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.
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References
Lehn, J.M., Supramolecular Chemistry, Concepts and Perspectives, Weinheim: VCH, 1995.
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.
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.
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.
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.
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.
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.
Tseng, H.-R., Wu, D., Fang, N.X., Zhang, X., and Stoddart, J.F., Chem. Phys. Chem., 2004, vol. 5, p. 111.
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.
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.
Bissel, R.A., Crdova, E., Kaifer, A.E., and Stoddart, J.F., Nature, 1994, vol. 369, p. 133.
Raehm, L. and Sauvage, J.-P., Structure and Bonding, 2001, vol. 99, p. 55.
Gavina, P. and Sauvage, J.-P., Tetrahedron Lett., 1997, vol. 38, p. 3521.
Collin, J.-P., Gavina, P., and Sauvage, J.-P., Chem. Commun., 1996, p. 2005.
Collin, J.-P., Gavina, P., and Sauvage, J.-P., New J. Chem., 1997, vol. 21, p. 525.
Dietrich-Buchecker, C. and Sauvage, J.-P., Tetrahedron, 1990, vol. 46, p. 503.
Livoreil, A., Dietrich-Buchecker, C., and Sauvage, J.-P., J. Am. Chem. Soc., 1994, vol. 116, p. 9399.
Livoreil, A., Sauvage, J.-P., Armaroli, N., Balzani, V., Flamigni, L., and Venturi, B., J. Am. Chem. Soc., 1997, vol. 119, p. 12114.
Cardenas, D.J., Livoreil, A., and Sauvage, J.-P., J. Am. Chem. Soc., 1996, vol. 118, p. 11980.
Balzani, V., Credi, A., Raymo, F.M., and Stoddart, F.S., Angew. Chem., Int. Ed, 2000, vol. 39, p. 3348.
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.
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.
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.
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.
Venturi, M., Dumas, S., Balzani, V., Cao, J., and Stoddart, J.F., New J. Chem., 2004, vol. 28, p. 1032.
Liu, Y., Flood, A.H., and Stoddart, J.F., J. Am. Chem. Soc., 2004, vol. 126, p. 9150.
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.
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.
Nygaard, S., Laursen, B.W., Flood, A.H., Hansen, C.N., Jeppesen, J.O., and Stoddart, J.F., Chem. Commun., 2006, p. 144.
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.
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.
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.
Korybut-Daszkiewicz, B., Wieckowska, A., Bilewicz, R., Domagata, S., and Wozniak, K., Angew. Chem., Int. Ed. Engl., 2004, vol. 43, p. 1668.
Kaifer, A.E. and Gomez-Kaifer, M., Supramolecular Electrochemistry, Wiley-VCH, 1999.
Boulas, P.L., Gomez-Kaifer, M., and Echegoyen, L., Angew. Chem., Int. Ed, 1998, vol. 37, p. 216.
Niemz, A. and Rotello, V.M., Acc. Chem. Res., 1999, vol. 32, p. 44.
Kaifer, A.E., Acc. Chem. Res., 1999, vol. 32, p. 62.
Beer, P.D., Gale, P.A., and Chen, G.Z., J. Chem. Soc., Dalton Trans., 1999, p. 1897.
Matsue, T., Kato, T., Akiba, U., and Osa, T., Chem. Lett., 1985, vol. 14, p. 1825.
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.
Kim, H.-J., Jeon, W.S., Ko, Yo.H., and Kim, K., Proc. Natl. Acad. Sci. USA, 2002, vol. 99, p. 5007.
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.
Pina, F. and Parola, A.J., Coord. Chem. Rev., 1999, vol. 185–186, p. 149.
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.
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. ].
Beer, P.D. and Gale, P.A., Angew. Chem., Int. Ed, 2001, vol. 40, p. 487.
Lloris, J.M., Martinez-Manez, R., Soto, J., and Pardo, T., J. Organomet. Chem., 2001, vol. 637–639, p. 151.
Yoon, J., Kim, S.K., Singh, N.J., and Kim, K.S., Chem. Soc. Rev., 2006, vol. 35, p. 355.
Alvares, J., Wang, Y., Gomes-Kaifer, M., and Kaifer, A.E., Chem. Commun., 1998, p. 1455.
Wang, Y., Alvarez, J., and Kaifer, A.E., Chem. Commun., 1998, p. 1457.
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.
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.
Iki, N., Fujimoto, T., and Miyano, S., Chem. Lett., 1998, vol. 27, p. 625.
Ferguson, J., Hawkins, C.J., Kane-Maguire, L.A.P., and Lip, H., Inorg. Chem., 1969, vol. 8, p. 771.
Prshibil, R., Kompleksony v khimicheskom analize (Complexons in Chemical Analysis), Moscow: Inostrannaya Literatura, 1960.
Liu, Y. and Zhang, H.-Y., Thermochim. Acta, 2004, vol. 414, p. 65.
Iki, N., Horiuchi, T., Oka, H., Koyama, K., Morohashi, N., Kabuto, C., and Miano, S., J. Chem. Soc., Perkin Trans., 2001, p. 2219.
Amirov, R., McMillan, Z., Mustafina, A., Chukurova, I., Solovieva, S., Antipin, I., and Konovalov, A., Inorg. Chem. Commun, 2005, p. 821.
Scharff, J.-P. and Mahjoubi, M., New J. Chem., 1991, vol. 15, p. 883.
Matsumiya, H., Terazono, Y., Iki, N., and Miyano, S., J. Chem. Soc., Perkin Trans., 2002.
Galyus, Z., in Teoreticheskie osnovy elektrokhimicheskogo analiza (Theoretical Principles of Electrochemical Analysis), Moscow: Mir, 1974.
Spravochnik po elektrokhimii (Handbook of Electrochemistry) Sukhotin, A.M., Ed., Leningrad: Khimiya, 1981.
Gupta, N. and Linschitz, H., J. Am. Chem. Soc., 1997, vol. 119, p. 6384.
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.
Peaver, M.E. and Davis, J.D., J. Electroanal. Chem., 1963, vol. 6, p. 46.
Saveant, J.-M., J. Phys. Chem., 2001, vol. 105, p. 8995.
Matsue, T., Evans, D.H., Osa, T., and Kobayashi, N., J. Am. Chem. Soc., 1985, vol. 107, p. 3411.
Isnin, R., Salam, C., and Kaifer, A.E., J. Org. Chem., 1991, vol. 56, p. 35.
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.
Antropov, L.I., in Teoreticheskaya elektrokhimiya. Izd. 2-e, pererabot. i dop (Theoretical Electrochemistry, 2nd edition, revised and added), Moscow: Vysshaya shk., 1969.
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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.
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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
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DOI: https://doi.org/10.1134/S102319350907012X