Macromolecular Research

The Polymer Society of Korea (한국고분자학회)
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Photochromic Behavior and Its Stability of a New Bifunctional Dye Composed of Spirobenzopyran and a Cinnamoyl Moiety

  • Shen Kaihua (I State Key Laboratory of Fine Chemicals, Dalian University of Technology, Institute of Natural Sciences, Kyung Hee University) ;
  • Kim Jae Hong (Institute of Natural Sciences, Kyung Hee University) ;
  • Kim Go Woon (Department of Chemistry, Korea University) ;
  • Cho Min Ju (Department of Chemistry, Korea University) ;
  • Lee Sang Kyu (Department of Chemistry, Korea University) ;
  • Choi Dong Hoon (Department of Chemistry, Korea University)
  • Published : 2005.06.01
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Abstract

A novel bifunctional dye composed of spirobenzopyran and a cinnamoyl moiety was prepared and its photochromic behavior under the illumination of monochromatic UV light was investigated. This colorless bifunctional dye exhibits typical photochromism in both the film and in solution, through the structural and geometrical transformation from spirobenzopyran to merocyanine accompanied by a photocrosslinking reaction between the cinnamoyl moieties. Two kinds of photochemical reaction were selectively achieved by irradiation with monochromatic UV light at wavelengths of 275 and 365 nm, respectively. The effect of the selective photochemical reaction on the photochromism of the dye and its decaying behavior was investigated.

Keywords

References

  1. G. H. Brown, Ed., Techniques of Chemistry, Wiley-Interscience, New York, 1971, vol. III
  2. H. Durr and H. Bouas-Laurent, Ed., Photochromism Molecules and System, Elsiver, Amsterdam, 1990
  3. K. Matsuta and M. Irie, J. Am. Chem. Soc., 122, 7195 (2000) https://doi.org/10.1021/ja000605v
  4. K. Matsuta and M. lrie, Polyhedron, 20, 1391 (2001) https://doi.org/10.1016/S0277-5387(00)00624-0
  5. M. Irie, Chem. Rev., 100, 1685 (2000) https://doi.org/10.1021/cr980069d
  6. M. Morimoto, S. Kobatake, and M. Irie, Adv. Mater., 14, 1027 (2002) https://doi.org/10.1002/1521-4095(20020805)14:15<1027::AID-ADMA1027>3.0.CO;2-F
  7. N. Tamaoki, E. V Keuren, and H. Matsuda, Appl. Phys. Lett., 69, 1188 (1996) https://doi.org/10.1063/1.117107
  8. B. S. Cullum, J. Mobbley, J. S. Bogurd, M. Moscovitch, C. W. Phillips, and T. Vo-Pink, Anal. Chem., 72, 5612 (2000) https://doi.org/10.1021/ac000638t
  9. H. Tian and H.-Y. Tu, Adv. Mater., 12, 1597 (2000) https://doi.org/10.1002/1521-4095(200011)12:21<1597::AID-ADMA1597>3.0.CO;2-Q
  10. G. Berkoric, V. Krongauz, and V. Weiss, Chem. Rev., 100, 1741 (2000) https://doi.org/10.1021/cr9800715
  11. S. Hashimoto, A. Shimojima, T. Yuzawa, and H. Hiura, J. Mol. Struct., 1, 242 (1991)
  12. S. H. Kim, S. M. Lee, J. H. Park, J. H. Kim, and S. W. Kang, Dyes and Pigments, 45, 51 (2000) https://doi.org/10.1016/S0143-7208(00)00002-4
  13. S.-J. Sun, G., Schwarz, H. R. Kricheldorf, and T.-C. Chang, J. Polym. Sci.; Part A: Polym. Chem., 37, 1125 (1999) https://doi.org/10.1002/(SICI)1099-0518(19990415)37:8<1125::AID-POLA9>3.0.CO;2-J
  14. A. Rehab and N. Salahuddin, Polymer, 40, 2197 (1999) https://doi.org/10.1016/S0032-3861(98)00460-1
  15. N. Kawatzuki, T. Yamamoto, and H. Ono, Appl. Phys. Lett., 74, 935 (1999) https://doi.org/10.1063/1.123414
  16. Y.-K. Gong, F. Nakanishi, and K. Abe, Mol. Cryst. Liq. Cryst., 327, 123 (1999) https://doi.org/10.1080/10587259908026795
  17. D. H. Choi and Y. K. Cha, Bull. Kor. Chem. Soc., 23, 4 (2002)
  18. D. H. Choi, S. J. Oh, H. B. Cha, and J. Y. Lee, Euro. Polym. J., 37, 1951 (2001) https://doi.org/10.1016/S0014-3057(00)00100-2
  19. Y. Greenwald, G.. Cohen, J. Poplawaski, E. Ethrenfreund, S. Speiser, and D. Davidov, J. Am. Chem. Soc., 118, 1980 (1996)
  20. J. H. Lee, J. W. Park, J. M. Oh, and S. K. Choi, Macromolecules, 28, 377 (1995) https://doi.org/10.1021/ma00105a053
  21. H. R. Allcock and C. H. Kim, Macromolecules, 24, 2846 (1991) https://doi.org/10.1021/ma00010a032
  22. J. Biteau, F. Chaput, and J.-P. Boilot, J. Phys. Chem., 100, 9024 (1996) https://doi.org/10.1021/jp953607o