Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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N-Anthracenylmethyl Calix[4]azacrowns as New Fluorescent Ionophores

  • Yang, Seung-H. ;
  • Shon, Ok-J. ;
  • Park, Ki-M. ;
  • Lee, Shim-S. ;
  • Park, Ho-J. ;
  • Kim, Moon-J. ;
  • Lee, Joung-H. ;
  • Kim, Jong-S.
  • Published : 2002.11.20
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Abstract

Two novel calixarene-based fluoroionophores were synthesized. Their conformations were confirmed to 1,3-alternate by X-ray crystal structures. From CHEF by blocking the PET mechanism in fluorescence spectra, we observed $In^{3+}$ and $Pb^{2+}$ selectivity over other metal ions. For $In^{3+}$ion, calix[4]-bis-azacrown-5 showed about 20 times more sensitive than calix[4]-mono-azacrown-5 because the source of the binding selectivity comes from the calixarene framework and azacrown ligand by controlling the fluorescence and PET mechanisms as-sociated with the amine moiety.

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References

  1. Chemosensors of Ion and Molecule Recognition; Desvergne, J. P., Czarnik, A. W., Eds.; NATO ASI series, Kluwer Academic: Dordrecht, 1997.
  2. de Silva, A. P.; Gunaratne, H. Q.; Gunnlaugsson, N. T. A.; Huxley, T. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515. https://doi.org/10.1021/cr960386p
  3. Czarnik, A. W. Adv. Supramol. Chem. 1993, 3, 131.
  4. Fabbrizzi, S.; Poggi, A. Chem. Soc. Rev. 1995, 24, 197. https://doi.org/10.1039/cs9952400197
  5. de Santis, G.; di Casa, M.; Fabbrizzi, L.; Licchelli, M.; Mangano, C.; Pallavicini, P.; Perotti, A.; Poggi, A.; Sacchi, D.; Taglietti, A. In Transition Metals in Supramolecular Chemistry; Fabbrizzi, L., Poggi, A., Eds.; Kluwer: Dordrecht, 1994.
  6. Fabbrizzi, L.; Licchelli, M.; Pallavicini, P.; Sacchi, D.; Taglietti, A. Analyst. 1996, 121, 1763. https://doi.org/10.1039/an9962101763
  7. Tsien, R. Y. Fluorescent Chemosensors of Ion and Molecule Recognition; Czarnik, A. W., Ed.; ACS Symp. Ser. 538; American Chemical Society: Washington DC, 1993; p 130.
  8. Kuhn, M. A. Fluorescent Chemosensors of Ion and Molecule Recognition; Czarnik, A. W., Ed.; ACS Symp. Ser. 538; American Chemical Society: Washington DC, 1993; p 147.
  9. Desvergne, J.-P.; Fages, F.; Bouas-Laurent, H.; Marsau, P. Pure Appl. Chem. 1992, 64, 1231. https://doi.org/10.1351/pac199264091231
  10. Aoki, I.; Sakaki, T.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1992, 730.
  11. Bouas-Laurent, H.; Desvergne, J.-P.; Fages, F.; Marsau, P. Fluorescent Chemosensors of Ion and Molecule Recognition; Czarnik, A. W., Ed.; ACS Symp. Ser. 538; American Chemical Society: Washington DC, 1993; p 59.
  12. Bohmer, V. Angew. Chem. Int. Ed. Engl. 1995, 34, 713. https://doi.org/10.1002/anie.199507131
  13. Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989.
  14. Casnati, A.; Ungaro, R.; Asfari, Z.; Vicens, J. In Calixarenes 2001; Asfari, Z., Bohmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, Holland, 2001; pp 365-384.
  15. Kim, J. S.; Shon, O. J.; Ko, J. W.; Cho, M. H.; Yu, I. Y.; Vicens, J. J. Org. Chem. 2000, 65, 2386. https://doi.org/10.1021/jo9912754
  16. Kim, J. S.; Lee, W. K.; No, K.; Asfari, Z.; Vicens, J. Tetrahedron Lett. 2000, 41(18), 3345. https://doi.org/10.1016/S0040-4039(00)00382-8
  17. Kim, J. S.; Shon, O. J.; Sim, W.; Kim, S. K.; Cho, M. H.; Kim, J. G.; Suh, I. H.; Kim, D. W. J. Chem. Soc. Perkin Trans. 1 2001, 31.
  18. Kim, J. S.; Thuery, P.; Nierlich, M.; Rim, J. A.; Yang, S. H.; Lee, J. K.; Vicens, J. Bull. Korean Chem. Soc. 2001, 22(3), 321. https://doi.org/10.1007/BF02701504
  19. Casnati, A.; Pochini, A.; Ungaro, R.; Ugozzoli, F.; Arnaud-Neu, F.; Fanni, S.; Schwing, M.-J.; Egberink, R. J. M.; de Jong, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 2767. https://doi.org/10.1021/ja00115a012
  20. Jin, T.; Ichikawa, K.; Koyama, T. J. Chem. Soc., Chem. Commun. 1992, 499.
  21. Ji, H.-F.; Brown, G. M.; Dabestani, R. Chem. Commun. 1999, 609.
  22. Ji, H.-F.; Dabestani, R.; Brown, G. M.; Sachleben, R. A. Chem. Commun. 2000, 833.
  23. Kim, J. S.; Shon, O. J.; Rim, J. A.; Kim, S. K.; Yoon, J. J. Org. Chem. 2002, 67, 2348. https://doi.org/10.1021/jo010877w
  24. Kim, J. S.; Shon, O. J.; Lee, J. K.; Lee, S. H.; Kim, J. Y.; Park, K. M.; Lee, S. S. J. Org. Chem. 2002, 67, 1372-1375. https://doi.org/10.1021/jo0108921
  25. Kim, J. S.; Lee, W. K.; Kim, J. G.; Suh, I. H.; Yoon, J. Y.; Lee, J. H. J. Org. Chem. 2000, 65, 7215. https://doi.org/10.1021/jo000671f
  26. Connors, K. A. Binding Constants; Wiley: New York, 1987.
  27. Siemens: Structure Determination Programs. Version 5.03. in SHELXTL, Siemens Analytical X-ray Instruments Inc.: Madison, WI, 1996.

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