Skip to main content
Log in

Electrochemical properties of n-sulfonatothiacalyx[4]arene complexes with Fe3+ and [Co(dipy)3]3+ ions

  • Published:
Russian Journal of Electrochemistry Aims and scope Submit manuscript

Abstract

The electrochemical properties of n-sulfonatothiacalyx[4]arene (H4XNa4) complexes with [Co(dipy)3]3+ and Fe3+ ions were studied by means of cyclic voltammetry in aqueous solution at pH 2.5. The observed single-electron reduction of [Co(dipy)3]3+ bound extraspherically to the upper rim and Fe3+ ion bound intraspherically to the lower rim of n-sulfonatothiacalyx[4]arene in binary [Co(dipy)3]3+ · H3X5−, H3X5− · Fe3+, and ternary [Co(dipy)3]3+ · H3X5− · Fe3+ heterometal complexes was more difficult than in the free state. The reversible single-electron transfer to the metal ion results in lower binding energy ([Co(dipy)3]3+, ΔΔG 0 = 3.9 kJ/mol) or in full fast dissociation of the complex (Fe3+). The ternary complex in the solution forms the aggregates, in which inner encapsulated Fe(III) and Co(III) ions are not reduced on the electrode. Their quantitative reduction takes place by the relay mechanism of intra- and intermolecular electron transfer through electrochemically generated [Co(dipy)3]2+ outer ions.

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. Lehn, J.M., Supramolecular Chemistry, Concepts and Perspectives, Weinheim: VCH, 1995.

    Google Scholar 

  2. Anelli, P.L., Ashton, P.R., Ballardini, R., Balzani, V., Delgaro, M., Gandolfi, M.T., Goodnow, T.T., Kaifer, A.E., Philp, D., Pietraszkiewicz, M., Prodi, L., Reddington, M.V., Slawin, A.M.Z., Spencer, N., Stoddart, J.F., Vincent, C., and Williams, D.J., J. Am. Chem. Soc., 1992, vol. 114, p. 193.

    Article  CAS  Google Scholar 

  3. Ashton, P.R., Ballardini, R., Balzani, V., Credi, A., Gandolfi, M.T., Menzer, S., Perez-Garcia, L., Prodi, L., Stoddart, J.F., Venturi, M., White, A.J.P., and Williams, D.J., J. Am. Chem. Soc., 1995, vol. 117, p. 11171.

    Article  Google Scholar 

  4. Ballardini, R., Balzani, V., Credi, A., Braun, C.L., Gillard, R.E., Montalti, M., Philp, D., Soddart, J.F., Venturi, M., White, A.J.P., Williams, B.J., and Williams, D.J., J. Am. Chem. Soc., 1997, vol. 119, p. 12503.

    Article  CAS  Google Scholar 

  5. Ashton, P.R., Balzani, V., Credi, A., Kocian, O., Pasini, D., Prodi, L., Spencer, N., Stoddart, J.F., Tolley, M.S., Venturi, M., White, A.J.P., and Williams, D.J., Chem.-Eur. J., 1998, vol. 4, p. 590.

    Article  CAS  Google Scholar 

  6. Asakawa, M., Ashton, P.R., Balzani, V., Credi, A., Hamers, C., Mattersteig, G., Montalti, M., Shipway, A.N., Spencer, N., Stoddart, J.F., Tolley, M.S., Venturi, M., White, A.J.P., and Williams, D.J., Angew. Chem., 1998, vol. 110, p. 357.

    Article  Google Scholar 

  7. Flood, A.H., Peters, A.J., Vignon, S.A., Steuerman, D.W., Tseng, H.-R., Kang, S., Heath, J.R., and Stoddart, J.F., Chem.-Eur. J., 2004, vol. 10, p. 6558.

    Article  CAS  Google Scholar 

  8. Tseng, H.-R., Wu, D., Fang, N.X., Zhang, X., and Stoddart, J.F., Chem. Phys. Chem., 2004, vol. 5, p. 111.

    CAS  Google Scholar 

  9. Amabilino, D.B., Ashton, P.R., Balzani, V., Braun, C.L., Credi, A., Frecheu, J.M.J., Leon, J.W., Raymo, F.M., Spencer, N., Stoddart, J.F., and Venturi, M., J. Am. Chem. Soc., 1996, vol. 118, p. 12012.

    Article  CAS  Google Scholar 

  10. Amabilino, D.B., Asakawa, M., Ashton, P.R., Ballardini, R., Balzani, V., and Belohradsky, M., Credi, A., Higuchi, M., Raymo, F.M., Shimizu, T., Stoddart, J.F., Venturi, M., Yase, K., New J. Chem., 1998, vol. 22, p. 959.

    Article  CAS  Google Scholar 

  11. Bissel, R.A., Crdova, E., Kaifer, A.E., and Stoddart, J.F., Nature, 1994, vol. 369, p. 133.

    Article  Google Scholar 

  12. Raehm, L. and Sauvage, J.-P., Structure and Bonding, 2001, vol. 99, p. 55.

    Article  CAS  Google Scholar 

  13. Gavina, P. and Sauvage, J.-P., Tetrahedron Lett., 1997, vol. 38, p. 3521.

    Article  CAS  Google Scholar 

  14. Collin, J.-P., Gavina, P., and Sauvage, J.-P., Chem. Commun., 1996, p. 2005.

  15. Collin, J.-P., Gavina, P., and Sauvage, J.-P., New J. Chem., 1997, vol. 21, p. 525.

    CAS  Google Scholar 

  16. Dietrich-Buchecker, C. and Sauvage, J.-P., Tetrahedron, 1990, vol. 46, p. 503.

    Article  CAS  Google Scholar 

  17. Livoreil, A., Dietrich-Buchecker, C., and Sauvage, J.-P., J. Am. Chem. Soc., 1994, vol. 116, p. 9399.

    Article  CAS  Google Scholar 

  18. Livoreil, A., Sauvage, J.-P., Armaroli, N., Balzani, V., Flamigni, L., and Venturi, B., J. Am. Chem. Soc., 1997, vol. 119, p. 12114.

    Article  CAS  Google Scholar 

  19. Cardenas, D.J., Livoreil, A., and Sauvage, J.-P., J. Am. Chem. Soc., 1996, vol. 118, p. 11980.

    Article  CAS  Google Scholar 

  20. Balzani, V., Credi, A., Raymo, F.M., and Stoddart, F.S., Angew. Chem., Int. Ed, 2000, vol. 39, p. 3348.

    Article  CAS  Google Scholar 

  21. Balzani, V., Credi, A., Mattersteig, G., Matthews, O.A., Raymo, F.M., Stoddart, J.F., Venturi, M., White, A.J.P., and Williams, D.J., J.Org. Chem., 2000, vol. 65, p. 1924.

    Article  CAS  Google Scholar 

  22. Ballardini, R., Balzani, V., Clemente-Leon, M., Credi, A., Gandolfi, M.T., Ishow, E., Perkins, J., Stoddart, J.F., Tseng, H.-R., and Wenger, S., J. Am. Chem. Soc., 2002, vol. 124, p. 12786.

    Article  CAS  Google Scholar 

  23. Chen, Y., Jung, G.-Y., Ohlberg, D.A.A., Li, X., Stewart, D.R., Jeppesen, J.O., Nielsen, K.A., Stoddart, J.F., and Williams, R.S., Nanotecnology, 2003, vol. 14, p. 462.

    Article  CAS  Google Scholar 

  24. Bryce, M.R., Cooke, G., Duclairoir, F.M.A., John, P., Peperichka, D.F., Polwart, N., Rotello, V.M., Stoddart, J.F., and Tseng, H.-R., J. Mater. Chem., 2003, vol. 13, p. 2111.

    Article  CAS  Google Scholar 

  25. Venturi, M., Dumas, S., Balzani, V., Cao, J., and Stoddart, J.F., New J. Chem., 2004, vol. 28, p. 1032.

    Article  CAS  Google Scholar 

  26. Liu, Y., Flood, A.H., and Stoddart, J.F., J. Am. Chem. Soc., 2004, vol. 126, p. 9150.

    Article  CAS  Google Scholar 

  27. Huang, T.J., Tseng, H.-R., Sha, L., Lu, W., Brough, B., Flood, A.H., Yu, B.-D., Celestre, P.C., Chang, J.P., Stoddart, J.F., and Ho, C.-M., Nano Lett, 2004, vol. 4, p. 2065.

    Article  CAS  Google Scholar 

  28. Liu, Y., Flood, A.H., Bonvallet, P.A., Vignon, S.A., Northrop, B.H., Tseng, H.-R., Jeppesen, J.O., Huang, T.J., Brough, B., Baller, M., Magonov, S., Solares, S.D., Goddard, W.A., Ho, C.-M., and Stoddart, J.F., J. Am. Chem. Soc., 2005, vol. 127, p. 9745.

    Article  CAS  Google Scholar 

  29. Nygaard, S., Laursen, B.W., Flood, A.H., Hansen, C.N., Jeppesen, J.O., and Stoddart, J.F., Chem. Commun., 2006, p. 144.

  30. Beckman, R., Beverly, K., Boukai, A., Bunimovich, Y., Choi, J.W., DeIonno, E., Creen, J., Johnston-Halperin, E., Luo, Y., Sheriff, B., Stoddart, J.F., and Heath, J.R., Faraday Discuss, 2006, vol. 131, p. 9.

    Article  CAS  Google Scholar 

  31. Diaz, M.C., Illescas, B.M., Martin, N., Stoddart, J.F., Canales, M.A., Jimenez-Barbero, J., Sarova, G., and Guldi, D.M., Tetrahedron, 2006, vol. 62, p. 1998.

    Article  CAS  Google Scholar 

  32. Badjic, J.D., Ronconi, C.M., Stoddart, J.F., Balzani, V., Silvi, S., and Credi, A., J. Am. Chem. Soc., 2006, vol. 128, p. 1489.

    Article  CAS  Google Scholar 

  33. Korybut-Daszkiewicz, B., Wieckowska, A., Bilewicz, R., Domagata, S., and Wozniak, K., Angew. Chem., Int. Ed. Engl., 2004, vol. 43, p. 1668.

    Article  Google Scholar 

  34. Kaifer, A.E. and Gomez-Kaifer, M., Supramolecular Electrochemistry, Wiley-VCH, 1999.

  35. Boulas, P.L., Gomez-Kaifer, M., and Echegoyen, L., Angew. Chem., Int. Ed, 1998, vol. 37, p. 216.

    Article  CAS  Google Scholar 

  36. Niemz, A. and Rotello, V.M., Acc. Chem. Res., 1999, vol. 32, p. 44.

    Article  CAS  Google Scholar 

  37. Kaifer, A.E., Acc. Chem. Res., 1999, vol. 32, p. 62.

    Article  CAS  Google Scholar 

  38. Beer, P.D., Gale, P.A., and Chen, G.Z., J. Chem. Soc., Dalton Trans., 1999, p. 1897.

  39. Matsue, T., Kato, T., Akiba, U., and Osa, T., Chem. Lett., 1985, vol. 14, p. 1825.

    Article  Google Scholar 

  40. Kim, S.-Y., Jung, I.-S., Lee, E., Kim, J., Sakamoto, S., Yamaguchi, K., and Kim, K., Angew. Chem., Int. Ed. Engl., 2001, vol. 40, p. 2119.

    Article  CAS  Google Scholar 

  41. Kim, H.-J., Jeon, W.S., Ko, Yo.H., and Kim, K., Proc. Natl. Acad. Sci. USA, 2002, vol. 99, p. 5007.

    Article  CAS  Google Scholar 

  42. Rekharsky, M. and Inoue, Yo., Solvation effects in guest binding, in: Encyclopedia of Supramolecular Chemistry, Atwood, J.L. and Steed, J.W., Eds., New York: Marcel Dekker, 2004.

    Google Scholar 

  43. Pina, F. and Parola, A.J., Coord. Chem. Rev., 1999, vol. 185–186, p. 149.

    Article  Google Scholar 

  44. Le Derf, F., Mazari, M., Mercier, N., Levillain, E., Trippe, G., Riou, A., Richomme, P., Becher, J., Carin, J., Orduna, J., Gallego-Planas, N., Gorgues, A., and Salle, M., Chem.-Eur. J., 2001, vol. 7, p. 447.

    Article  Google Scholar 

  45. Yanilkin, V.V., Nastapova, N.V., Mamedov, V.A., Kalinin, A.A., and Gubskaya, V.P., Elektrokhimiya, 2007, vol. 43, p. 808 [Russ. J. Elektrochem. (Engl. Transl.), vol. 43, p. ].

    Google Scholar 

  46. Beer, P.D. and Gale, P.A., Angew. Chem., Int. Ed, 2001, vol. 40, p. 487.

    Article  Google Scholar 

  47. Lloris, J.M., Martinez-Manez, R., Soto, J., and Pardo, T., J. Organomet. Chem., 2001, vol. 637–639, p. 151.

    Article  Google Scholar 

  48. Yoon, J., Kim, S.K., Singh, N.J., and Kim, K.S., Chem. Soc. Rev., 2006, vol. 35, p. 355.

    Article  CAS  Google Scholar 

  49. Alvares, J., Wang, Y., Gomes-Kaifer, M., and Kaifer, A.E., Chem. Commun., 1998, p. 1455.

  50. Wang, Y., Alvarez, J., and Kaifer, A.E., Chem. Commun., 1998, p. 1457.

  51. Mustafina, A.R., Skripacheva, V.V., Gubskaya, V.P., Gryuner, M., Solov’eva, S.E., Antipin, I.S., Konovalov, A.I., and Khabikher, V.D., Izv. Akad. Nauk, Ser. Khim., 2004, p. 1453.

  52. Mustafina, A.R., Skripacheva, V.V., Gubaidullin, A.T., Latipov, Sh.K., Toropchina, A.V., Yanilkin, V.V., Solovieva, S.E., Antipin, I.S., and Konovalov, A.I., Inorg. Chem., 2005, vol. 44, p. 4017.

    Article  CAS  Google Scholar 

  53. Iki, N., Fujimoto, T., and Miyano, S., Chem. Lett., 1998, vol. 27, p. 625.

    Article  Google Scholar 

  54. Ferguson, J., Hawkins, C.J., Kane-Maguire, L.A.P., and Lip, H., Inorg. Chem., 1969, vol. 8, p. 771.

    Article  CAS  Google Scholar 

  55. Prshibil, R., Kompleksony v khimicheskom analize (Complexons in Chemical Analysis), Moscow: Inostrannaya Literatura, 1960.

    Google Scholar 

  56. Liu, Y. and Zhang, H.-Y., Thermochim. Acta, 2004, vol. 414, p. 65.

    Article  CAS  Google Scholar 

  57. Iki, N., Horiuchi, T., Oka, H., Koyama, K., Morohashi, N., Kabuto, C., and Miano, S., J. Chem. Soc., Perkin Trans., 2001, p. 2219.

  58. Amirov, R., McMillan, Z., Mustafina, A., Chukurova, I., Solovieva, S., Antipin, I., and Konovalov, A., Inorg. Chem. Commun, 2005, p. 821.

  59. Scharff, J.-P. and Mahjoubi, M., New J. Chem., 1991, vol. 15, p. 883.

    CAS  Google Scholar 

  60. Matsumiya, H., Terazono, Y., Iki, N., and Miyano, S., J. Chem. Soc., Perkin Trans., 2002.

  61. Galyus, Z., in Teoreticheskie osnovy elektrokhimicheskogo analiza (Theoretical Principles of Electrochemical Analysis), Moscow: Mir, 1974.

    Google Scholar 

  62. Spravochnik po elektrokhimii (Handbook of Electrochemistry) Sukhotin, A.M., Ed., Leningrad: Khimiya, 1981.

    Google Scholar 

  63. Gupta, N. and Linschitz, H., J. Am. Chem. Soc., 1997, vol. 119, p. 6384.

    Article  CAS  Google Scholar 

  64. Gomez, M., Gomes-Castro, C.Z., Padilla-Martinez, I.I., Martinez-Martinez, F.J., and Gonzalez, F.J., J. Electroanal. Chem., 2004, vol. 567, p. 269.

    Article  CAS  Google Scholar 

  65. Peaver, M.E. and Davis, J.D., J. Electroanal. Chem., 1963, vol. 6, p. 46.

    Article  Google Scholar 

  66. Saveant, J.-M., J. Phys. Chem., 2001, vol. 105, p. 8995.

    CAS  Google Scholar 

  67. Matsue, T., Evans, D.H., Osa, T., and Kobayashi, N., J. Am. Chem. Soc., 1985, vol. 107, p. 3411.

    Article  CAS  Google Scholar 

  68. Isnin, R., Salam, C., and Kaifer, A.E., J. Org. Chem., 1991, vol. 56, p. 35.

    Article  CAS  Google Scholar 

  69. Jeon, W.S., Moon, K., Park, S.H., Chun, H., Ko, Y.H., Lee, J.Y., Lee, E.S., Samal, S., Selvapalam, N., Rekharsky, M.V., Sindelar, V., Sobransingh, D., Inoue, Y., Kaifer, A.E., and Kim, K., J. Am. Chem. Soc., 2005, vol. 127, p. 12984.

    Article  CAS  Google Scholar 

  70. Antropov, L.I., in Teoreticheskaya elektrokhimiya. Izd. 2-e, pererabot. i dop (Theoretical Electrochemistry, 2nd edition, revised and added), Moscow: Vysshaya shk., 1969.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. V. Yanilkin.

Additional information

Original Russian Text © N.V. Nastapova, A.S. Stepanov, V.V. Yanilkin, V.A. Burilov, V.V. Skripacheva, A.R. Mustafina, S.E. Solov’eva, A.I. Konovalov, 2009, published in Elektrokhimiya, 2009, Vol. 45, No. 7, pp. 840–852.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nastapova, N.V., Stepanov, A.S., Yanilkin, V.V. et al. Electrochemical properties of n-sulfonatothiacalyx[4]arene complexes with Fe3+ and [Co(dipy)3]3+ ions. Russ J Electrochem 45, 783–794 (2009). https://doi.org/10.1134/S102319350907012X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S102319350907012X

Key words

Navigation