Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Tetradiazo(o-carboxy)phenylcalix[4]arene for Determination of Pb2+ Ion

  • Tan, Le Van (Faculty of Chemical Engineering, Ho Chi Minh City University of Industry) ;
  • Quang, Duong Tuan (Department of Chemistry, Institute of Nanosensor & Biotechnology, Dankook University) ;
  • Lee, Min-Hee (Department of Chemistry, Institute of Nanosensor & Biotechnology, Dankook University) ;
  • Kim, Tae-Hyun (School of Chemistry, Seoul National University) ;
  • Kim, Ha-Suck (School of Chemistry, Seoul National University) ;
  • Kim, Jong-Seung (Department of Chemistry, Institute of Nanosensor & Biotechnology, Dankook University)
  • Published : 2007.05.20
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Abstract

A new azocalix[4]arene, 5,14,17,23-tetra[(2-benzoic acid)(azo)phenyl] calix[4]arene (2), has been prepared by hydrolysis of its ester derivative and characterized by 1H NMR, IR, UV-Vis spectroscopy and elemental analysis. Based on UV spectral changes, we found that 2 exhibits Pb2+ ion selectivity. In basic media, Pb2+ forms a 1:1 complex with the ligand. Beer's law is obeyed in the range of 2.0 × 10?6 ? 2.4 × 10?5 mol L?1 of Pb2+. The molar absorptivity (ε ) of 2-Pb2+ complex is 1.89 × 104 L mol?1 cm?1 at 440 nm, and the detection limit is 1.6 × 10?6 mol L?1.

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References

  1. Metivier, R.; Leray, I.; Valeur, B. Chem. Commun. 2003, 996
  2. Battistuzzi, G.; Borsari, M.; Menabue, L.; Saladini, M.; Sola, M. Inorg. Chem. 1996, 35, 4239 https://doi.org/10.1021/ic950599h
  3. Anonymous. ES&T Currents. Federal Environ. Sci. Techno; 1991, 25, 1187 https://doi.org/10.1021/es00019a609
  4. Ueno, K.; Imamura, T.; Cheng, K. L. Handbook of Organic Analytical Reagents; CRC Press: 2000
  5. Savvin, S. B.; Petrova, T. V.; Dzherayan, T. G.; Reichstat, M. M. Fresenius J. Anal. Chem. 1991, 4, 217
  6. Gutsche, C. D. In Calixarenes Revisited, Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: London, U. K., 1998
  7. Arnaud-Neu, F.; Asfari, Z.; Souley, B.; Vicens, J.; Thuery, P.; Nierlich, M. J. Chem. Soc., Perkin Trans. 2 2000, 495
  8. Prodi, L.; Bolletta, F.; Montalti, M.; Zaccheroni, N.; Casnati, A.; Sansone, F.; Ungaro, R. New J. Chem. 2000, 24, 155 https://doi.org/10.1039/a908693e
  9. Shinkai, S.; Araki, K.; Shibata, J.; Tsugawa, D.; Manabe, O. J. Chem. Soc. Perkin Trans. 1 1990, 3333
  10. Pearson, R. J. Am. Chem. Soc. 1963, 85, 3533 https://doi.org/10.1021/ja00905a001
  11. Shimizu, H.; Iwamoto, K.; Shinkai, S. Chem. Lett. 1991, 2147
  12. Yamamoto, H.; Ueda, K.; Sandanayake, K. R. A. S.; Shinkai, S. Chem. Lett. 1995, 497
  13. King, A. M.; Moore, C. P.; Sandanayake, K. R. A. S.; Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1992, 582
  14. Asfari, Z.; Bohmer, V.; Harrowfield, J.; Vicens, J., Eds.; Calixarenes 2001; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2001
  15. Mlika, R.; Ouada, H. B.; Renault, N. J.; Dumazet, I.; Lamartine, R.; Gamoudi, M.; Guillaud, G. Sens. Actuat. B 47 1998, 43 https://doi.org/10.1016/S0925-4005(98)00006-9
  16. Mlika, R.; Dumazet, I.; Ouada, H. B.; Renault, N. J.; Lamartine, R.; Gamoudi, M.; Guillaud, G. Sens. Actuat. B 2000, 628
  17. Arnaud-Neu, F.; Collins, E. M.; Deasy, M.; Ferguson, G.; Harris, S. J.; Kaitner, B.; Lough, A. J.; McKervey, M. A.; Marques, E.; Ruhl, B. L.; Schwing-Weill, M. J.; Seward, E. M. J. Am. Chem. Soc. 1989, 111(23), 8681
  18. Lee, Y. O.; Lee, J. Y.; Quang, D. T.; Lee, M. H.; Kim, J. S. Bull. Korean Chem. Soc. 2006, 27(12), 1469 https://doi.org/10.5012/bkcs.2006.27.9.1469
  19. Lee, Y. O.; Choi, Y. H.; Kim, J. S. Bull. Korean Chem. Soc. 2007, 28(1), 151 https://doi.org/10.5012/bkcs.2007.28.1.151
  20. 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
  21. Lee, S. H.; Kim, J. Y.; Ko, J.; Lee, J. Y.; Kim, J. S. J. Org. Chem. 2004, 69, 2902 https://doi.org/10.1021/jo049954o
  22. Lee, S. H.; Kim, S. K.; Bok, J. H.; Lee, S. H.; Yoon, J.; Lee, K.; Kim, J. S. Tetrahedron Lett. 2005, 46, 8163 https://doi.org/10.1016/j.tetlet.2005.09.117
  23. Chawla, H. M.; Nanda, M. Arkivoc 2003, 171
  24. Karci, F.; Sener, I.; Deligoz, H. Dyes and Pigments 2003, 59, 53 https://doi.org/10.1016/S0143-7208(03)00095-0
  25. Kao, T.-L.; Wang, C.-C.; Pan, Y.-T.; Shiao, Y.-J.; Yen, J.-Y.; Shu, C.-M.; Lee, G.-H.; Peng, S.-M.; Chung, W.-S. J. Org. Chem. 2005, 70(8), 2912 https://doi.org/10.1021/jo047880a
  26. Lu, J.; Chen, R.; He, X. J. Electroanal. Chem. 2002, 528, 33 https://doi.org/10.1016/S0022-0728(02)00840-9
  27. Ma, H. M.; Huang, Y. X.; Liang, S. C. Mikrochim. Acta 1998, 128, 181 https://doi.org/10.1007/BF01243047
  28. Lu, L.; Zhu, S.; Liu, X.; Xie, Z.; Yan, X. Ana. Chim. Acta 2005, 183, 535
  29. Ma, Q.; Ma, H.; Su, M.; Wang, Z.; Nie, L.; Liang, S. Anal. Chim. Acta 2001, 439, 73 https://doi.org/10.1016/S0003-2670(01)01009-1
  30. Kim, T. H.; Kim, S. H.; Tan, L. V.; Seo, Y. J.; Park, S. Y.; Kim, H.; Kim, J. S. Talanta 2007, 71, 1294 https://doi.org/10.1016/j.talanta.2006.06.035
  31. Benesi, H. A.; Hildebrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703 https://doi.org/10.1021/ja01176a030

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