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Fluorescent chemosensors for metal ions based on 3-(2-benzoxazol-5-yl)alanine skeleton

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Central European Journal of Chemistry

Abstract

The ability of new chelate ligands, benzoxazol-5-yl-alanine derivatives substituted in position 2 by heteroaromatic substituent, to form complexes with selected metal ions in acetonitrile are studied by means of absorption and steady-state and time-resolved fluorescence spectroscopy. Among the ligands studied, only azaaromatic derivatives form stable complexes with transition metal ions in the ground state. Their absorption bands are bathochromically shifted enabling to use those ligands as ratiometric sensors. The fluorescence of each ligand is quenched by metal ions, however, in the presence of Cd(II) and Zn(II) ions a new red shifted emission band is observed.

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References

  1. A.P. de Silva et al., Chem. Rev. 97, 1515 (1997)

    Article  Google Scholar 

  2. B. Valuer, I. Leray, Coord. Chem. Rev. 205, 3 (2000)

    Article  Google Scholar 

  3. J.F. Callan, A.P. de Silva, D.C. Magri, Tetrahedron 61, 8551 (2005)

    Article  CAS  Google Scholar 

  4. K. Rurack, Spectrochim. Acta A 57, 2161 (2001)

    Article  CAS  Google Scholar 

  5. C. Bargossi, M.C. Fiorini, M. Montalti, L. Prodi, N. Zaccheroni, Coord. Chem. Rev. 208, 17 (2000)

    Article  CAS  Google Scholar 

  6. E.A. Medlycott, G.S. Hanan, Coord. Chem. Rev. 250, 1763 (2006)

    Article  CAS  Google Scholar 

  7. F.N. Castellano, I.E. Pomestchenko, E. Shikhova, F. Hua, M.L. Muro, N. Rajapakse, Coord. Chem. Rev. 250, 1819 (2006)

    Article  CAS  Google Scholar 

  8. G. Xue et al., Tetrahedron 58, 4809 (2002)

    Article  CAS  Google Scholar 

  9. M.C. Kimber, I.B. Mahadevan, S.F. Lincoln, A.D. Ward, E.R.T. Tiekink, J. Org. Chem. 65, 8204 (2000)

    Article  CAS  Google Scholar 

  10. C.J. Fahrni, T.V. O`Halloran, J. Am. Chem. Soc. 121, 11448 (1999)

    Article  CAS  Google Scholar 

  11. G. Xue et al., Tetrahedron 57, 7623 (2001)

    Article  CAS  Google Scholar 

  12. J.M. Castagnetto, J.W. Canary, Chem. Commun. 203 (1998)

  13. Y. Mikata, M. Wakamatsu, S. Yano, Dalton Tran. 545 (2005)

  14. D.-Y. Wu et al., Dalton Trans 29, 3528 (2006)

    Article  CAS  Google Scholar 

  15. M.D. Shults, D.A. Pearce, B. Imperiali, J. Am. Chem. Soc. 125, 10591 (2003)

    Article  CAS  Google Scholar 

  16. K. Hanaoka, K. Kikuchi, H. Kojima, Y. Urano, T. Nagano, J. Am. Chem. Soc. 126, 12470 (2004)

    Article  CAS  Google Scholar 

  17. L. Xue, H.-H. Wang, X.-J. Wang, H. Jiang, Inorg. Chem. 47, 4310 (2008)

    Article  CAS  Google Scholar 

  18. Z. Xu, X. Qian, J. Cui, R. Zhang, Tetrahedron 62, 10117 (2006)

    Article  CAS  Google Scholar 

  19. K. Hanaoka, K. Kikuchi, H. Kojima, Y. Urano, T. Nagano, Angew. Chem. Int. Ed. 42, 2996 (2003)

    Article  CAS  Google Scholar 

  20. V. Balzani, G. Bergamini, F. Marchioni, P. Ceroni, Coord. Chem. Rev. 250, 1254 (2006)

    Article  CAS  Google Scholar 

  21. V. Amendola et al., Coord. Chem. Rev. 250, 273 (2006)

    Article  CAS  Google Scholar 

  22. K. Tanaka, H. Kumagai, H. Aoki, M. Deguchi, S. Iwata, J. Org. Chem. 66, 7328 (2001)

    Article  CAS  Google Scholar 

  23. J.-S. Youk, Y.H. Kim, E.-J. Kim, N.J. Youn, S.-K. Chang, Bull. Korean Chem. Soc. 25, 869 (2004)

    Article  CAS  Google Scholar 

  24. M.G.B. Drew et al., New J. Chem. 28, 462 (2004)

    Article  CAS  Google Scholar 

  25. K. Guzow et al., J. Photochem. Photobiol. A: Chem. 187, 87 (2007)

    Article  CAS  Google Scholar 

  26. K. Guzow, M. Szabelski, J. Malicka, J. Karolczak, W. Wiczk, Tetrahedron 58, 2201 (2002)

    Article  CAS  Google Scholar 

  27. SPECFIT/32 Global Analysis System for Windows, Spectrum Software Associates, Bio-Logic Science Instruments

  28. K. Rurack, R. Radeglia, Eur. J. Inorg. Chem. 2271 (2000)

  29. M.M. Henary, Y. Wu, C.J. Fahrni, Chem. Eur. J. 10, 3015 (2004)

    Article  CAS  Google Scholar 

  30. K. Guzow, M. Milewska, D. Wróblewski, A. Giełdoń, W. Wiczk, Tetrahedron 60, 11889 (2004)

    Article  CAS  Google Scholar 

  31. M. Milewska, A. Skwierawska, K. Guzow, D. Szmigiel, W. Wiczk, Inorg. Chem. Commun. 8, 947 (2005)

    Article  CAS  Google Scholar 

  32. B. Valeur, In: J.R. Lakowicz (Ed.), Principles of Fluorescent Probe Design for Ion Recognition. In Topics in Fluorescence Spectroscopy, Probe Design and Chemical Sensing (Plenum Press, New York, 1994) vol. 4, 21–48

    Google Scholar 

  33. R. Snyder, A.C. Testa, J. Phys. Chem. 88, 5948 (1984)

    Article  CAS  Google Scholar 

  34. H. Irving, R.J.P. Williams, Nature (London) 162, 746 (1948)

    Article  CAS  Google Scholar 

  35. M.M. Henary, C.J. Fahrni, J. Phys. Chem. A 106, 5210 (2002)

    Article  CAS  Google Scholar 

  36. M. Taki, J.L. Wolford, T.V. O’Halloran, J. Am. Chem. Soc. 126, 712 (2004)

    Article  CAS  Google Scholar 

  37. C.J. Chang, J. Jaworski, E.M. Nolan, M. Sheng, S.J. Lippard, Proc. Natl. Acad. Sci. USA 101, 1129 (2004)

    Article  CAS  Google Scholar 

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Correspondence to Wiesław Wiczk.

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Milewska, M., Guzow, K. & Wiczk, W. Fluorescent chemosensors for metal ions based on 3-(2-benzoxazol-5-yl)alanine skeleton. cent.eur.j.chem. 8, 674–686 (2010). https://doi.org/10.2478/s11532-010-0036-9

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  • DOI: https://doi.org/10.2478/s11532-010-0036-9

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