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Electrochemical Properties of Cationic Complexes of Molecular Containers from Cucurbituril Family

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Abstract

Electrochemical properties of cationic complexes of supramolecular cavitands from the cucurbit[n]uril (CBns) family are studied. Based on the analysis of a complex of systematic data on these compounds, basic regularities characterizing their adsorption behavior are formulated, in particular, the extremely high surface activity and unusually wide adsorption potential region over which the adsorption layer structure is transformed upon changes of the electrode charge value and sign. The varying of concentrations of reactants involved in the complex-formation reaction (the cavitand and inorganic cation) in the studied systems is shown to change significantly the observed picture of adsorption phenomena. The comparative analysis of adsorption data for systems containing supramolecular complexes of cucurbiturils with different cations can back qualitative estimating of their strength constants. It has been established by example of systems containing inclusive complexes of the СВ7 cavitand with organic cation (the cation of 3,3′-diethylthiocarbocyanine iodide dye) and with organic molecules (super-tough complexes with 1-hydroxyadamantan and ferrocene, the strength constants K of 109–1010 М–1 by order of magnitude), that including of neutral organic molecule into the cavitand cavity does not prevent the formation of an exclusive complex with sodium cation and that such a complex is not formed in the presence of organic cation in the cavitand cavity. It was demonstrated by example of the cobaltocene(Сос)/cobaltocenium(Сос+) redox-system studied in the solutions added with СВ7 and СВ7-free ones that the formation of adsorption layer of the Сос+ ⊂ СВ7 supramolecular complex particles preceding an electrode process leads to changing of the electrode reaction rate and mechanism.

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REFERENCES

  1. Behrend, R., Meyer, E., and Rusche, F., Über Condensationsproducte aus Glicoluril und Formaldehyd, Justus Liebigs Ann. Chem., 1905, Bd. 339, S. 1.

    Article  Google Scholar 

  2. Freeman, A., Mock, W.L., and Shih, N.Y., Cucurbituril, J. Am.Chem. Soc., 1981, vol. 103, no. 24, p. 7367.

    Article  CAS  Google Scholar 

  3. Masson, E., Ling, X., Joseph, R., Kyeremeh-Mensah, L., and Lu, X., Cucurbituril Chemistry: a tale of supramolecular success, RSC Advances, 2012, vol. 2, p. 1213.

    Article  CAS  Google Scholar 

  4. Khaleel, I., Assaf, Kh.I., and Nau, W.M., Cucurbiturils: from synthesis to high-affinity binding and catalysis, Chem. Soc. Rev., 2015, vol. 44, p. 394.

    Article  Google Scholar 

  5. Gerasko, O.A., Kovalenko, E.A., and Fedin, V.P., Macroscopic cavitands cucurbit[n]urils: perspectives of application in biochemistry, medicine and nanotechnologies, Russ. Chem. Rev., 2016, vol. 85, p. 795.

    Article  CAS  Google Scholar 

  6. Stenina, E.V. and Sviridova, L.N., Characteristics of the cucurbit[5]uril adsorption layer on the electrode/solution interface, Mendeleev Commun., 2015, vol. 25, p. 59.

    Article  CAS  Google Scholar 

  7. Stenina, E.V., Sviridova, L.N., and Ivanov, D.A., Adsorption of cucurbit[6]uril on the electrode/solution interface, Mendeleev Commun., 2016, vol. 26, p. 410.

    Article  CAS  Google Scholar 

  8. Stenina, E.V., Sviridova, L.N., and Petrov, N.Kh., Adsorption Phenomena in the Systems Containing Macrocyclic Cavitand Cucurbit [7]uryl, Russ. J. Electrochem., 2017, vol. 53, p. 103.

    Article  CAS  Google Scholar 

  9. Stenina, E.V., Sviridova, L.N., and Petrov, N.Kh., Properties of cucurbit[8]uril adsorption layer on the electrode/solution interface, Mendeleev Commun., 2018, vol. 28, p. 281.

    Article  CAS  Google Scholar 

  10. Stenina, E.V. and Sviridova, L.N., Adsorption phenomena in systems containing complexes of cucurbit[7]uril with organic compounds, J. Electroanal. Chem., 2019, vol. 833, p. 47.

    Article  CAS  Google Scholar 

  11. Frumkin, A.N. and Damaskin, B.B., Adsorption of organic compounds, in Modern Aspects of Electrochemistry, Bocris, J. and Conway, B., Eds., London: Butterworths, 1964, vol. 3, p. 149.

    Google Scholar 

  12. Lu, X. and Masson, A.E., Formation and Stabilization of Silver Nanoparticles with Cucurbit[n]urils (n = 5–8) and Cucurbituril-Based Pseudorotaxanes in Aqueous Medium, Langmuir, 2011, vol. 27, no. 6, p. 3051.

    Article  CAS  PubMed  Google Scholar 

  13. Moghaddam, S., Yang, Ch., Rekharsky, M., Ho Ko, Y., Inoue, Y., Kim, K., and Gilson, M.K., New Ultrahigh Affinity Host-Guest Complexes of Cucurbit[7]uril with Bicyclo[2.2.2]octane and Adamantane Guests: Thermodynamic Analysis and Evaluation of M2 Affinity Calculations, J. Am. Chem. Soc., 2011, vol. 133, p. 3570.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Lu, Cui, Suresh, Gadde, Wei, Li, and Kaifer, A.E., Electrochemistry of the Inclusion Complexes Formed Between the Cucurbit[7]uril Host and Several Cationic and Neutral Ferrocene Derivatives, Langmuir, 2009, vol. 25, p. 13763.

  15. Petrov, N.Kh., Ivanov, D.A., Golubkov, D.V., Gromov, S.P., and Alfimov, M.V., The effect of cucurbit[7]uril on photophysical properties of aqueous solution of 3,30-diethylthiacarbocyanine iodide dye, Chem. Phys. Lett., 2009, vol. 480, p. 96.

    Article  CAS  Google Scholar 

  16. Ong, W. and Kaifer, A.E., Unusual Electrochemical Properties of the Inclusion Complexes of Ferrocenium and Cobaltocenium with Cucurbit[7]uril, Organometallics, 2003, vol. 22, p. 4181.

    Article  CAS  Google Scholar 

  17. Freitag, M. and Gallopini, E., Cucurbituril Complexes of Viologens Bound to TiO2 Films, Langmuir, 2010, vol. 26, p. 8262.

    Article  CAS  PubMed  Google Scholar 

  18. Stenina, E.V., Sviridova, L.N., Krivenko, A.G., Kochergin, V.K., and Manzhos, R.A., Electrochemistry of the inclusion complexes of metallocene derivatives with cucurbit[7]uril on glassy carbon and mercury electrodes, J. Electroanal. Chem., 2021, vol. 901. https://doi.org/10.1016/j.jelechem.2021.115746

  19. Sobransingh, D. and Kaifer, A.E., New Dendrimers Containing a Single Cobaltocenium Unit Covalently Attached to the Apical Position of Newkome Dendrons:  Electrochemistry and Guest Binding Interactions with Cucurbit[7]uril, Langmuir, 2006, vol. 22, no. 25, p. 10540.

    Article  CAS  PubMed  Google Scholar 

  20. Laviron, E., Adsorption, autoinhibition and autocatalysis in polarography and in linear potential sweep voltammetry, J. Electroanal. Chem., 1974, vol. 52, p. 355.

    Article  CAS  Google Scholar 

  21. Damaskin, B.B., Safonov, V.A., and Baturina, O.A., Statistical Method of Determining Adsorption Parameters for Simple Organic Compounds from Nonequilibrium Differential Capacitance Curves, Russ. J. Electrochem., 1997, vol. 33, p. 105.

    CAS  Google Scholar 

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Funding

This work is supported by the Program of development of Moscow State University, NIR no. АААА-А21-121011590088-4.

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  1. M.V. Lomonosov Moscow State University, 119991, Moscow, Russia

    E. V. Stenina & L. N. Sviridova

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  1. E. V. Stenina
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  2. L. N. Sviridova
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Correspondence to E. V. Stenina or L. N. Sviridova.

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Translated by Yu. Pleskov

A tribute to outstanding electrochemist Oleg Aleksandrovich Petrii (1937–2021).

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Stenina, E.V., Sviridova, L.N. Electrochemical Properties of Cationic Complexes of Molecular Containers from Cucurbituril Family. Russ J Electrochem 58, 1020–1032 (2022). https://doi.org/10.1134/S1023193522110106

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