Bulletin of the Korean Chemical Society

  • 제33권8호
  • /
  • Pages.2683-2688
  • /
  • 2012
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

Facile Evaluation of Thermodynamic Parameters for Reverse Thermochromism of Indolinobenzospiropyran-6-carboxylates in Aqueous Binary Solvents

  • Keum, Sam-Rok (Department of Advanced Material Chemistry, Korea University, Sejong Campus) ;
  • Ma, So-Young (Department of Advanced Material Chemistry, Korea University, Sejong Campus) ;
  • Lim, Hyun-Woo (Department of Advanced Material Chemistry, Korea University, Sejong Campus) ;
  • Han, Tae-Hwi (Department of Advanced Material Chemistry, Korea University, Sejong Campus) ;
  • Choi, Kyu-Hyun (Department of Advanced Material Chemistry, Korea University, Sejong Campus)
  • 투고 : 2012.03.07
  • 심사 : 2012.05.16
  • 발행 : 2012.08.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

The position of the thermodynamic equilibrium for reverse thermochromic spiropyran 6-carboxylates (SP-COOHs) was easily determined in aqueous binary mixtures, such as water-methanol, water-acetonitrile and water-dimethyl sulfoxide. The existence of more than one type of interconvertible species of the ring-opened form of SP-COOH in aqueous binary solvents enables us to evaluate the molar extinction coefficients of the ring-opened species of SP-COOH and to obtain the thermodynamic parameters.

키워드

참고문헌

  1. Crano, J. C.; Guglielmetti, R. J. In Organic Photochromic and Thermochromic Compounds; Plenum Press: New York and London, 1999; p 11.
  2. Durr, H.; Bouas-Laurent, H. In Photochromism: Molecules and Systems; Amsterdam: Elsevier, 1990; Chapter 10, p 24.
  3. Kawata, S.; Kawata, Y. Chemical Reviews 2000, 100, 1777. https://doi.org/10.1021/cr980073p
  4. BerkovicValeri, G.; Weiss, K. V. Chemical Reviews 2000, 100, 1741. https://doi.org/10.1021/cr9800715
  5. Keum, S. R.; Ahn, S. M.; Lee, S. H. Dyes and Pigments 2004, 60, 55. https://doi.org/10.1016/S0143-7208(03)00138-4
  6. Keum, S. R.; Ku, B. S.; Shin, J. T.; Ko, J. J.; Buncel, E. Tetrahedron 2005, 61, 6720. https://doi.org/10.1016/j.tet.2005.05.005
  7. Maafi, M. Molecules 2008, 13, 2260. https://doi.org/10.3390/molecules13092260
  8. Suzuki, T.; Lin, F. T.; Priyadashy, S.; Weber, S. G. J. Chem. Soc. Chem. Comm. 1998, 24, 2685.
  9. Inouye, M.; Ueno, M.; Kitao, T. J. Am. Chem. Soc. 1990, 112, 8977. https://doi.org/10.1021/ja00180a051
  10. Wojtyk, J. T. C.; Kazmaier, P. M.; Buncel, E. Chem. Comm. 1998, 1703.
  11. Miyashita, A.; Iwamoto, A.; Kuwayama, T.; Shitara, H.; Aoki, Y.; Nihira, H. Chem. Lett. 1997, 965.
  12. Keum, S. R.; Roh, S. J.; Kim, S. E.; Lee, S. H.; Cho, C. H.; Kim, S. H.; Koh, K. N. Bull. Korean Chem. Soc. 2006, 27, 187. https://doi.org/10.5012/bkcs.2006.27.2.187
  13. Keum, S. R.; Noh, S. J.; Ahn, S. M.; Lim, S. S.; Kim, S. H.; Koh, K. Dyes and Pigments 2007, 74, 343. https://doi.org/10.1016/j.dyepig.2006.02.013
  14. Skwierczynski, R. D.; Connors, K. A. J. Chem. Soc. Perkin Trans. 2 1994, 467.
  15. Giusti, L. A.; Marini, V. G.; Machado, V. G. J. Mol. Liq. 2009, 150, 9. https://doi.org/10.1016/j.molliq.2009.09.002
  16. Keum, S. R.; Hur, M. S.; Kazmaier, P. M.; Buncel, E. Can. J. Chem. 1991, 69, 1940. https://doi.org/10.1139/v91-279
  17. Keum, S. R.; Lee, K. B.; Buncel, E. Tetrahedron Lett. 1994, 35, 1015. https://doi.org/10.1016/S0040-4039(00)79953-9
  18. Aldosin, S. In Organic Photochromic and Thermochromic Compounds, Vol 2; Crano, J. C., Gugelielmetti, R. J., Eds.; Kluwer: Dordrecht, 1999; p 297.
  19. Nishimura, N.; Miyake, J.; Sueishi, Y. Bull. Chem. Soc. Japn. 1989, 62, 1777. https://doi.org/10.1246/bcsj.62.1777
  20. Reichardt, C. In Solvents and Solvents Effects in Organic Chemistry; VCH Publishers: New York, NY, 1988; Chapter 4, p 107.
  21. Bertelson, R. C. In Photochromism; Brown, G. H., Ed.; Wiley- Intersciences: New York, 1971; Chapter 3, p 45.
  22. Samat, A.; Lokshin, V. In Photochromic and Thermochromic Compounds, Vol. 2; Crano, J. C., Guglielmetti, R. J., Eds., New York, 1999; Chapter 10, p 415.
  23. Wohl, C. J.; Kuciauskas, D. J. Phys. Chem. B 2005, 109, 21893. https://doi.org/10.1021/jp0538823
  24. Wojtyk, J. T. C.; Wasey, A.; Xiao, N. N.; Kazmaier, P. M.; Hoz, S.; Chen, Y. C.; Lemieux, R. P.; Buncel, E. J. Phys. Chem. A 2007, 111, 2511. https://doi.org/10.1021/jp068575r
  25. Kosower, E. M.; Hofmann, D.; Wallenfels, K. J. Am. Chem. Soc. 1962, 84, 2755 https://doi.org/10.1021/ja00873a023

피인용 문헌

  1. Symmetric Bis-Azospiropyrans: Synthesis, Characterization and Colorimetric Study vol.34, pp.6, 2013, https://doi.org/10.5012/bkcs.2013.34.6.1727
  2. Novel dimeric leuco-TAM dyes, 1,4-bis{(1E,3Z)-1,3-bis(1,3,3-trimethylindolin-2-ylidene)propan-2-yl}benzene derivatives: Structure and spectroscopic characterization vol.1014, pp.None, 2012, https://doi.org/10.1016/j.molstruc.2012.02.002
  3. Modeling colorimetric characteristics of ON-OFF behavior of photochromic dyes based on bis-azospiropyrans vol.1050, pp.None, 2013, https://doi.org/10.1016/j.molstruc.2013.07.040