Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A Highly Selective and Sensitive Calcium(II)-Selective PVC Membrane Based on Dimethyl 1-(4-Nitrobenzoyl)-8-oxo-2,8-dihydro-1H-pyrazolo[5,1-a]isoindole-2,3-dicarboxylate as a Novel Ionophore

  • Published : 2006.06.20
Download PDF
⟨ Previous Next ⟩

Abstract

Dimethyl 1-(4-nitrobenzoyl)-8-oxo-2,8-dihydro-1H-pyrazolo[5,1-a]isoindole-2,3-dicarboxylate has been used as an ionophore and o-nitrophenyloctyl ether as a plasticizer in order to develop a poly(vinyl chloride)-based membrane electrode for calcium ion detection. The sensors exhibit significantly enhanced response towards calcium(II) ions over the concentration range $8.0{\times}10^{-7}\;1.0{\times}10^{-1}$ M at pH 3.0-11 with a lower detection limit of $5.0 {\times}10^{-7}$ M. The sensors display Nernstian slope of 29.5 ${\pm}$ 0.5 mV per decade for Ca(II) ions. Effects of plasticizers, lipophilic salts and various foreign common ions are tested. It has a fast response time within 10 s over the entire concentration range and can be used for at least 2 months without any divergence in potentials. The proposed electrode revealed good selectivity and response for $Ca^{2+}$ over a wide variety of other metal ions. The selectivity of the sensor is comparable with those reported for other such electrodes. The proposed sensor was successfully applied as an indicator electrode for the potentiometric titration of a Ca(II) solution, with EDTA.

Keywords

References

  1. Oesch, U.; Amman, D.; Simon, W. Clin. Chem. 1986, 32, 1448
  2. Arnold, M. A.; Meyerhoff, M. E. Anal. Chem. 1984, 56, 20R https://doi.org/10.1021/ac00269a003
  3. Davies, M. L.; Hamilton, C. J.; Murphy, S. M.; Tighe, B. J. Biomaterials 1992, 13, 971 https://doi.org/10.1016/0142-9612(92)90147-G
  4. Schaller, U.; Bakker, E.; Pretsch, E. Anal. Chem. 1995, 67, 3123 https://doi.org/10.1021/ac00114a005
  5. Schaller, U.; Bakker, E.; Spichiger, U. E.; Pretsch, E. Anal. Chem. 1994, 66, 391 https://doi.org/10.1021/ac00075a013
  6. Karaky, R.; Parker, D.; Teasdale, A. Anal. Chim. Acta 1993, 276, 353 https://doi.org/10.1016/0003-2670(93)80404-9
  7. Kumar, A.; Mittal, S. K. Sens. Actuators B 2004, 99, 340 https://doi.org/10.1016/j.snb.2003.11.033
  8. El-Jammal, A.; Bouklouze, A. A.; Patriarche, G. J.; Christian, G. D. Talanta 1991, 38, 929
  9. Dimitrakopoulos, T.; Farrell, J. R.; Iles, P. J. Electroanalysis 1996, 8, 391 https://doi.org/10.1002/elan.1140080417
  10. Suzuki, K.; Watanabe, K.; Matsumoto, Y.; Kobayashi, M.; Sato, S.; Siswanta, D.; Hisamoto, H. Anal. Chem. 1995, 67, 324 https://doi.org/10.1021/ac00098a016
  11. Kataky, R.; Parker, D.; Teasdale, A. Anal. Chim. Acta 1993, 276, 353 https://doi.org/10.1016/0003-2670(93)80404-9
  12. Liu, D.; Yuan, R.; Chen, W. C.; Yu, R. Q. Anal. Lett. 1994, 27, 1637 https://doi.org/10.1080/00032719408007423
  13. Saleh, M. B. Indian J. Chem., Sect. A 1991, 30, 444
  14. Ganjali, M. R.; Zamani, H. A.; Norouzi, P.; Adib, M.; Accedy, M. Acta. Chim. Slov. 2005, 52, 309
  15. Morf, W. E.; Seiler, K.; Rusterholz, B.; Simon, W. Anal. Chem. 1990, 62, 738 https://doi.org/10.1021/ac00206a018
  16. Hisamoto, H.; Watanabe, K.; Nakagawa, E.; Siswanta, S.; Shichi, Y.; Suzuki, K. Anal. Chim. Acta 1994, 299, 179 https://doi.org/10.1016/0003-2670(94)00351-3
  17. Shamsipur, M.; Khayatian, G.; Kazemi, S. Y.; Niknam, K.; Sharghi, H. J. Inclusion Phenom. 2001, 40, 303 https://doi.org/10.1023/A:1012737214492
  18. Islami, M. R.; Abedini-Torghabeh, J.; Fatemi, S. J.; Hassani, Z.; Amiry, A. Synlett 2004, 10, 1707
  19. Kamata, S.; Fukunaga, Y.; Murata, A. Anal. Chem. 1988, 60, 2464 https://doi.org/10.1021/ac00173a006
  20. Ganjali, M. R.; Pourjavid, M. R.; Rezapour, M.; Haghgoo, S. Sens. Actuators B 2003, 89, 21 https://doi.org/10.1016/S0925-4005(02)00422-7
  21. Zamani, H. A.; Rajabzadeh, G.; Ganjali, M. R.; Khatami, S. M. Electroanalysis 2005, 24, 2260
  22. Zamani, H. A.; Rajabzadeh, G.; Firouz, A.; Ariaii-Rad, A. A. J. Braz. Chem. Soc. 2005, 16, 1061 https://doi.org/10.1590/S0103-50532005000600025
  23. Zamani, H. A.; Ganjali, M. R.; Pooyamanesh, M. J. J. Braz. Chem. Soc. 2006, 1, 149
  24. Zamani, H. A.; Malekzadegan, F.; Ganjali, M. R. Anal. Chimi. Acta 2006, 555, 336 https://doi.org/10.1016/j.aca.2005.09.026
  25. Ganjali, M. R.; Zamani, H. A.; Norouzi, P.; Adib, M.; Rezapour, M.; Aceedy, M. Bull. Korean Chem. Soc. 2005, 26, 579 https://doi.org/10.5012/bkcs.2005.26.4.579
  26. Ganjali, M. R.; Matloobi, P.; Ghorbani, M.; Norouzi, P.; Salavati- Niasari, M. Bull. Korean Chem. Soc. 2005, 26, 38 https://doi.org/10.5012/bkcs.2005.26.1.038
  27. Saberyan, K.; Maragheh, M. G.; Ganjali, M. R. Bull. Korean Chem. Soc. 2004, 25, 460 https://doi.org/10.5012/bkcs.2004.25.4.460
  28. Ganjali, M. R.; Ghorbani, M.; Daftari, A.; Norouzi, P.; Pirelahi, H.; Dargahani, H. D. Bull. Korean Chem. Soc. 2004, 25, 172 https://doi.org/10.5012/bkcs.2004.25.2.172
  29. Ganjali, M. R.; Babaei, L. H.; Taghvaei-Ganjali, S.; Modjallal, A.; Shamsipur, M.; Hosseini, M.; Javanbakht, M. Bull. Korean Chem. Soc. 2004, 25, 177 https://doi.org/10.5012/bkcs.2004.25.2.177
  30. Ganjali, M. R.; Khoshdan, N.; Hashemi, O. R.; Sajjadi, S. A. S. Polish J. Chem. 2000, 74, 1389
  31. Ganjali, M. R.; Zargazi, M. H.; Mohajeri, A. Polish J. Chem. 2001, 75, 743
  32. Moller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618 https://doi.org/10.1103/PhysRev.46.618
  33. Head-Gordon, M.; Pople, J. A.; Frisch, M. J. Chem. Phys. Lett. 1988, 153, 503 https://doi.org/10.1016/0009-2614(88)85250-3
  34. S poner, J.; Berger, I.; S pac kova, N.; Leszczynski, J.; Hobza, P. J. Biolmol. Struct. Dyn. 2000, 11, 383
  35. Chalasinski, G.; Szczesniak, M. M. Chem. Rev. 1994, 94, 1723 https://doi.org/10.1021/cr00031a001
  36. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A. J.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al- Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 03, Revision A.7; Gaussian Inc.: Pittsburgh, PA, 2003
  37. Shamsipur, M.; Yousefi, M.; Ganjali, M. R. Anal. Chem. 2000, 72, 2391 https://doi.org/10.1021/ac991155w
  38. Shamsipur, M.; Yousefi, M.; Hosseini, M.; Ganjali, M. R. Anal. Lett. 2001, 34, 2249 https://doi.org/10.1081/AL-100107292
  39. Ganjali, M. R.; Naji, L.; Poursaberi, T.; Shamsipur, M.; Haghgoo, S. Anal. Chim. Acta 2003, 475, 59 https://doi.org/10.1016/S0003-2670(02)01226-6
  40. Shamsipur, M.; Yousefi, M.; Hosseini, M.; Ganjali, M. R. Anal. Chem. 2002, 74, 5538 https://doi.org/10.1021/ac0110451
  41. Ammann, E.; Pretsch, P.; Simon, W.; Lindner, E.; Bezegh, A.; Pungor, E. Anal. Chim. Acta 1991, 171, 119
  42. Petrukhin, O. M.; Kharitonov, A. B.; Urusov, Ye. I.; Schipulo, E. V.; Kruchinina, N. Ye.; Baulin, V. E. Anal. Chim. Acta 1997, 353, 11 https://doi.org/10.1016/S0003-2670(97)00376-0
  43. Rosatzin, T.; Bakker, E.; Suzuki, K.; Simon, W. Anal. Chim. Acta 1993, 280, 197 https://doi.org/10.1016/0003-2670(93)85122-Z
  44. Umezawa, Y.; Umezawa, K.; Sato, H. Pure Appl. Chem. 1995, 67, 507 https://doi.org/10.1351/pac199567030507

Cited by

  1. Fe(III) Ion‐Selective Membrane Electrode Based on 4‐Amino‐6‐methyl‐3‐methylmercapto‐1,2,4‐triazin‐5‐one vol.40, pp.8, 2007, https://doi.org/10.1080/00032710701380632
  2. Barium(II)-PVC Membrane Sensor Based on 4-4′-Methylenediantipyrine as a Neutral Carrier vol.41, pp.12, 2008, https://doi.org/10.1080/00032710802238077
  3. Magnesium-PVC Membrane Sensor Based on 4,5-Bis(Benzoylthio)-1,3-Dithiole-2-Thione vol.41, pp.14, 2008, https://doi.org/10.1080/00032710802363560
  4. Application of Novel Praseodymium (III) PVC‐Membrane Electrode for Determination of Pr(III) Ions in Soil and Sediment Samples vol.41, pp.5, 2008, https://doi.org/10.1080/00032710801934957
  5. Developments in the Field of Conducting and Non-conducting Polymer Based Potentiometric Membrane Sensors for Ions Over the Past Decade vol.8, pp.4, 2008, https://doi.org/10.3390/s8042331
  6. Erbium(III) PVC Membrane Ion-Selective Sensor based on 4-(2-Thiazolylazo)resorcinal vol.42, pp.2, 2009, https://doi.org/10.1080/00032710802585659
  7. Terbium(III) Ion-Selective Electrochemical Sensor Based on Hematoporphyrin vol.42, pp.2, 2009, https://doi.org/10.1080/00032710802585675
  8. -Bis(2-oxo-1,2-diphenylethylidene) ethanedihydrazide vol.42, pp.3, 2009, https://doi.org/10.1080/00032710802677092
  9. Determination of Fluoride Ions in Mouthwash Samples by a PVC Membrane Samarium(III) Sensor vol.42, pp.3, 2009, https://doi.org/10.1080/00032710802677142
  10. -Bis-[1-(2-hydroxy-1,2-diphenyl)ethylidene]ethanedihydrazide vol.42, pp.7, 2009, https://doi.org/10.1080/00032710902807821
  11. An efficient ab initio DFT and PCM assessment of the potentiometric selectivity of a salophen type Schiff base vol.20, pp.6, 2014, https://doi.org/10.1007/s00894-014-2258-9
  12. selective membrane electrode based on calcium-imprinted polymeric nanoparticles vol.40, pp.10, 2016, https://doi.org/10.1039/C6NJ00582A
  13. Dysprosium(III) Ion-Selective Electrochemical Sensor Based on 6-Hydrazino-1,5-diphenyl-6,7-dihydropyrazolo[3,4-d]pyrimidine-4(5H)-imine vol.72, pp.9, 2007, https://doi.org/10.1135/cccc20071189
  14. All-Solid-State Screen-Printed Sensors for Potentiometric Calcium(II) Determinations in Environmental Samples vol.09, pp.03, 2018, https://doi.org/10.4236/ajac.2018.93010
  15. Fabrication of a novel holmium(III) PVC membrane sensor based on 4-chloro-1,2-bis(2-pyridinecarboxamido)benzene as a neutral ionophore vol.37, pp.7, 2007, https://doi.org/10.1007/s10800-007-9321-5
  16. Fabrication of an iron(III)-selective PVC membrane sensor based on a bis-bidentate Schiff base ionophore vol.33, pp.8, 2008, https://doi.org/10.1007/s11243-008-9142-3
  17. Determination of Copper in Black, Red Pepper and the Waste Water Samples by a Highly Selective Sensitive Cu(II) Microelectrode Based on a New Hexadentates Schiff's Base vol.27, pp.9, 2006, https://doi.org/10.5012/bkcs.2006.27.9.1439
  18. A New Europium(III) PVC Membrane Potentiometric Sensor Based on 4-(2-Hydroxybenzylideneamino)-6-methyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one vol.80, pp.1, 2006, https://doi.org/10.1246/bcsj.80.172
  19. Fabrication of an iron(III) PVC-membrane sensor based on bis-benzilthiocarbohydrazide as a selective sensing material vol.29, pp.5, 2006, https://doi.org/10.1016/j.msec.2008.12.004
  20. Study of the influence of polymeric membrane composition on the sensitivity of acoustic wave sensors for metal analysis vol.150, pp.1, 2006, https://doi.org/10.1016/j.snb.2010.07.055
  21. Quantitative Analysis of Holmium Ion by a Ho3+ Ion‐Selective Sensor Based on a Symmetric Thio‐Schiff's Base vol.29, pp.7, 2006, https://doi.org/10.1002/cjoc.201180274