Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Pyrene Appended Hg2+-selective Fluoroionophore Based upon Diaza-Crown Ether

  • Published : 2008.03.20
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Abstract

A new pyrene appended diaza-18-crown-6 ether derivative 1 has been prepared and its fluoroionophoric properties toward transition metal ions were investigated. Compound 1 exhibited a high Hg2+-selectivity over other transition metal ions as well as alkali and alkaline earth metal ions in aqueous acetonitrile solution. The ratiometric analysis of the monomer and excimer emissions of pyrene successfully signals the presence of Hg2+ ions. The detection limit for Hg2+ ions was found to be 3.1 ´ 10-6 M in 50% aqueous acetonitrile solution at pH 8.1. Competition experiments also suggest that the compound could be utilized as a selective and sensitive fluorescent chemosensor for the analysis of micromolar Hg2+ ions in physiological and environmental samples.

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References

  1. Desvergne, J. P.; Czarnik, A. W. Chemosensors of Ion and Molecule Recognition; Kluwer; Dordrecht, 1997
  2. Fluorescent Chemosensors for Ion and Molecule Recognition; Czarnik, A. W., Ed.; American Chemical Society: Washington, DC, 1992
  3. Shiraishi, Y.; Maehara, H.; Ishizumi, K.; Hirai, T. Org. Lett. 2007, 9, 3125 https://doi.org/10.1021/ol0713133
  4. Prodi, L.; Bargossi, C.; Montalti, M.; Zaccheroni, N.; Su, N.; Bradshaw, J. S.; Izatt, R. M.; Savage, P. B. J. Am. Chem. Soc. 2000, 122, 6769 https://doi.org/10.1021/ja0006292
  5. Descalzo, A. B.; Martinez-Manez, R.; Radeglia, R.; Rurack, K.; Soto, J. J. Am. Chem. Soc. 2003, 125, 3418 https://doi.org/10.1021/ja0290779
  6. Ros-Lis, J. V.; Martinez-Manez, R.; Rurack, K.; Sancenón, F.; Soto, J.; Spieles, M. Inorg. Chem. 2004, 43, 5183 https://doi.org/10.1021/ic049422q
  7. Yoon, S.; Albers, A. E.; Wong, A. P.; Chang, C. J. J. Am. Chem. Soc. 2005, 127, 16030 https://doi.org/10.1021/ja0557987
  8. Kim, S. H.; Song, K. C.; Ahn, S.; Kang, Y. S.; Chang, S.-K. Tetrahedron Lett. 2006, 47, 497 https://doi.org/10.1016/j.tetlet.2005.11.060
  9. Kim, S. H.; Youn, N. J.; Park, J. Y.; Choi, M. G.; Chang S.-K. Bull. Korean Chem. Soc. 2006, 27, 1553 https://doi.org/10.5012/bkcs.2006.27.10.1553
  10. Kim, J. S.; Quang, D. T. Chem. Rev. 2007, 107, 3780 https://doi.org/10.1021/cr068046j
  11. Nolan, E. M.; Lippard, S. J. J. Am. Chem. Soc. 2003, 125, 14270 https://doi.org/10.1021/ja037995g
  12. Yang, Y.-K.; Yook, K.-J.; Tae, J. J. Am. Chem. Soc. 2005, 127, 16760 https://doi.org/10.1021/ja054855t
  13. Zheng, H.; Qian, Z.-H.; Xu, L.; Yuan, F.-F.; Lan, L.-D.; Xu, J.-G. Org. Lett. 2006, 8, 859 https://doi.org/10.1021/ol0529086
  14. Nolan, E. M.; Racine, M. E.; Lippard, S. J. Inorg. Chem. 2006, 45, 2742 https://doi.org/10.1021/ic052083w
  15. Lee, M. H.; Wu, J.-S.; Lee, J. W.; Jung, J. H.; Kim, J. S. Org. Lett. 2007, 9, 2501 https://doi.org/10.1021/ol0708931
  16. de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515 https://doi.org/10.1021/cr960386p
  17. Kubo, K.; Sakurai, T. Chem. Lett. 1996, 959
  18. Kubo, K.; Kato, N.; Sakurai, T. Bull. Chem. Soc. Jpn. 1997, 70, 3041 https://doi.org/10.1246/bcsj.70.3041
  19. Kubo, K.; Ishige, R.; Sakurai, T. Heterocycles 1998, 48, 347 https://doi.org/10.3987/COM-97-8058
  20. Buhlmann, P.; Pretsch, E.; Bakker, E. Chem. Rev. 1998, 98, 1593 https://doi.org/10.1021/cr970113+
  21. Kubo, K.; Ishige, R.; Sakurai, T. Talanta 1999, 49, 339 https://doi.org/10.1016/S0039-9140(98)00380-4
  22. Habata, Y.; Akabori, S.; Bradshaw, J. S.; Izatt, R. M. Ind. Eng. Chem. Res. 2000, 39, 3465 https://doi.org/10.1021/ie0002327
  23. Gokel, G. W.; Leevy, W. M.; Weber, M. E. Chem. Rev. 2004, 104, 2723 https://doi.org/10.1021/cr020080k
  24. Bronson, R. T.;Michaelis, D. J.; Lamb, R. D.; Husseini, G. A.; Farnsworth, P. B.; Linford, M. R.; Izatt, R. M.; Bradshaw, J. S.; Savage, P. B. Org. Lett. 2005, 7, 1105 https://doi.org/10.1021/ol050027t
  25. Bell, T. W.; Hext, N. M. Chem. Soc. Rev. 2004, 33, 589
  26. Winnik, F. M. Chem. Rev. 1993, 93, 587. (b) Valeur, B.; Leray, I. Coord. Chem. Rev. 2000, 205, 3 https://doi.org/10.1016/S0010-8545(00)00246-0
  27. Kim, H. J.; Kim, S. H.; Quang, D. T.; Kim, J. H.; Suh, I.-H.; Kim, J. S. Bull. Korean Chem. Soc. 2007, 28, 811 https://doi.org/10.5012/bkcs.2007.28.5.811
  28. van der Veen, N. J.; Flink, S.; Deij, M. A.; Egberink, R. J. M.; van Veggel, F. C. J. M.; Reinhoudt, D. N. J. Am. Chem. Soc. 2000, 122, 6112 https://doi.org/10.1021/ja000713h
  29. Kim, J. H.; Hwang, A.-R.; Chang, S.-K. Tetrahedron Lett. 2004, 45, 7557 https://doi.org/10.1016/j.tetlet.2004.08.125
  30. Tsukube, H.; Adachi, H.; Morosawa, S. J. Chem. Soc. Perkin Trans.1 1989, 89
  31. Crown Ethers & Cryptands; Gokel, G. W. Ed.; Royal Society of Chemistry: Cambridge, 1991; p 113
  32. Gokel, G. W. Chem. Soc. Rev. 1992, 21, 39 https://doi.org/10.1039/cs9922100039
  33. Gokel, G. W.; Schall, O. F. Lariat Ethers in Comprehensive Supramolecular Chemistry; Elsevier: Oxford, 1996; pp 97-152
  34. Kuzmie, P. Anal. Biochem. 1996, 237, 260. The software Dynafit can be obtained from BioKin, Ltd. at http://www.biokin.com https://doi.org/10.1006/abio.1996.0238
  35. Shortreed, M.; Kopelman, R.; Kuhn, M.; Hoyland, B. Anal. Chem. 1996, 68, 1414 https://doi.org/10.1021/ac950944k
  36. Hay, R. W. Bio-inorganic Chemistry; Ellis Horwood: Chichester, 1984; p 10
  37. Hayashita, T.; Taniguchi, S.; Tanamura, Y.; Uchida, T.; Nishizawa, S.; Teramae, N.; Jin, Y. S.; Lee, J. C.; Bartsch, R. A. J. Chem. Soc. Perkin Trans 2 2000, 1003
  38. de Silva, A. P.; Fox, D. B.; Huxley, A. J. M.; Moody, T. S. Coord. Chem. Rev. 2000, 205, 41 https://doi.org/10.1016/S0010-8545(00)00238-1

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