Org. Chem. 53, 803–808 (1988).CrossRefGoogle Scholar
  14. 13.
    H. G. Heller, Organic fatigue-resistant photochromic imaging materials, TEE Proc. 150, 209–211 (1983).Google Scholar
  15. 14.
    H. G. Heller, S. A. Harris, W. Johncock, S. N. Oliver, P. J. Strydom, and J. Whittall, Photochromic heterocyclic fulgides. Part 4. The thermal and photochemical reactions of (E)-isopropylidene-[α-2and 3-(3-thienyl)ethylidene]succinic anhydrides and related compounds, J. Chem. Soc. Perkin Trans. 1, 957–961 (1985).Google Scholar
  16. 15.
    Y. Kurita, Y. Yokoyama, T. Goto, T. Inoue, and M. Yokoyama, Fulgides as efficient photochromic compounds. Role of the substituent on furylalkylidene moiety of furyl fulgides in the photoreaction. Chem. Lett.1049–1052 (1988).Google Scholar
  17. 16.
    H. G. Heller, New fatigue-resistant organic photochromic materials, The Royal Society of Chemistry Special Publication No. 60. Fine Chemicals for the Electronics Industry. pp. 120–135 (1986).Google Scholar
  18. 17.
    H. G. Heller, B. Helliwell, and D. Wood, unpublished results.Google Scholar
  19. 18.
    H. G. Heller, S. N. Oliver, J. Whittall, W. Johncock, P. J. Darcy, and C. Trundle, Photochromic compounds and their uses in photoreactive lenses, E.P.A. 0 140540 (1984).Google Scholar
  20. 19.
    T. Tanaka, S. Imura, and Y. Kida, Photochromic compounds, E.P.A. 0 316179 (1988).Google Scholar
  21. 20.
    R. S. Becker and J. Kolc, Proof of structure of the coloured photoproducts of chromenes and spiropyrans, J. Phys. Chem. 71, 4045–4047 (1967).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1991

Authors and Affiliations

  • Harry G. Heller
    • 1
  1. 1.School of Chemistry and Applied ChemistryUniversity of Wales College of CardiffCardiffUK

Personalised recommendations