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Solvatokinetic and Solvatochromic Behavior of Bis(indolinobenzospiropyranyl) Sulfide Derivatives in Various Solvents

  • Keum, Sam-Rok (Department of New Material Chemistry, Korea University) ;
  • Ku, Byung-Soo (Department of New Material Chemistry, Korea University) ;
  • Kim, Sang-Eun (Department of New Material Chemistry, Korea University) ;
  • Choi, Yoon-Ki (Department of New Material Chemistry, Korea University) ;
  • Kim, Sung-Hoon (Department of Dyeing and Finishing, Kyungpook National University) ;
  • Koh, Kwang-Nak (Department of Pharmacy, Pusan National University)
  • Published : 2004.09.20

Abstract

Solvatokinetic and solvatochromic behavior of bis(indolinobenzospiropyranyl) sulfide derivatives 1a-1c have been studied in various solvents. The marked negative solvatochromism is exhibited for 1a and 1b in the whole region of solvent polarity examined. Whereas, it is found only in the polar solvent region ($E_T$ > 37) for 1c. The sensitivity order to the solvent media (slope values) is 1a > 1b > 1c. The branched linear plot with a zero slope was shown for the most sterically-hindered compound 1c in the less polar-solvent region (($E_T$ < 37). The biphasic plot is indicative of dual mechanistic process, i.e., a transition state with increased zwitter-ionic character in more polar solvents and electrocyclic process with an isopolar transition state in less polar solvents.

Keywords

References

  1. Photochromism; Brown, G. H., Ed.; Wiley Interscience: NewYork, 1971.
  2. Photochromism-Molecules and Systems, Studies in OrganicChemistry 40; Durr, H., Bouas-Laurent, H., Eds.; Elsevier:Amsterdam, 1990.
  3. Aramaki, S.; Atkinson, G. H. J. Am. Chem. Soc. 1992, 114, 438. https://doi.org/10.1021/ja00028a007
  4. Zhang, J. Z.; Schwartz, B. J.; King, J. C.; Harris, C. B. J. Am.Chem. Soc. 1992, 114, 1092. https://doi.org/10.1021/ja00029a051
  5. Keum, S. R.; Hur, M. S.; Kazmaier, P. M.; Buncel, E. Can. J.Chem. 1991, 69, 1940. https://doi.org/10.1139/v91-279
  6. Keum, S. R.; Lee, K. B.; Kazmaier, P. M.; Buncel, E. TetrahedronLett. 1994, 35(7), 1015. https://doi.org/10.1016/S0040-4039(00)79953-9
  7. Keum, S. R.; Lim, S. S.; Min, B. H.; Kazmaier, P. M.; Buncel, E.Dyes and Pigments 1996, 30(3), 225. https://doi.org/10.1016/0143-7208(95)00078-X
  8. Swansberg, S.; Choi, Y. K.; Keum, S. R.; Lee, M. J.; Buncel, E.;Lemieux, R. P. Liquid Crystals 1998, 24, 431.
  9. Keum, S. R.; Lee, M. J.; Shin, S. T. Liquid Crystals 2001, 28(11),1587. https://doi.org/10.1080/02678290110056878
  10. Keum, S. R.; Shin, J. T.; Lee, S. H.; Shin, S. T. Mol. Cryst. Liq.Crystal. 2004, 411, 119. https://doi.org/10.1080/15421400490434892
  11. Keum, S. R.; Ahn, S. M.; Lee, S. H. Dyes and Pigments 2004,60(1), 55. https://doi.org/10.1016/S0143-7208(03)00138-4
  12. Keum, S. R.; Lee, S. H.; Kang, S. O. Liquid Crystals 2004, inpress.
  13. Bertelson, R. C. J. Org. Chem. 1965, 30, 2875. https://doi.org/10.1021/jo01019a532
  14. Golodnyuk, T. I.; Vinogradova, V. I. Zh. Org. Khim. 1993, 29(9),1913.
  15. Keum, S. R.; Lee, K. B.; Kazmaier, P. M.; Manderville, R. A.;Buncel, E. Magn. Reson. Chem. 1994, 30, 1128. https://doi.org/10.1002/mrc.1260301119
  16. Keum, S.-R.; Lee, K. W. Bull. Korean Chem. Soc. 1992, 13(4),351. https://doi.org/10.1007/BF02705961
  17. Swansberg, S.; Buncel, E.; Lemieux, R. P. J. Am. Chem. Soc.2000, 122, 6594. https://doi.org/10.1021/ja0001613
  18. Buncel, E.; Rajagopal, S. Acc. Chem. Res. 1990, 23, 226. https://doi.org/10.1021/ar00175a004
  19. Botrel, A.; Lebeuze, A.; Jacques, P.; Straub, H. J. Chem. Soc.Faraday Trans. 2 1984, 80, 1235. https://doi.org/10.1039/f29848001235
  20. Wojtyk, J. T. C.; Wasey, A.; Kazmaier, P. M.; Hoz, S.; Buncel, E.J. Phys. Chem. A 2000, 104, 9046. https://doi.org/10.1021/jp001533x

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