Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Azo-functionalized Calix[4]arenes and Its Application to Chloride-selective Electrode as Ionophores

  • Lee, Hyo-Kyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Yeo, Hee-Kyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Park, Duck-Hee (vDepartment of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Jeon, Seung-Won (Department of Chemistry and Institute of Basic Science, Chonnam National University)
  • Published : 2003.12.20
Download PDF
⟨ Previous Next ⟩

Abstract

Azo-functionalized calix[4]arenes as ionophores for chloride-selective electrode, 5,11,17,23-Tetra-tert-butyl-25,27-bis[(N,N-dimethyl-aniline-azo-phenylthioureido)ethyl]oxy-26,28-dihydroxycalix[4]arene (4a) and 5,11,17,23-Tetra-tert-butyl-25,27-bis[(N,N-dimethyl-aniline-azo-phenylthioureido)ethyl]oxy-26,28-dimethoxycalix[4]arene (4b) were synthesized. The PVC membrane electrode based on azo-functionalized calix[4]arene 4a with o-NPOE exhibits a linear stable response over a wide concentration range ($1.5{\times}10^{-4}-1.0{\times}10^{-1}$) with a slope of -52.0 mV/decade and a detection limit of log[$Cl^-$] = -4.02. This ionophore-based membrane exhibited improved selectivity for chloride anion compared with classical Hofmeister series.

Keywords

References

  1. Dietrich, B. Pure Appl. Chem. 1993, 65, 1457. https://doi.org/10.1351/pac199365071457
  2. Atwood, F. L.; Holman, K. T.; Steed, J. W. Chem. Comm. 1996, 1401.
  3. Oka, S.; Sibazaki, Y.; Tahara, S. Anal. Chem. 1981, 53, 588. https://doi.org/10.1021/ac00227a007
  4. Park, S. B.; Matuszewski, W.; Meyerhoff, M. E.; Liu, Y. H.; Kadish, K. M. Electroanalysis 1991, 3, 909. https://doi.org/10.1002/elan.1140030906
  5. Wuthier, U.; Pham, H. V.; Zund, R.; Welti, D.; Funk, R. J. J.; Bezegh, A.; Ammann, D.; Pretsch, E.; Simon, W. Anal. Chem. 1984, 56, 535. https://doi.org/10.1021/ac00267a052
  6. Rothmaier, M.; Simon, W. Anal. Chim. Acta 1993, 271, 135. https://doi.org/10.1016/0003-2670(93)80560-8
  7. Ozawa, S.; Miyagi, H.; Shibata, Y.; Oki, N.; Kunitake, T.; Keller, W. E. Anal. Chem. 1996, 68, 4149. https://doi.org/10.1021/ac960526v
  8. Wegmann, D.; Weiss, H.; Ammann, D.; Morf, W. E.; Pretsch, E.; Sugahara, K.; Simon, W. Mikrochim. Acta 1984, III, 1.
  9. Kimura, K.; Matsute, M.; Yokoyama, M. Anal. Chim. Acta 1991, 252, 41. https://doi.org/10.1016/0003-2670(91)87194-C
  10. Kim, W.; Chung, S.; Park, S. B.; Lee, S. C.; Kim, C.; Sung, D. D. Anal. Chem. 1997, 69, 95.
  11. Sjoberg, P.; Bobacka, J.; Lewenstam, A.; Ivaska, A. Electroanalysis 1999, 11, 821. https://doi.org/10.1002/(SICI)1521-4109(199907)11:10/11<821::AID-ELAN821>3.0.CO;2-F
  12. Yoon, I. J.; Shin, J. H.; Paeng, I. R.; Nam, H.; Cha, G. S.; Paeng, K.-J. Anal. Chim. Acta 1998, 367, 175. https://doi.org/10.1016/S0003-2670(98)00174-3
  13. Malinowska, E.; Niedziolka, J.; Meyerhoff, M. E. Anal. Chim. Acta 2001, 432, 67. https://doi.org/10.1016/S0003-2670(00)01348-9
  14. Volf, R.; Shishkanova, T. V.; Matejka, P.; Hamplova, M.; Kral, V. Anal. Chim. Acta 1999, 381, 197. https://doi.org/10.1016/S0003-2670(98)00742-9
  15. Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, UK, 1998.
  16. Viens, J.; Bohmer, V. Calixarenes, a Versatile Class of Macrocyclic Compounds; Kluwer: Dordrecht, The Netherlands, 1990.
  17. Kang, S. O.; Oh, J. M.; Yang, Y. S.; Chun, J. C.; Jeon, S.; Nam, K. C. Bull. Korean Chem. Soc. 2002, 23, 145. https://doi.org/10.5012/bkcs.2002.23.1.145
  18. Jeong, H. S.; Choi, E. M.; Kang, S. O.; Nam, K. C.; Jeon, S. J. Electroanal. Chem. 2000, 485, 154. https://doi.org/10.1016/S0022-0728(00)00108-X
  19. Nam, K. C.; Kang, S. O.; Jeong, H. S.; Jeon, S. Tetrahedron Letters 1999, 40, 7343. https://doi.org/10.1016/S0040-4039(99)01505-1
  20. Jeon, S.; Yeo, H.; Jeong, H. S.; Oh, J. M.; Nam, K. C. Electroanalysis 2003, in press.
  21. Electroanalysis Jeon, S.;Yeo, H.;Jeong, H. S.;Oh, J. M.;Nam, K. C.

Cited by

  1. Calixarene-based Anion Receptors vol.17, pp.6, 2005, https://doi.org/10.1080/10610270500127089
  2. Ion and Molecular Recognition by Lower Rim 1,3-Di-conjugates of Calix[4]arene as Receptors vol.111, pp.8, 2011, https://doi.org/10.1021/cr1004524
  3. Synthesis of Azo-Functionalized Calix[4]arenes and Its Application to Chloride-Selective Electrode as Ionophores. vol.35, pp.15, 2004, https://doi.org/10.1002/chin.200415065
  4. Macrocycles containing azo groups: recognition, assembly and application vol.92, pp.1-2, 2018, https://doi.org/10.1007/s10847-018-0819-8
  5. Synthesis of two new p-tert-butylcalix[4]arene β-ketoimin derivatives for extraction of dichromate anion vol.63, pp.3-4, 2009, https://doi.org/10.1007/s10847-008-9513-6
  6. Fluorescent Sensing of Tetrahedral Anions with a Pyrene Urea Derivative of Calix[4]arene Chemosensor vol.30, pp.7, 2003, https://doi.org/10.5012/bkcs.2009.30.7.1675
  7. Tetrahedral Anions Selective Fluorescent Calix[6]arene Receptor Containing Urea and Pyrene Moieties vol.31, pp.12, 2003, https://doi.org/10.5012/bkcs.2010.31.12.3809
  8. Synthesis, FT-IR, FT-Raman, dispersive Raman and NMR spectroscopic study of a host molecule which potential applications in sensor devices vol.94, pp.None, 2003, https://doi.org/10.1016/j.saa.2012.03.070