Skip to main content
Log in

Electrochemistry of Calixarene and its Analytical Applications

  • Published:
Journal of inclusion phenomena and molecular recognition in chemistry Aims and scope Submit manuscript

Abstract

The electrochemistry of calixarene as a redox-dependent ionophore and its structural dependence are described. One or more redox-centers such as quinone, ferrocene, cobaltocenium and ruthenium bipyridine moieties have been introduced into the calixarene frame of the lower or upper rim. Although the electrochemical behavior depends mainly on the inherent redox property of these electrochemically active groups, the structural effect and solvent also play important roles, especially, in the presence of charged guests. When cationic species such as metal ions and ammonium ion are added to a quinone-functionalized calixarene solution, electron transfer to quinone is enhanced by the electrostatic effect or the formation of hydrogen bonds. In addition to redox-active hosts for voltammetric use, a number of calixarenes with novel structures have been developed as ionophores for potentiometric analysis and found to be successful for some target ions. In terms of Na+, Cs+ and Ca2+ selective ionophores for ion-selective electrodes, calixarenes are found to be excellent compared to crown ether derivatives or cryptands. Calixarenes can be also utilized to construct chemically modified electrodes, which are sensitive to gas species and biologically important compounds. The sophisticated design and synthesis of calixarenes are essential to specific potential applications to diverse fields.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. R. R. Lilienthal and D. K. Smith: Anal. Chem. 67, 3733 (1995).

    Google Scholar 

  2. A. Kaifer and L. Echegoyen: Redox Control of Cation Binding in Macrocyclic Systems in Y. Inoue and G. W. Gokel (Ed.), Cation Binding by Macrocycles, Marcel Dekker, New York, pp. 363–395, (1990).

    Google Scholar 

  3. P. D. Beer: Adv. Inorg. Chem. 39, 79 (1992).

    Google Scholar 

  4. W. H. Chan, K. K. Shiu, and X. H. Gu: Analyst 118, 863 (1993).

    Google Scholar 

  5. L. Zelikovich, J. Libman, and A. Shanzer: Nature 374, 790 (1995).

    Google Scholar 

  6. R. W. Wagner, J. S. Lindsey, J. Seth, V. Palaniappan, and D. F. Bocian: J. Am. Chem. Soc. 118, 3996 (1996).

    Google Scholar 

  7. E. Seward and F. Diederich: Tetrahedron Lett. 28, 5111 (1987).

    Google Scholar 

  8. C. D. Gutsche: Monographs in Supramolecular Chemistry, in J. F. Stoddard (Ed.), Calixarenes, Royal Society of Chemistry, Cambridge (1989).

    Google Scholar 

  9. S. R. Izatt, R. T. Hawkins, J. J. Christensen, and R. M. Izatt: J. Am. Chem. Soc. 107, 63 (1985).

    Google Scholar 

  10. M. A. McKervey and V. Böhmer: Chem. Britain August, 724 (1992).

  11. Y. Inoue, Y. Liu, L.-H. Tong, B.-J. Shen, and D.-S. Jin: J. Am. Chem. Soc. 115, 10637 (1993).

    Google Scholar 

  12. T. D. Chung: Ph.D. Thesis, Seoul National University (1997).

  13. D. Choi, T. D. Chung, S. K. Lee, S. K. Kang, T. Kim, S. K. Chang, and H. Kim: J. Electroanal. Chem. 387, 133 (1995).

    Google Scholar 

  14. L. Stryer: Biochemistry, 3rd Ed., Chapter 22, W. H. Freeman & Company, New York (1988).

    Google Scholar 

  15. W. A. Cramer and D. B. Knaff: in C. R. Cantor (Ed.), Energy Transduction in Biological Membrane, Chapter 5, Springer-Verlag, New York (1990).

    Google Scholar 

  16. K. Suga, M. Fujihira, Y. Morita, and T. Agawa: J. Chem. Soc., Faraday Trans. 87, 1575 (1991).

    Google Scholar 

  17. A. Casnati, E. Comeli, M. Fabbi, V. Bocci, G. Mori, F. Ugozzoli, A. M. Manotti-Lanfredi, A. Pochini, and R. Ungaro: Recl. Trav. Chim. Pays-Bas 112, 384 (1993).

    Google Scholar 

  18. M. Gómez-Kaifer, P. A. Reddy, C. D. Gutsche, and L. Echegoyen: J. Am. Chem. Soc. 116, 3580 (1994).

    Google Scholar 

  19. R. E. Wolf and S. R. Cooper: J. Am. Chem. Soc. 106, 4646 (1984).

    Google Scholar 

  20. P. D. Beer, Z. Chen, and P. A. Gale: Tetrahedron 50, 931 (1994).

    Google Scholar 

  21. P. D. Beer, Z. Chen, M. G. B. Drew, and P. A. Gale: J. Chem. Soc., Chem. Commun. 2207 (1994).

  22. P. D. Beer, Z. Chen, P. A. Gale, J. A. Heath, R. J. Knubley, and M. I. Odgen: J. Incl. Phenom. Mol. Recognit. Chem. 19, 343 (1994).

    Google Scholar 

  23. Z. Chen, P. A. Gale, J. A. Heath, and P. D. Beer: J. Chem. Soc. Faraday Trans. 90, 2931 (1994).

    Google Scholar 

  24. T. D. Chung, D. Choi, S. K. Lee, S. K. Kang, T. Kim, S. K. Chang, and H. Kim: J. Electroanal. Chem. 396, 431 (1995).

    Google Scholar 

  25. T. D. Chung, S. K. Kang, J. Kim, H-s. Kim, and H. Kim: J. Electroanal. Chem. 438, 71 (1997).

    Google Scholar 

  26. W. Oh, T. D. Chung, J. Kim, H. Kim, D. Hwang, K. Kim, and S.-K. Chang: Supramol. Chem. in press.

  27. P. D. Beer, A. D. Kneefe, and M. G. B. Drew: J. Organometal. Chem. 378, 437 (1989).

    Google Scholar 

  28. P. D. Beer, E. L. Tite, M. G. B. Drew, and A. Ibbotson: J. Chem. Soc., Dalton. Trans. 2543 (1990).

  29. P. D. Beer, A. D. Kneefe, V. Böhmer, H. Goldmann, W. Vogt, S. Lecocq, and M. Perrin: J. Organometal. Chem. 421, 265 (1991).

    Google Scholar 

  30. P. D. Beer, Z. Chen, M. G. B. Drew, and P. A. Gale: J. Chem. Soc., Chem. Commun. 1851 (1995).

  31. P. D. Beer, P. A. Gale, Z. Chen, and M. G. B. Drew: Supramol. Chem. 7, 241 (1996).

    Google Scholar 

  32. P. D. Beer, M. G. B. Drew, C. Hazlewood, D. Hesek, J. Hodacova, and S. E. Stokes: J. Chem. Soc., Chem. Commun. 229 (1993).

  33. P. D. Beer, D. Hesek, J. Kingston, D. K. Smith, S. E. Stokes, and M. G. B. Drew: Organometallics 14, 3288 (1995).

    Google Scholar 

  34. P. D. Beer, M. G. B. Drew, D. Hesek, and K. C. Nam: J. Chem. Soc., Chem. Commun. 107 (1997).

  35. P. D. Beer, Z. Chen, A. J. Goulden, A. Grieve, D. Hesek, F. Szemes, and T. Wear: J. Chem. Soc., Chem. Commun. 1269 (1994).

  36. F. Szemes, D. Hesek, Z. Chen, S. W. Dent, M. G. B. Drew, A. J. Goulden, A. R. Graydon, A. Grieve, R. J. Mortimer, T. Wear, J. S. Weightman, and P. D. Beer: Inorg. Chem. 35, 5868 (1996).

    Google Scholar 

  37. D. Bethell, G. Dougherty, and D. C. Cupertino: J. Chem. Soc., Chem. Commun. 675 (1995).

  38. H. C.-Y. Bettega, J.-C. Moutet, G. Ulrich, and R. Ziessel: J. Electroanal. Chem. 406, 247 (1996).

    Google Scholar 

  39. M. Gómez-Kaifer, P. A. Reddy, C. D. Gutsche, and L. Echegoyen: J. Am. Chem. Soc. 119, 5222 (1997).

    Google Scholar 

  40. T. D. Chung and H. Kim: unpublished data.

  41. L. Zhang, A. Macias, T. Lu, J. I. Gordon, G. W. Gokel, and A. Kaifer: J. Chem. Soc., Chem. Commun. 1017 (1993).

  42. L. Zhang, A. Macias, R. Isnin, T. Lu, G. W. Gokel, and A. Kaifer: J. Incl. Phenom. Mol. Recognit. Chem. 19, 361 (1994).

    Google Scholar 

  43. D. Diamond: Sensors and Analysis, in M. R. Smyth (Ed.), Electrochemistry, Elsevier, Amsterdam, p. 155, (1986).

    Google Scholar 

  44. K. M. O'Connor, D. W. M. Arrigan, and G. Svehla: Electroanalysis 7, 205 (1995).

    Google Scholar 

  45. M. Careri, A. Casnati, A. Guarinoni, A. Mangia, G. Mori, A. Pochini, and R. Ungaro: Anal. Chem. 65, 3156 (1993).

    Google Scholar 

  46. Y. Shibutani, H. Yoshinaga, K. Yakabe, and T. Shono: J. Incl. Phenom. Mol. Recognit. Chem. 19, 333 (1994).

    Google Scholar 

  47. H. Yamamoto and S. Shinkai: Chem. Lett. 1115 (1994).

  48. E. Bakker: Anal. Chem. 69 1061 (1997).

    Google Scholar 

  49. A. Cadogan, D. Diamond, S. Cremin, M. A. McKervey, and S. J. Harris: Anal. Proc. 28, 13 (1991).

    Google Scholar 

  50. A. Casnati, A. Pochini, R. Ungaro, C. Bocchi, F. Ugozzoli, R. J. M. Egberink, H. Struijk, R. Lutenberg, F. de Jong, and D. N. Reinhoudt: Chem. Eur. J. 2, 436 (1996).

    Google Scholar 

  51. Z.-L. Zhong, C.-P. Tang, C.-Y. Wu, and Y.-Y. Chan: J. Chem. Soc., Chem. Commun. 1737 (1995).

  52. T. D. Chung, J. Kim, J. Park, and H. Kim: manuscript to be submitted.

  53. J. A. J. Brunink, J. R. Haak, J. G. Bomer, D. N. Reinhoudt, M. A. McKervey, and S. J. Harris: Anal. Chim. Acta 254, 75 (1991).

    Google Scholar 

  54. J. A. J. Brunink, J. G. Bomer, J. F. J. Engbersen, W. Verboom, and D. N. Reinhoudt: Sens. Actuators B15-16, 195 (1993).

    Google Scholar 

  55. W. H. Chan, A.W.M. Lee, D.W. J. Kwong, W. L. Tam, and K. Wang: Analyst 121, 531 (1996).

    Google Scholar 

  56. K. Tóth, T. T. Lan, J. Jeney, M. Horvath, I. Bitter, A. Grün, B. Agai, and L. Töke: Talanta 41, 1041 (1994).

  57. A. Cadogan, Z. Gao, A. Lewenstam, A. Ivaska, and D. Diamond: Anal. Chem. 64, 2496 (1992).

    Google Scholar 

  58. Y. Tsujimura, M. Yokoyama, and K. Kimura: Anal. Chem. 67, 2401 (1995).

    Google Scholar 

  59. M. Telting-Diaz, D. Diamond, and M. R. Smyth: Anal. Chim. Acta 251, 149 (1991).

    Google Scholar 

  60. R. J. Forster, F. Regan, and D. Diamond: Anal. Chem. 63, 876 (1991).

    Google Scholar 

  61. R. J. Forster and D. Diamond: Anal. Chem. 64, 1721 (1992).

    Google Scholar 

  62. A. Cadogan, D. Diamond, M. R. Smyth, G. Svehla, M. A. McKervey, E. M. Seward, and S. J. Harris: Analyst 115, 1207 (1990).

    Google Scholar 

  63. C. Bocchi, M. Careri, A. Casnati, and G. Mori: Anal. Chem. 67, 4234 (1995).

    Google Scholar 

  64. Z. Asfari, C. Bressot, J. Vicens, C. Hill, J.-F. Dozol, H. Rouquette, S. Eymard, V. Lamare, and B. Tournois: Anal. Chem. 67, 3133 (1995).

    Google Scholar 

  65. M. Ogata, K. Fujimoto, and S. Shinkai: J. Am. Chem. Soc. 116, 4505 (1994).

    Google Scholar 

  66. K. M. O'Connor, G. Svehla, S. J. Harris, and M. A. McKervey: Talanta 39, 1549 (1992).

    Google Scholar 

  67. F. Arnaud-Neu, G. Barrett, D. Corry, S. Cremin, G. Ferguson, J. F. Gallagher, S. J. Harris, M. A. McKervey, and M. J. Schwing-Weill: J. Chem. Soc., Perkin Trans. 2 575 (1997).

  68. P. L. H. M. Cobben, R. J. M. Egberink, J. G. Bomer, P. Bergveld, W. Verboom, and D. N. Reinhoudt: J. Am. Chem. Soc. 114, 10573 (1992).

    Google Scholar 

  69. K. Odashima, K. Yagi, K. Tohda, and Y. Umezawa: Anal. Chem. 65, 1074 (1993).

    Google Scholar 

  70. W. H. Chan, K. K. Shiu, and X. H. Gu: Analyst 118, 863 (1993).

    Google Scholar 

  71. Z. Chen, P. A. Gale, and P. D. Beer: J. Electroanal. Chem. 393, 113 (1995).

    Google Scholar 

  72. M. J. Marsella, R. J. Newland, P. J. Carroll, and T. M. Swager: J. Am. Chem. Soc. 117, 9842 (1995).

    Google Scholar 

Download references

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chung, T.D. Electrochemistry of Calixarene and its Analytical Applications. Journal of Inclusion Phenomena 32, 179–193 (1998). https://doi.org/10.1023/A:1008059326436

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1008059326436

Navigation