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N,N′-Bis(9-anthrylmethyl)diamines as fluorescent chemosensors for transition metal cations

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Abstract

N,N′-Bis(9-anthryl)-substituted diamines, imidazolidines, and hexahydropyrimidines were synthesized, and their luminescence properties and complexing ability were studied. N,N′-Bis(9-anthrylmethyl)ethane-1,2-diamine and N,N′-bis(9-anthrylmethyl)butane-1,4-diamine were found to be effective and selective PET chemosensors for Zn2+ and H+, respectively. 2-[1,3-Bis(9-anthrylmethyl)hexahydropyrimidin-2-yl]-6-methoxyphenol can be used as fluorescent chemosensor for mercury(II) cations.

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References

  1. Tolpygin, I.E., Bren’, V.A., Dubonosov, A.D., Minkin, and V.I., Rybalkin, V.P., Russ. J. Org. Chem., 2003, vol. 39, p. 1364.

    Article  CAS  Google Scholar 

  2. Gribanova, T.N., Dubonosov, A.D., Tolpygin, I.E., Rybalkin, V.P., Bren’, V.A., Minyaev, R.M., and Minkin, V.I., Russ. J. Org. Chem., 2005, vol. 41, p. 1175.

    Article  CAS  Google Scholar 

  3. Callan, J.F., de Silva, A.P., and Magri, D.C., Tetrahedron, 2005, vol. 61, p. 8551.

    Article  CAS  Google Scholar 

  4. Montalti, M., Prodi, L., and Zaccheroni, N., Handbook of Photochemistry and Photobiology, Nalwa, H.S., Ed., Stevenson Ranch, CA: American Scientific, 2003, vol. 2, p. 271.

    Google Scholar 

  5. de Silva, A.P., McClean, G.D., Moody, T.S., and Weir, S.M., Handbook of Photochemistry and Photobiology, Nalwa, H.S., Ed., Stevenson Ranch, CA: American Scientific, 2003, vol. 2, p. 217.

    Google Scholar 

  6. Bren’, V.A., Usp. Khim., 2001, vol. 70, p. 1152.

    Google Scholar 

  7. Valeur, B. and Leray, I., Coord. Chem. Rev., 2000, vol. 205, p. 3.

    Article  CAS  Google Scholar 

  8. de Silva, A.P., Gunaratne, H.Q.N., Gunnlaugsson, T., Huxley, A.J.M., McCoy, C.P., Rademacher, J.T., and Rice, T.E., Chem. Rev., 1997, vol. 97, p. 1515.

    Article  Google Scholar 

  9. Pina, F., Bernardo, M.A., and Garcia-España, E., Eur. J. Inorg. Chem., 2000, p. 2143.

  10. Pina, F., Lima, J.C., Lodeiro, C., de Melo, J.S., Diaz, P., Albelda, L.T., and Garcia-España, E., J. Phys. Chem. A, 2002, vol. 106, p. 8207.

    Article  CAS  Google Scholar 

  11. Czarnik, A.W., Acc. Chem. Res., 1994, vol. 27, p. 302.

    Article  CAS  Google Scholar 

  12. Sclafani, J.A., Maranto, M.T., Sisk, T.M., and Van Arman, S.A., Tetrahedron Lett., 1996, vol. 37, p. 2193.

    Article  CAS  Google Scholar 

  13. Fabbrizzi, L., Licchelli, M., Pallavicini, P., and Taglietti, A., Inorg. Chem., 1996, vol. 35, p. 1733.

    Article  CAS  Google Scholar 

  14. Chang, C.J., Nolan, E.M., Jaworski, J., Burdette, S.C., Shang, M., and Lippard, S., J. Chem. Biol., 2004, vol. 11, p. 203.

    Article  CAS  Google Scholar 

  15. Albelda, M.T., Diaz, P., Garcia-España, E., Lima, J.C., Lodeiro, C., de Melo, J.S., Parola, A.J., Pina, F., and Soriano, C., Chem. Phys. Lett., 2002, vol. 353, p. 63.

    Article  CAS  Google Scholar 

  16. Sancenon, F., Descalzo, A.B., Lloris, J.M., Martinez-Manez, R., Pardo, T., Segui, M.J., and Soto, J., Polyhedron, 2002, vol. 21, p. 1397.

    Article  CAS  Google Scholar 

  17. Fabbrizzi, L., Licchelli, M., Pallavicini, P., Perotti, A., Taglietti, A., and Sacehi, D., Chem., Eur. J., 1996, vol. 2, p. 75.

    CAS  Google Scholar 

  18. Amendola, V., Fabbrizzi, L., Mangano, C., Pallavicini, P., Perotti, A., and Taglietti, A., J. Chem. Soc., Dalton Trans., 2000, p. 185.

  19. Grabchev, I., Chovelon, J.-M., and Qian, X., New J. Chem., 2003, vol. 27, p. 337.

    Article  CAS  Google Scholar 

  20. Huston, M.E., Haider, K.W., and Czarnik, A.W., J. Am. Chem. Soc., 1988, vol. 110, p. 4460.

    Article  CAS  Google Scholar 

  21. Kubo, K., Sakurai, T., and Mori, A., Talanta, 1999, vol. 50, p. 73.

    Article  CAS  Google Scholar 

  22. Gunnlaugsson, T., Lee, T.C., and Parkesh, R., Tetrahedron, 2004, vol. 60, p. 11239.

    Article  CAS  Google Scholar 

  23. Geue, J.P., Head, N.J., Ward, D.L., and Lincoln, S.F., Aust. J. Chem., 2003, vol. 56, p. 917.

    Article  CAS  Google Scholar 

  24. Lin, Z., Priyadarshy, S., Bartko, A., and Waldeck, D.H., J. Photochem. Photobiol., A, 1997, vol. 110, p. 131.

    Article  CAS  Google Scholar 

  25. Hayashi, T., Mataga, N., Sakata, Y., Misumi, S., Morita, M., and Tanaka, J., J. Am. Chem. Soc., 1976, vol. 98, p. 5910.

    Article  CAS  Google Scholar 

  26. Lahlou, S., Bitit, N., and Desvergne, J.-P., J. Chem. Res., Synop., 1998, p. 302.

  27. Wasielewski, M.R., Minsek, D.W., Niemczyk, M.P., Svec, W.A., and Yang, N.C., J. Am. Chem. Soc., 1990, vol. 112, p. 2823.

    Article  CAS  Google Scholar 

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Original Russian Text © I.E. Tolpygin, V.P. Rybalkin, E.N. Shepelenko, N.I. Makarova, A.V. Metelitsa, Yu.V. Revinskii, A.V. Tsukanov, A.D. Dubonosov, V.A. Bren’, V.I. Minkin, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 3, pp. 390–394.

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Tolpygin, I.E., Rybalkin, V.P., Shepelenko, E.N. et al. N,N′-Bis(9-anthrylmethyl)diamines as fluorescent chemosensors for transition metal cations. Russ J Org Chem 43, 388–392 (2007). https://doi.org/10.1134/S1070428007030098

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  • DOI: https://doi.org/10.1134/S1070428007030098

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