Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Tailoring the Excited-State Intramolecular Proton Transfer (ESIPT) Fluorescence of 2-(2'-Hydroxyphenyl)benzoxazole Derivatives

  • Seo, Jang-Won (Organic Nano-Photonics Laboratory, School of Materials Science & Engineering, Seoul National University) ;
  • Kim, Se-Hoon (Organic Nano-Photonics Laboratory, School of Materials Science & Engineering, Seoul National University) ;
  • Park, Sang-Hyuk (Organic Nano-Photonics Laboratory, School of Materials Science & Engineering, Seoul National University) ;
  • Park, Soo-Young (Organic Nano-Photonics Laboratory, School of Materials Science & Engineering, Seoul National University)
  • Published : 2005.11.20
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Abstract

The excited-state intramolecular proton transfer (ESIPT) fluorescence in the 2-(2'-hydroxyphenyl)benzoxazole (HBO) derivatives with different electron donor and acceptor substituents was studied by spectroscopic and theoretical methods. Changes in the electronic transition, energy levels, and orbital diagrams of HBO analogues were investigated by the semi-empirical molecular orbital calculation and were correlated with the experimental spectral position of ESIPT keto emission. It was found that the presence of substituents, regardless of their nature, resulted in the red-shifted absorption relative to HBO. However, the spectral change of the ESIPT fluorescence was differently affected by the nature of substituent: hypsochromic shift with electron donor and bathochromic shift with electron acceptor.

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References

  1. Abou-Zied, O. K.; Jimenez, R.; Thompson, E. H. Z.; Millar, D. P.; Romesberg, F. E. J. Phys. Chem. A 2002, 106, 3665 https://doi.org/10.1021/jp013915o
  2. 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
  3. Kim, S.; Jang, D. W.; Park, S. Y.; Kim, K.; Jin, J.-I. Bull. Korean Chem. Soc. 2001, 22, 1407
  4. Kim, S.; Park, S. Y. Adv. Mater. 2003, 15, 1341 https://doi.org/10.1002/adma.200305050
  5. Tong, H.; Zhou, G.; Wang, L.; Jing, X.; Wang, F.; Zhang, J. Tetrahedron Lett. 2003, 44, 13107 https://doi.org/10.1016/S0040-4039(02)02504-2
  6. Acuna, A. U.; Costela, A.; Munoz, J. M. J. Phys. Chem. 1986, 90, 2807 https://doi.org/10.1021/j100404a005
  7. Keck, J.; Kramer, H. E. A.; Port, H.; Hirsch, T.; Fischer, P.; Rytz, G. J. Phys. Chem. 1996, 100, 14468 https://doi.org/10.1021/jp961081h
  8. Chou, P. T.; Martinez, M. L.; Clements, J. H. J. Phys. Chem. 1993, 97, 2618 https://doi.org/10.1021/j100113a024
  9. Klymchenko, A. S.; Demchenko, A. P. J. Am. Chem. Soc. 2002, 124, 12372 2618 https://doi.org/10.1021/ja027669l
  10. Hillebrand, S.; Segala, M.; Buckup, T.; Correia, R. R. B.; Horowitz, F.; Stefani, V. Chem. Phys. 2001, 273, 1 https://doi.org/10.1016/S0301-0104(01)00469-4
  11. Mordzinski, A.; Grabowska, A.; Kuhnle, W.; Krowszynski, A. Chem. Phys. Lett. 1983, 101, 291 https://doi.org/10.1016/0009-2614(83)87015-8
  12. Kauffman, J. M.; Bajwa, G. S. J. Heterocyclic. Chem. 1993, 30, 1613 https://doi.org/10.1002/jhet.5570300626
  13. Segala, M.; Domingues Jr., N. S.; Livotto, P. R.; Stefani, V. J. Chem. Soc., Perkin Trans. 1999, 2, 1123
  14. Doroshenko, A. O.; Posokhov, E. A.; Verezubova, A. A.; Ptyagina, L. M. J. Phys. Org. Chem. 2000, 13, 253 https://doi.org/10.1002/1099-1395(200005)13:5<253::AID-POC238>3.0.CO;2-D
  15. Doroshenko, A. O.; Posokhov, E. A.; Verezubova, A. A.; Ptyagina, L. M.; Skripkina, V. T.; Shershukov, V. M. Photochem. Photobiol. Sci. 2002, 1, 92 https://doi.org/10.1039/b107255m
  16. Rampey, M. E.; Halkyard, C. E.; Williams, A. R.; Angel, A. J.; Hurst, D. R.; Townsend, J. D.; Finefrock, A. E.; Beam, C. F.;Studer-Martinez, S. L. Photochem. Photobiol. 1999, 70(2), 176 https://doi.org/10.1111/j.1751-1097.1999.tb07987.x
  17. Ouyang, J.; Ouyang, C.; Fujii, Y.; Nakano, Y.; Shoda, T.; Nagano, T. J. Heterocyclic Chem. 2004, 41, 359 https://doi.org/10.1002/jhet.5570410309
  18. Kim, S.; Park, S. Y. Bull. Korean Chem. Soc. 1999, 20, 473
  19. Seo, J.; Kim, S.; Park, S. Y. J. Am. Chem. Soc. 2004, 126, 11154 https://doi.org/10.1021/ja047815i
  20. LeGourrierec, D.; Kharlanov, V. A.; Brown, R. G.; Rettig, W. J. Photochem. Photobiol. A: Chem., 2000, 130, 101 https://doi.org/10.1016/S1010-6030(99)00206-3
  21. Brewster, K.; Chittenden, R. A.; Harrison, J. M.; Inch, T. D.; Brown. C. J. Chem. Soc., Perkin Trans. 1 1976, 12, 1291
  22. Hamal, S.; Hirayama, F. J. Phys. Chem. 1983, 87, 83 https://doi.org/10.1021/j100224a020
  23. Klessinger, M.; Michl, J. Excited States and Photochemistry of Organic Molecules; VCH: New York, 1995
  24. Nagaoka, S.; Nakamura, A.; Nagashima, U. J. Photochem. Photobiol. A 2002, 54, 23

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