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Excited-state Intramolecular Proton Transfer of 1,5- and 1,8-Dihydroxyanthraquinones Chemically Adsorpted onto SiO2, SiO2-Al2O3, and Al2O3 Matrices

  • Cho, Dae-Won (Department of Chemistry, Chosun University) ;
  • Song, Ki-Dong (Department of Chemistry, Chosun University) ;
  • Park, Seong-Kyu (Department of Chemistry, Chosun University) ;
  • Jeon, Ki-Seok (Fusion Biotechnology Research Center, Korea Research Institute of Chemical Technology) ;
  • Yoon, Min-Joong (Department of Chemistry, Chungnam National University)
  • Published : 2007.04.20

Abstract

In order to investigate the excited-state intramolecular proton transfer (ESIPT) process of dihydroxyanthraquinones (DHAQ; 1,5-DHAQ and 1,8-DHAQ) in organic-inorganic hybrid matrices, transparent SiO2, SiO2- Al2O3, and Al2O3 matrices chemically bonded with DHAQ were prepared using a sol-gel technique. The absorption maxima of 1,5- and 1,8-DHAQ in SiO2 matrices are observed at around 420 nm, whereas those of DHAQ in both SiO2-Al2O3 and Al2O3 matrices are markedly shifted to longer wavelength compared with those in SiO2 matrix. This indicates that DAHQ forms a chemical bond with an Al atom of Al2O3. The DHAQ in SiO2 matrix shows a markedly Stokes-shifted emission which is originated from the ESIPT in DHAQ. Based on the emission lifetimes of DHAQ, the ESIPT of DHAQ was found to be strongly affected by the chemical interaction with Al atom in the Al2O3-related matrices.

Keywords

References

  1. Laine, R. M.; Sanchez, C.; Brinker, C. J.; Giannelis, E. Organic/Inorganic Hybrid Materials; Materials Research Society: Warrendale, PA, 1998; Vol. 519
  2. Kelin, L. C.; Francis, L. F.; De Duire, M. R.; Mark, J. E. Organic/Inorganic Hybrid Materials II; Materials Research Society: Warrendale, PA, 1999; Vol. 576
  3. Laine, R. M.; Sanchez, C.; Brinker, C. J.; Giannelis, E. Organic/ Inorganic Hybrid Materials-2000; Materials Research Society: Warrendale, PA, 2000; Vol. 628
  4. Sanchez, C.; Laine, R. M.; Yang, S.; Brinker, C. J. Organic/Inorganic Hybrid Materials- 2002; Materials Research Society: Warrendale, PA, 2002; Vol. 726
  5. Sanchez, C.; Schubert, U.; Laine, R. M.; Chujo, Y. Organic/ Inorganic Hybrid Materials-2004; Materials Research Society: Warrendale, PA, 2004; Vol. 847
  6. Avnir, D.; Kaufman, V. R.; Reisfeld, R. J. Non-Cryst. Solids 1985, 74, 395
  7. Zink, J. I.; Dunn, B. S. J. Ceram. Soc. Jpn. 1991, 99, 878 https://doi.org/10.2109/jcersj.99.878
  8. Reisfeld, R. Proc. SPIE 1990, 29, 1328
  9. Tani, T.; Namikawa, H.; Arai, K. J. Appl. Phys. 1985, 58, 3559 https://doi.org/10.1063/1.335731
  10. Seo, Y. S.; Lee, C.; Lee, K. H.; Yoon, K. B. Angew. Chem. Int. Ed. 2005, 44, 910 https://doi.org/10.1002/anie.200461972
  11. Zhang, J.; Yamashita, H.; Anpo, M. Chem. Lett. 1997, 1027
  12. Zhang, J.; Matsuoka, M.; Yamashita, H.; Anpo, M. Langmuir 1999, 15, 77 https://doi.org/10.1021/la980860h
  13. Ishiwaki, T.; Inoue, H.; Makishima, A. J. Non-Cryst. Solids 1996, 203, 43
  14. Chapul, F.; Boilol, J.-P.; Riehl, D.; Levy, Y. Sol-Gel Optics III 1994, 286
  15. Suratwala, T.; Gardlund, Z.; Boulton, J. M.; Uhlmann, D. R. Sol-Gel Opitcs III 1991, 310
  16. Keeling-Tucker, T.; Brennan, J. D. Chem. Mater. 2001, 13, 3331
  17. Remers, W. A. The Chemistry of Antitumor Antibiotics; John Wiley: New York, 1979; Vol. 1
  18. Asquith, R. S.; Ingham, P. J. Soc. Dyes Colour 1978, 94, 12
  19. Van Benthem, M. H.; Gillispie, G. D. J. Phys. Chem. 1984, 88, 2954 https://doi.org/10.1021/j150658a008
  20. Formoshinho, S. J.; Arnaut, L. G. J. Photochem. Photobiol. A:Chem. 1993, 75, 21 https://doi.org/10.1016/1010-6030(93)80158-6
  21. Choi, J. R.; Jeoung, S. C.; Cho, D. W. Bull. Korean Chem. Soc. 2003, 24, 1675 https://doi.org/10.5012/bkcs.2003.24.11.1675
  22. Choi, J. R.; Jeoung, S. C.; Cho, D. W. Chem. Phys. Lett. 2004, 385, 384 https://doi.org/10.1016/j.cplett.2004.01.011
  23. Cho, D. W.; Kim, S. H.; Yoon, M.; Jeoung, S. C. Chem. Phys. Lett. 2004, 391, 314 https://doi.org/10.1016/j.cplett.2004.05.013
  24. Cho, D. W.; Yoon, M. J. Photochem. Photobiol. A: Chem. 2006, 181, 414 https://doi.org/10.1016/j.jphotochem.2005.12.027
  25. Kim, Y. H.; Yoon, M.; Cho, D. W.; Jeoung, S. C.; Kim, D. Bull. Korean Chem. Soc. 1997, 18, 803
  26. Sauter, B.; Basché, T.; Brauchle, C. J. Opt. Soc. Am. 1992, B9, 804
  27. Basche, T.; Bräuchle, C. Chem. Phys. Lett. 1991, 181, 179 https://doi.org/10.1016/0009-2614(91)90352-A
  28. Flom, S. R.; Barbara, P. F. J. Phys. Chem. 1985, 89, 4489 https://doi.org/10.1021/j100267a017
  29. Tsipis, C. A.; Bakalbassis, E. G. Can. J. Chem. 1982, 60, 2477 https://doi.org/10.1139/v82-358

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