Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Voltammetric Studies of Diazocalix[4]crown-6 for Metal Ion Sensing

  • Received : 2010.09.06
  • Accepted : 2010.09.20
  • Published : 2010.12.20
Download PDF
⟨ Previous Next ⟩

Abstract

The complex formation between diazocalix[4]dipropyl (1) and diazocalix[4]crown-6 ether (2) with alkali, alkaline earth and transition metal ions was investigated by voltammetry. Electrochemical properties of compounds 1 and 2 and their selectivity toward metal ions were evaluated in $CH_3CN$ solution by comparison of voltammetric behaviors of two phenols in each compound. Compounds 1 and 2 showed almost same voltammetric behavior which is two irreversible oxidation peaks caused by intramolecular hydrogen bonding between two phenols in 1 and 2. While, however, upon interacting with various metal ions, 1 with two propyl ether groups showed no significant changes in voltammetry, 2 with crown ether group caused significant voltammetric changes upon the addition of $Ba^{2+}$ to 2. Their behavior is closely related to the complex formation by entrapment of metal ion into crown ether cavity, and ion-dipole interaction between metal ion and two phenolic groups in calix[4]crown-6.

Keywords

References

  1. Gutsche, C. D. Royal Society of Chemistry (Great Britain), Calixarenes: an introduction, 2nd ed.; RSC Publishing: Cambridge, 2008; p 276.
  2. Mandolini, L.; Ungaro, R. Calixarenes in Action; Imperial College Press: Distributed by World Scientific Pub. Co.: London River Edge, NJ, 2000; p 271.
  3. Lee, S. H.; Kim, H. J.; Lee, Y. O.; Vicens, J.; Kim, J. S. Tetrahedron Lett. 2006, 47, 4373-4376. https://doi.org/10.1016/j.tetlet.2006.04.093
  4. Lee, M. H.; Quang, D. T.; Jung, H. S.; Yoon, J.; Lee, C. H.; Kim, J. S. J. Org. Chem. 2007, 72, 4242-4245. https://doi.org/10.1021/jo070361y
  5. Bew, S. P.; Brimage, R. A.; L'Hermite, N.; Sharma, S. V. Org. Lett. 2007, 9, 3713-3716. https://doi.org/10.1021/ol071047t
  6. Gaeta, C.; Troisi, F.; Neri, P. Org. Lett. 2010, 12, 2092-2095. https://doi.org/10.1021/ol100578z
  7. Kim, J. S.; Lee, S. Y.; Yoon, J.; Vicens, J. Chem. Commun. 2009, 4791-4802.
  8. Metay, E.; Duclos, M. C.; Pellet-Rostaing, S.; Lemaire, M.; Kannappan, R.; Bucher, C.; Saint-Aman, E.; Chaix, C. Tetrahedron 2009, 65, 672-676. https://doi.org/10.1016/j.tet.2008.11.032
  9. Rozhenko, A. B.; Schoeller, W. W.; Letzel, M. C.; Decker, B.; Agena, C.; Mattay, J. Chem.-Eur. J. 2006, 12, 8995-9000. https://doi.org/10.1002/chem.200501520
  10. Shahgaldian, P.; Sclotti, M. A.; Pieles, U. Langmuir 2008, 24, 8522-8526. https://doi.org/10.1021/la801083h
  11. Asfari, Z. Calixarenes 2001; Kluwer Academic Publishers: Dordrecht, Boston, 2001; p 683.
  12. Kim, H. J.; Kim, S. H.; Kim, J. H.; Anh, L. N.; Lee, J. H.; Lee, C. H.; Kim, J. S. Tetrahedron Lett. 2009, 50, 2782-2786. https://doi.org/10.1016/j.tetlet.2009.03.149
  13. Lee, J. W.; Park, S. Y.; Cho, B. K.; Kim, J. S. Tetrahedron Lett. 2007, 48, 2541-2546. https://doi.org/10.1016/j.tetlet.2007.02.026
  14. Kim, J. Y.; Kim, G.; Kim, C. R.; Lee, S. H.; Lee, J. H.; Kim, J. S. J. Org. Chem. 2003, 68, 1933-1937. https://doi.org/10.1021/jo020684o
  15. Park, S. Y.; Yoon, J. H.; Hong, C. S.; Souane, R.; Kim, J. S.; Matthews, S. E.; Vicens, J. J. Org. Chem. 2008, 73, 8212-8218. https://doi.org/10.1021/jo8012918
  16. Choi, J. K.; No, K.; Lee, E. H.; Kwon, S. G.; Kim, K. W.; Kim, J. S. Supramol. Chem. 2007, 19, 283-286. https://doi.org/10.1080/10610270701258386
  17. Choi, J. K.; Kim, S. H.; Yoon, J.; Lee, K. H.; Bartsch, R. A.; Kim, J. S. J. Org. Chem. 2006, 71, 8011-8015. https://doi.org/10.1021/jo060981j
  18. Lee, S. H.; Kim, S. K.; Bok, J. H.; Lee, S. H.; Yoon, J.; Lee, K.; Kim, J. S. Tetrahedron Lett. 2005, 46, 8163-8167. https://doi.org/10.1016/j.tetlet.2005.09.117
  19. Kim, S. K.; Lee, S. H.; Lee, J. Y.; Lee, J. Y.; Bartsch, R. A.; Kim, J. S. J. Am. Chem. Soc. 2004, 126, 16499-16506. https://doi.org/10.1021/ja045689c
  20. Kim, T. H.; Kim, J. S.; Kim, H. J. Electroanal. Chem. 2008, 615, 103-109. https://doi.org/10.1016/j.jelechem.2007.11.034
  21. Choi, Y.; Kim, H.; Lee, J. K.; Lee, S. H.; Lim, H. B.; Kim, J. S. Talanta 2004, 64, 975-980. https://doi.org/10.1016/j.talanta.2004.04.015
  22. Sessler, J. L.; Kim, S. K.; Gross, D. E.; Lee, C. H.; Kim, J. S.; Lynch, V. M. J. Am. Chem. Soc. 2008, 130, 13162-13166. https://doi.org/10.1021/ja804976f
  23. Bouhroum, S.; Kim, J. S.; Lee, S. W.; Thuery, P.; Yap, G.; Arnaud-Neu, F.; Vicens, J. J. Incl. Phenom. Macro. 2008, 62, 239-250. https://doi.org/10.1007/s10847-008-9463-z
  24. Kim, S. K.; Lee, J. K.; Lim, J. M.; Kim, J. W.; Kim, J. S. Bull. Korean Chem. Soc. 2004, 25, 1247-1250. https://doi.org/10.5012/bkcs.2004.25.8.1247
  25. Kim, S. K.; Lee, J. K.; Lee, S. H.; Lim, M. S.; Lee, S. W.; Sim, W. B.; Kim, J. S. J. Org. Chem. 2004, 69, 2877-2880. https://doi.org/10.1021/jo035567n
  26. Kim, S. K.; Kim, S. H.; Kwon, S. G.; Lee, E. H.; Lee, S. H.; Kim, J. S. Bull. Korean Chem. Soc. 2004, 25, 1244-1246. https://doi.org/10.5012/bkcs.2004.25.8.1244
  27. Lee, J. K.; Kim, S. K.; Bartsch, R. A.; Vicens, J.; Miyano, S.; Kim, J. S. J. Org. Chem. 2003, 68, 6720-6725. https://doi.org/10.1021/jo034666y
  28. Kaifer, A. E.; Gomez-Kaifer, M. Supramolecular Electrochemistry; Wiley-VCH: Weinheim, New York, 1999; p 241.
  29. Dong, Y. Y.; Kim, T. H.; Kim, H. J.; Lee, M. H.; Lee, S. Y.; Mahajan, R. K.; Kim, H.; Kim, J. S. J. Electroanal. Chem. 2009, 628, 119-124. https://doi.org/10.1016/j.jelechem.2009.01.015
  30. Kim, T. H.; Kim, S. H.; Van Tan, L.; Dong, Y. Y.; Kim, H.; Kim, J. S. Talanta 2008, 74, 1654-1658. https://doi.org/10.1016/j.talanta.2007.10.033

Cited by

  1. -Selective Azocalix[4]arene Bearing p-Carboxyl group vol.34, pp.11, 2013, https://doi.org/10.5012/bkcs.2013.34.11.3377
  2. Macrocycles containing azo groups: recognition, assembly and application vol.92, pp.1-2, 2018, https://doi.org/10.1007/s10847-018-0819-8
  3. Effect of Crown Ring Size and Upper Moiety on the Extraction of s-Block Metals by Ionizable Calixcrown Nano-baskets vol.32, pp.11, 2010, https://doi.org/10.5012/bkcs.2011.32.11.3979
  4. Calixarene-based anionic receptors: highlights from 2011 vol.25, pp.7, 2010, https://doi.org/10.1080/10610278.2013.794277