Crown Compounds as Alkali and Alkaline Earth Metal Ion Selective Chromogenic Reagents

  • Makoto Takagi
  • Keihei Ueno


This article deals with the recent development of crown ethers which have added chromophoric functional groups within the molecule (crown ether dyes). These compounds are designed to bring about specific color changes on the interaction with such metal cations as alkali and alkaline earth metals, thus being able to serve as probes or photometric reagents selective for these metal ions. The chromophoric groups can bear a dissociable proton (or protons) or can be nonionic. In the former, the ion exchange between the proton and appropriate metal cations causes the color change, while in the latter, the coordination of the metal ion to the chromophoric donor or acceptor of the dye molecule induces a change of the charge transfer band of the dye. The proton-dissociable crown ether dyes are especially suited for extraction photometric determination of alkali and alkaline earth metal ions. Similarly, the neutral crown ether dyes are potentially useful for such determinations in lipophilic homogeneous media.


Alkaline Earth Metal Crown Ether Extraction Constant Glyceryl Ether Water Dioxane 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Sandell, E. B.: Colorimetric Determination of Traces of Metals, New York—London, Inter-science 1959Google Scholar
  2. 2.
    Cheng, K. L., Ueno, K., Imamura, T.: Handbook of Organic Analytical Reagents, Boca Raton, CRC Press 1982Google Scholar
  3. 3.
    Pedersen, C. J.: J. Am. Chem. Soc. 89, 7017 (1967)CrossRefGoogle Scholar
  4. 4.
    Takagi, M. et al.: Anal. Lett. 10, 1115 (1977)Google Scholar
  5. 5.
    Nakamura, H. et al.: Talanta 26, 921 (1979)CrossRefGoogle Scholar
  6. 6.
    Nakamura, H. et al.: Anal. Chem. 52, 1668 (1980)CrossRefGoogle Scholar
  7. 7.
    Lamb, J. D. et al.: in: Coordination Chemistry of Macrocyclic Compounds; Melson, G. A. (Ed.), p. 145, New York, Plenum Press 1979CrossRefGoogle Scholar
  8. 8.
    Dailey, N. K.: in: Synthetic Multidentate Macrocyclic Compounds, Izatt, R. M., Christensen, J. J. (Eds.), p. 207, New York, Academic Press 1978Google Scholar
  9. 9.
    Mallinson, P. R., Truter, M. R.: J. Chem. Soc., Perkin Trans. II 1818 (1972)Google Scholar
  10. 10.
    Ishizu, K. et al.: Chem. Lett. 227 (1978)Google Scholar
  11. 11.
    Pacey, G. E., Bubnis, B. P.: Anal. Lett. 13, 1085 (1980)CrossRefGoogle Scholar
  12. 12.
    Pacey, G. E. et al.: Analyst 106, 636 (1981)CrossRefGoogle Scholar
  13. 13.
    Yamashita, T. et al.: Bull. Chem. Soc. Jpn. 53, 1550 (1980)CrossRefGoogle Scholar
  14. 14.
    Nakamura, H. et al.: Chem. Lett. 1305 (1981)Google Scholar
  15. 15.
    Nishida, H. et al.: ibid. 1853 (1982)Google Scholar
  16. 16.
    Nakamura, H. et al.: Bunseki Kagaku 31, E131 (1982)CrossRefGoogle Scholar
  17. 17.
    Nakamura, H. et al.: Anal. Chim. Acta 139, 219 (1982)CrossRefGoogle Scholar
  18. 18.
    Takagi, M. et al.: unpublished workGoogle Scholar
  19. 19.
    Takagi, M. et al.: Anal. Chim. Acta 126, 185 (1981)CrossRefGoogle Scholar
  20. 20.
    Sumiyoshi, H. et al.: Talanta 24, 763 (1977)CrossRefGoogle Scholar
  21. 21.
    Kaneda, T. et al.: Tetrahedron Lett. 22, 4407 (1981)CrossRefGoogle Scholar
  22. 22.
    Nakashima, K. et al.: Chem. Lett. 1781 (1982)Google Scholar
  23. 23.
    Nakashima, K., Akiyama, S.: private communicationGoogle Scholar
  24. 24.
    Shinkai, S. et al.: J. Am. Chem. Soc. 104, 1967 (1982)CrossRefGoogle Scholar
  25. 25.
    Nishida, H. et al.: Mikrochim. Acta I, 281 (1981)Google Scholar
  26. 26.
    Shiga, M. et al.: Bunseki Kagaku, 32, E293 (1983)CrossRefGoogle Scholar
  27. 27.
    Takagi, M. et al.: Chem. Lett. 1179 (1978)Google Scholar
  28. 28.
    Tazaki, M. et al.: ibid. 571 (1982)Google Scholar
  29. 29.
    Uechi, T. et al.: Acta Crystallogr. B38, 433 (1982)CrossRefGoogle Scholar
  30. 30.
    Shinkai, S. et al.: J. Am. Chem. Soc. 104, 1960 (1982)CrossRefGoogle Scholar
  31. 31.
    Shinkai, S. et al.: Chem. Lett. 499 (1982)Google Scholar
  32. 32.
    Shinkai, S. et al.: Tetrahedron Lett. 20, 4569 (1979)CrossRefGoogle Scholar
  33. 33.
    Shiga, M. et al.: Chem. Lett. 1021 (1980)Google Scholar
  34. 34.
    Shinkai, S., Manabe, O.: J. Am. Chem. Soc. 105, 1851 (1983)CrossRefGoogle Scholar
  35. 35.
    Dix, J. P. Vögtle, F.: Angew. Chem. 90, 893 (1978);CrossRefGoogle Scholar
  36. Dix, J. P. Vögtle, F.: Angew. Chem. Int. Ed. Engl. 17, 857 (1978)Google Scholar
  37. 36.
    Dix, J. P., Vögtle, F.: Chem. Ber. 113, 457 (1980)CrossRefGoogle Scholar
  38. 37.
    Dix, J. P., Vögtle, F.: ibid. 114, 638 (1981)Google Scholar

Copyright information

© Springer-Verlag, Berlin, Heidelberg 1985

Authors and Affiliations

  • Makoto Takagi
    • 1
  • Keihei Ueno
    • 1
  1. 1.Department of Organic Synthesis, Faculty of EngineeringKyushu UniversityFukuoka 812Japan

Personalised recommendations