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Chemistry of Heterocyclic Compounds

, Volume 46, Issue 9, pp 1076–1083 | Cite as

New organic ligands of the terpyridine series: modification of gold nanoparticles, preparation of coordination compounds with Cu(I), catalysis of oxidation reactions

  • A. G. Majouga
  • R. B. Romashkina
  • A. S. Kashaev
  • R. D. Rahimov
  • E. K. BeloglazkinaEmail author
  • N. V. Zyk
Article

Organic ligands containing terpyridine and disulfide groupings linked between one another by a bonding –O(CH2)n- (n = 6, 12) fragment have been synthesized. Gold nanoparticles of mean size 1.8 nm modified with the indicated ligand were obtained by the method of Brust. By methods of electron spectroscopy and cyclic voltamperometry, the possibility of forming of coordinated compounds on the surface of gold nanoparticles modified by a terpyridine ligand, on interaction with Cu(MeCN)4ClO4 has been shown. The obtained nanoparticles catalyze the oxidation of 2,4-di-tert-butylphenol into 3,3',5,5'-tetra(tert-butyl)biphenyl-2,2'-diol.

Keywords

disulfides complexes of metal peroxides copper(I) Au nanoparticles terpyridines catalysis electrochemistry 

References

  1. 1.
    I. A. Koval, P. Gamez, C. Belle, K. Semeczi, and J. Reedijkl, Chem. Soc. Rev., 35, 814 (2006).CrossRefGoogle Scholar
  2. 2.
    P. Gamez, P. G. Aubel, W. L. Driessen, and J. Reedijk, Chem. Soc. Rev., 30, 376 (2001).CrossRefGoogle Scholar
  3. 3.
    L. M. Mirica, X. Ottenwaelder, and D. Stack, Chem. Rev., 104, 1013 (2004).CrossRefGoogle Scholar
  4. 4.
    W. Brackman and E. Havinga, Rec. Trav. Chim., 74, 937 (1955).CrossRefGoogle Scholar
  5. 5.
    P. Capdevielle and M. Maumy, Tetrahedron. Lett., 23, 1573 (1982).CrossRefGoogle Scholar
  6. 6.
    M. M. Rogic and T. R. Demmin, J. Am. Chem. Soc., 100, 5472 (1978).CrossRefGoogle Scholar
  7. 7.
    G. La Monica, M. A. Angaroni, F. Cariati, S. Cenini, and A. Ardizzoia, Inorg. Chim. Acta, 148, 113 (1988).CrossRefGoogle Scholar
  8. 8.
    F. Chioccara, P. Di Gennaro, G. La Monica, R. Sebastiano, and B. Rindone, Tetrahedron, 47, 4429 (1991).CrossRefGoogle Scholar
  9. 9.
    D.-H. Lee, N. N. Murthy, and K. D. Karlin, Inorg. Chem., 35, 804 (1996).CrossRefGoogle Scholar
  10. 10.
    N. Wei, N. N. Murthy, Z. Tyekliir, and K. D. Karlin, Inorg. Chem., 33, 1177 (1994).CrossRefGoogle Scholar
  11. 11.
    Z. Tyeklhr, R. R. Jacobson, N. Wei, N. N. Murthy, J. Zubieta, and K. D. Karlin, J. Am. Chem. Soc., 115, 2611 (1993).Google Scholar
  12. 12.
    Z. Tyeklhr and K. D. Karlin, Acc. Chem. Res., 22, 241 (1989).CrossRefGoogle Scholar
  13. 13.
    K. D. Karlin, S. Kaderli, and A. D. Zuberbhler, Acc. Chem. Res., 30, 139 (1997).CrossRefGoogle Scholar
  14. 14.
    M. E. Winkler, K. Lerch, and E. I. Solomon, J. Am. Chem. Soc., 103, 7001 (1981).CrossRefGoogle Scholar
  15. 15.
    T. N. Sorrel, Tetrahedron, 45, 3 (1989).CrossRefGoogle Scholar
  16. 16.
    J. Ackermann, S. Buchler, and F. Meyer, Compt. Rend. Chimie, 10, 421 (2007).CrossRefGoogle Scholar
  17. 17.
    L. Casella, M. Gullotti, G. Pallanza, and L. Rigoni, J. Am. Chem. Soc., 110, 4221 (1988).CrossRefGoogle Scholar
  18. 18.
    J. Reim and B. Krebs, J. Chem. Soc., Dalton Trans., 3793 (1997).Google Scholar
  19. 19.
    S. Palavicini, A. Granata, E. Monzani, and S. Cassela, J. Am. Chem. Soc., 127, 18031 (2005).CrossRefGoogle Scholar
  20. 20.
    N. N. Murthy, M. Mahroof-Tahir, and K. D. Karlin, Inorg. Chem., 40, 628 (2001).CrossRefGoogle Scholar
  21. 21.
    P. K. Dhal, B. B. De, and S. Siviram, J. Mol. Catal. A: Chem., 177, 71 (2001).CrossRefGoogle Scholar
  22. 22.
    H. Li, Y.-Y. Luk, and M. Mrksish, Langmuir, 15, 4957 (1999).CrossRefGoogle Scholar
  23. 23.
    K. Marubayashi, S. Takizawa, T. T. Kawakusu, T. Arai, and H. Sasai, Org. Lett., 5, 4409 (2003).CrossRefGoogle Scholar
  24. 24.
    M. Brust, M. Walker, D. Bethell, D. J. Schiffrin, and R. Whyman, J. Chem. Soc., Chem. Commun., 801 (1994).Google Scholar
  25. 25.
    P. K. Ross and E. I. Solomon, J. Am. Chem. Soc., 113, 3246 (1991).CrossRefGoogle Scholar
  26. 26.
    M. J. Baldwin, P. K. Ross, J. E. Pate, Z. Tyekla, K. D. Karlin, and E. I. Solomon, J. Am. Chem. Soc., 113, 8671 (1991).CrossRefGoogle Scholar
  27. 27.
    M. J. Henson, P. Mukherjee, D. E. Root, T. D. P. Stack, and E. I. Solomon, J. Am. Chem. Soc., 121, 10332 (1999).CrossRefGoogle Scholar
  28. 28.
    H. Hayashi, S. Fujinami, S. Nagatomo, S. Ogo, M. Suzuki, A. Uehara, Y. Watanabe, and T. Kitagawa, J. Am. Chem. Soc., 122, 2124 (2000).CrossRefGoogle Scholar
  29. 29.
    A. Ulman, Chem. Rev., 96, 1533 (1996).CrossRefGoogle Scholar
  30. 30.
    C. Cooper, J. MacDonald, E. Soto, and W. McGimpsey, J. Am. Chem. Soc., 126, 1032 (2004).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2010

Authors and Affiliations

  • A. G. Majouga
    • 1
  • R. B. Romashkina
    • 1
  • A. S. Kashaev
    • 1
  • R. D. Rahimov
    • 1
  • E. K. Beloglazkina
    • 1
    Email author
  • N. V. Zyk
    • 1
  1. 1.Moscow M. V. Lomonosov State UniversityMoscowRussia

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