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Structural Chemistry

, Volume 16, Issue 2, pp 135–140 | Cite as

Synthesis, Structure and Photochromic Properties of 1-Phenyl-3-Methyl-4-(4-Bromobenzal)-Pyrazolone-5 Thiosemicarbazone

  • Guangfei Liu
  • Lang Liu
  • Dianzeng Jia
  • Kaibei Yu
Article

Abstract

A new organic photochromic compound containing pyrazolone-ring, 1-phenyl-3-methyl-4-(4-bromobenzal)-pyrazolone-5 thiosemicarbazone (PM4BrBP-TSC), was synthesized and characterized by elemental analyses and single crystal X-ray diffraction. The X-ray determination indicated that PM4BrBP-TSC is of orthorhombic system, space group Pbca with cell dimensions of a = 12.184(2) Å, b = 18.121(3) Å, c = 18.554(4) Å, V = 4096.4(12) Å3, Z = 8 and R = 0.0387. The photochromic properties and photocolored kinetics of PM4BrBP-TSC were studied by Time-dependent UV-Vis reflectance spectra and fluorescence spectra under 365 nm light irradiation. The crystal structure analysis showed that the photochromic properties were related to the photoisomerization from enol tautomer to keto one.

Keywords

Photochromic compound pyrazolone-ring crystal structure photoisomerization 

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References

  1. 1.
    Hoderbaun, M.; Dürr, H.; Hadjoudis, E. J. Photochem. Photobiol. A: Chem. 1991, 58, 37.Google Scholar
  2. 2.
    Ellam, R. M.; East, P. B.; Kelly, A.; Khan, R. M.; Lee, J. B.; Lindsey, D. C. Chem. Ind. 1974, 74.Google Scholar
  3. 3.
    Cohen, M. D.; Schmidt, G. M. J.; Flavian, S. J. Chem. Soc. 1964, 2041.Google Scholar
  4. 4.
    Cohen, M. D. Angew. Chem. 1975, 87, 439.Google Scholar
  5. 5.
    Cohen, M. D.; Schmidt, G. M. J. J. Chem. Phys. 1962, 66, 2442.Google Scholar
  6. 6.
    Dudek, G. D.; Dudek, E. P. J. Am. Chem. Soc. 1966, 88, 2407.Google Scholar
  7. 7.
    Higelin, D.; Sixl, H. Chem. Phys. 1983, 77, 391.Google Scholar
  8. 8.
    Barbara, P. F.; Rentzepis, P. M.; Brus, L. E. J. Am. Chem. Soc. 1980, 102, 2786.Google Scholar
  9. 9.
    Hadjoudis, E.; Vittorakis, M.; Moustakali-Mavridis, I. Tetrahedron 1987, 43, 1345.Google Scholar
  10. 10.
    Tang, X. C.; Jia, D. Z.; Liang, K.; Zhang, X. G.; Xia, X.; Zhou, Z. Y. J. Photochem. Photobiol. A: Chem. 2000, 134, 23.Google Scholar
  11. 11.
    Liu, L.; Jia, D. Z.; Ji, Y.L.; Yu, K. B. J. Photochem. Photobiol. A: Chem. 1903, 154, 117.Google Scholar
  12. 12.
    Jensen, B. S. Acta Chem. Scand. 1959, 13, 1668.Google Scholar
  13. 13.
    Frisch, M. J. GAUSSIAN 03, Gaussian, Inc., Pittsburgh, PA, 2003.Google Scholar
  14. 14.
    Kawato, T.; Koyama, H.; Kanatomi, H.; Isshiki, M. J. Photochem. 1985, 28, 103.Google Scholar
  15. 15.
    Casas, J. S.; Castiñeiras, A.; Lobana, T. S.; Sánchez, A.; Sordo, J.; García-Tasende, M. S. J. Chem. Crystallogr. 1901, 31, 329.Google Scholar

Copyright information

© Springer Science + Business Media, Inc. 2005

Authors and Affiliations

  • Guangfei Liu
    • 1
  • Lang Liu
    • 1
  • Dianzeng Jia
    • 1
  • Kaibei Yu
    • 2
  1. 1.Institute of Applied ChemistryXinjiang UniversityUrumqiPR China
  2. 2.Chengdu Institute of Organic ChemistryChinese Academy of SciencesChengduPR China

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