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Coumarin Appended Calix[4]arene as a Selective Fluorometric Sensor for Cu2+ Ion in Aqueous Solution

  • Quang, Duong Tuan (Department of Chemistry, Institute of Nanosensor & Biotechnology, Dankook University) ;
  • Jung, Hyo-Sung (Department of Chemistry, Institute of Nanosensor & Biotechnology, Dankook University) ;
  • Yoon, Jun-Hee (Department of Chemistry) ;
  • Lee, Su-Yeon (Department of Chemistry, Institute of Nanosensor & Biotechnology, Dankook University) ;
  • Kim, Jong-Seung (Department of Chemistry, Institute of Nanosensor & Biotechnology, Dankook University)
  • Published : 2007.04.20

Abstract

Keywords

References

  1. Mello, J. V.; Finney, N. S. J. Am. Chem. Soc. 2005, 127, 10124 https://doi.org/10.1021/ja043682p
  2. Guo, X. G.; Qian, X.; Jia, L. J. Am. Chem. Soc. 2004, 126, 2272 https://doi.org/10.1021/ja037604y
  3. Ono, A.; Togashi, H. Angew. Chem., Int. Ed. 2004, 43, 4300 https://doi.org/10.1002/anie.200454172
  4. Waggoner, A. S., In Applications of Fluorescence in the Biomedical Sciences; Taylor, D. L.; Liss, A. R., Eds.; Liss, New York, 1986
  5. Fluorescent Chemosensors for Ion and Molecular Recognition; Czarnik, A. W., Ed.; ACS Symposium Series 538; American Chemical Society: Washington, DC, 1993
  6. Czarnik, A. W. Acc. Chem. Res. 1994, 27, 302 https://doi.org/10.1021/ar00046a003
  7. Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 197
  8. Kim, S. K.; Lee, S. H.; Lee, J. Y.; Lee, J. Y.; Bartsch, R. A.; Kim, J. S. J. Am. Chem. Soc. 2004, 126, 16499 https://doi.org/10.1021/ja045689c
  9. Aoki, L.; Sakaki, T.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1992, 730
  10. Jin, T.; Ichikawa, K.; Koyama, T. J. Chem. Soc., Chem. Commun. 1992, 499
  11. Ji, H.-F.; Brown, G. M.; Dabestani, R. Chem. Commun. 1999, 609
  12. 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
  13. Lee, Y. O.; Choi, Y. H.; Kim, J. S. Bull. Korean Chem. Soc. 2007, 28, 151 https://doi.org/10.5012/bkcs.2007.28.1.151
  14. Lee, Y. O.; Lee, J. Y.; Quang, D. T.; Lee, M. H.; Kim, J. S. Bull. Korean Chem. Soc. 2006, 27, 1469 https://doi.org/10.5012/bkcs.2006.27.9.1469
  15. Park, H. R.; Oh, C.-H.; Lee, H.-C.; Choi, J. G.; Jung, B.-I.; Bark, K.-M. Bull. Korean Chem. Soc. 2006, 27(12), 2002 https://doi.org/10.5012/bkcs.2006.27.12.2002
  16. Leray, I.; Lefevre, J. P.; Delouis, J. F.; Delaire, J.; Valeur, B. Chem. Eur. J. 2001, 7(21), 4590 https://doi.org/10.1002/1521-3765(20011105)7:21<4590::AID-CHEM4590>3.0.CO;2-A
  17. Birks, J. B. Photophysics of Aromatic Molecules; Wiley- Interscience: London, 1970
  18. Lee, S. H.; Kim, S. H.; Kim, S. K.; Jung, J. H.; Kim, J. S. J. Org. Chem. 2005, 70, 9288 https://doi.org/10.1021/jo051302s
  19. Hecht, S.; Vladimirov, N.; Frechet, J. M. J. J. Am. Chem. Soc. 2001, 123, 18 https://doi.org/10.1021/ja003304u
  20. Valeur, B.; Leray, I. Coord. Chem. Rev. 2000, 205, 3 https://doi.org/10.1016/S0010-8545(00)00246-0
  21. Kim, J. S.; Noh, K. H.; Lee, S. H.; Kim, S. K.; Kim, S. K.; Yoon. J. J. Org. Chem. 2003, 68, 597 https://doi.org/10.1021/jo020538i
  22. Unob, F.; Asfari, Z.; Vicens, J. Tetrahedron Lett. 1998, 39, 2951 https://doi.org/10.1016/S0040-4039(98)00376-1
  23. Fabbrizzi, L.; Licchelli, M.; Pallavicini, P.; Perotti, A.; Taglietti, A.; Sacchi, D. Chem. Eur. J. 1996, 2, 167
  24. De Santis, G.; Fabbrizzi, L.; Licchelli, M.; Mangano, C.; Sacchi, D. Inorg. Chem. 1995, 34, 3581 https://doi.org/10.1021/ic00118a003
  25. Lee, S. H.; Kim, H. J.; Lee, Y. O.; Vicens, J.; Kim, J. S. Tetrahedron Lett. 2006, 47, 4373 https://doi.org/10.1016/j.tetlet.2006.04.093
  26. Choi, J. K.; Kim, S. H.; Yoon, J.; Lee, K.-H.; Bartsch, R. A.; Kim, J. S. J. Org. Chem. 2006, 71, 8011 https://doi.org/10.1021/jo060981j
  27. Suppan, P.; Ghoneim, N. In Solvatochromism; The Royal Society of Chemistry: Cambridge, UK, 1997; p 12
  28. Principles of Fluorescence Spectroscopy; Lakowicz, J. R., Ed.; Plenum Publishers Corporation: New York, 1999
  29. Boiocchi, M.; Fabbrizzi, L.; Licchelli, M.; Sacchi, D.; Vazquez, M.; Zampa, C. Chem. Commun. 2003, 1812
  30. Bolletta, F.; Costa, I.; Fabbrizzi, L.; Licchelli, M.; Montalti, M.; Pallavicini, P.; Prodi, L.; Zaccheroni, N. J. Chem. Soc. Dalton Trans. 1999, 1381
  31. Talanova, G. G.; Elkarim, N. S. A.; Talanov, V. S.; Bartsch, R. A. Anal. Chem. 1999, 71, 3106 https://doi.org/10.1021/ac990205u
  32. Chen, Q.-Y.; Chen, C.-F. Tetrahedron Lett. 2005, 46, 165 https://doi.org/10.1016/j.tetlet.2004.10.169
  33. Huheey, J. E.; Keiter, E. A.; Keiter, R. L. Inorganic Chemistry: Principles of Structure and Reactivity; HarperCollins College Publishers: New York, 1993
  34. Association constant was obtained using the computer program ENZFITTER, available from Elsevier-BIOSOFT, 68 Hills Road, Cambridge CB2 1LA, U.K.
  35. Connors, K. A. Binding Constants; Wiley: New York, 1987

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