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Electrochemical investigation of nano-baskets of calix[4]-1,3-crowns-5,6 complexes

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Abstract

Four nano-baskets of calixarene including cone 25,27-di(carboxymethoxy)calix[4]arene-crown-5, 1,3-alternate 25,27-di[carboxymethoxy]-calix[4]arene-crown-5, cone 25,27-bis[carboxymethoxy]calix[4]arene-crown-6 and 1,3-alternate 25,27-di[carboxymethoxy]-calix[4]arene-crown-6 were synthesized and their binding abilities towards alkali and alkaline earth metals as well as some lanthanides were studied using differential pulse voltammetry. The novelty of this study was investigation of those macrocyclic complexes by voltammetric behaviors of two acidic moieties in each scaffold during complexation of crown ether ring. Their voltammetric behaviors were closely related to the complex formation by entrapment of cation into crown ether cavity and ion–dipole interaction between cation and acidic moieties in calixcrowns. The results revealed the selective changes in voltammetric behavior of synthesized scaffolds toward the cations. Moreover, the position of crown ether in 1,3-alternate instead of cone enhanced the domain of binding ability to more cations. Furthermore, it was shown that those carboxylic acid moieties, which were far from the crown ether ring in the 1,3-alternate, did not affected by encapsulated cations in the coordination space of crown ether and showed no voltammetric behavior.

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References

  1. Mokhtari, B., Pourabdollah, K., Dalali, N.: Analytical applications of calixarenes from 2005 up-to-date. J. Incl. Phenom. Macrocycl. Chem. 69(1–2), 1–55 (2011)

    Article  CAS  Google Scholar 

  2. Mokhtari, B., Pourabdollah, K., Dalali, N.: Molecule and ion recognition of nano-baskets of calixarenes since 2005. J. Coord. Chem. 64(5), 743–794 (2011)

    Article  CAS  Google Scholar 

  3. Mokhtari, B., Pourabdollah, K., Dallali, N.: A review of calixarene applications in nuclear industries. J. Radioanal. Nucl. Chem. 287(3), 921–934 (2011)

    Article  CAS  Google Scholar 

  4. Mokhtari, B., Pourabdollah, K., Dalali, N.: Applications of nano-baskets of calixarenes in chromatography. Chromatographia 73(9–10), 829–847 (2011)

    Article  CAS  Google Scholar 

  5. Mokhtari, B., Pourabdollah, K.: Advances in binding ability and extractive applications of nano-baskets of calixarene. Asian J. Chem. 23(11), 4714–4734 (2011)

    Google Scholar 

  6. Salorinne, K., Nissinen, M.: Calixcrowns: synthesis and properties. J. Incl. Phenom. Macrocycl. Chem. 61(1–2), 11–27 (2008)

    Article  CAS  Google Scholar 

  7. Kim, J.S., Vicens, J.: Progress of calixcrowns chemistry. J. Incl. Phenom. Macrocycl. Chem. 63(1–2), 189–193 (2009)

    Article  CAS  Google Scholar 

  8. Lamare, V., Dozol, J.F., Ugozzoli, F., Casnati, A., Ungaro, R.: X-ray crystal structures and molecular modelling studies of calix[4]dibenzocrowns-6 and their alkali metal cation complexes. Eur. J. Org. Chem. 1998(8), 1559–1568 (1998)

    Article  Google Scholar 

  9. Mokhtari, B., Pourabdollah, K.: Competitive solvent extraction of alkaline earth metals by ionizable nano-baskets of calixarene. Supramol. Chem. 23, 696–702 (2011)

    Article  CAS  Google Scholar 

  10. Mokhtari, B., Pourabdollah, K.: Medical applications of nano-baskets. J. Coord. Chem. 64, 3189–3204 (2011)

    Article  CAS  Google Scholar 

  11. Mokhtari, B., Pourabdollah, K.: Effect of crown size and upper moieties in nano-baskets of diacid calix[4]arene-1,2-crowns-3,4,5,6 on the extraction of s-block metals. J. Coord. Chem. 64, 3081–3091 (2011)

    Article  CAS  Google Scholar 

  12. Mokhtari, B., Pourabdollah, K.: Solvent extraction of alkali metals by di-ionizable nano-baskets. J. Coord. Chem. 64, 4029–4053 (2011)

    Article  CAS  Google Scholar 

  13. Mokhtari, B., Pourabdollah, K.: Investigation of ionizable nano-baskets of calix[4]-1,2-crown-3 by differential pulse voltammetry. J. Coord. Chem. 64, 4079–4087 (2011)

    Article  CAS  Google Scholar 

  14. Mokhtari, B., Pourabdollah, K.: Structure optimization of di-ionizable calixarene nano-baskets for competitive solvent extraction of alkali and alkaline earth metals. Bull. Korean Chem. Soc. 32, 3855–3860 (2011)

    Article  CAS  Google Scholar 

  15. Mokhtari, B., Pourabdollah, K.: Effect of crown ring size and upper moiety on the extraction of s-block metals by ionizable calixcrown nano-baskets. Bull. Korean Chem. Soc. 32, 3979–3990 (2011)

    Article  CAS  Google Scholar 

  16. Mokhtari, B., Pourabdollah, K.: Inclusion desalination of alkali metal cations by emulsion liquid membranes and nano-baskets of p-tert-calix[4]arene bearing di-[n-(x)sulfonyl carboxamide] and di-(1-propoxy) in para-cone conformation. Desalination 292, 1–8 (2012)

    Article  CAS  Google Scholar 

  17. Mokhtari, B., Pourabdollah, K.: Determination of salbutamol in livestock by nano-mediated bonded-phases: nano-baskets of calixarene in partial-cone conformation. J. Chilean Chem. Soc. 58, 827–831 (2012)

    Google Scholar 

  18. Mokhtari, B., Pourabdollah, K.: Applications of calixarene nano-baskets in pharmacology. J. Incl. Phenom. Macrocycl. Chem. 73, 1–15 (2012). doi:10.1007s10847-011-0062-z

    Article  CAS  Google Scholar 

  19. Mokhtari, B., Pourabdollah, K.: Applications of nano-baskets in drug development: high solubility and low toxicity. Drug Chem. Toxicol. (2012). doi:10.3109/01480545.2011.653490

    Google Scholar 

  20. Mokhtari, B., Pourabdollah, K.: Binding and extraction of alkali and alkaline earth metals by nano-baskets of calix[4]arene-1,2-crown-3 conformers. J. Incl. Phenom. Macrocycl. Chem. 73, 269–277 (2012). doi:10.1007/s10847-011-0052-1

    Article  CAS  Google Scholar 

  21. Mokhtari, B., Pourabdollah, K.: Binding mechanisms of nano-baskets towards alkali metals. Isothermal titration calorimetric study. J. Therm. Anal. Calorim. (2012). doi:10.1007/s10973-011-2014-7

    Google Scholar 

  22. Mokhtari, B., Pourabdollah, K.: Extraction of vanadyl porphyrins in crude oil by inclusion dispersive liquid–liquid microextraction and nano-baskets of calixarene. J. Incl. Phenom. Macrocycl. Chem. (2012). doi:10.1007/s10847-011-0099-z

    Google Scholar 

  23. Mokhtari, B., Pourabdollah, K.: Binding survey of ionizable calix[4]-1,2-crown-3 nano-baskets by differential pulse voltammetry. Electroanalysis 24(2), 219–223 (2012)

    Google Scholar 

  24. Mokhtari, B., Pourabdollah, K.: Binding study of ionizable calix[4]-1,3-crowns-5,6 nano-baskets by differential pulse voltammetry. J. Electrochem. Soc. 159(3), K61–K65 (2012)

    Google Scholar 

  25. Mokhtari, B., Pourabdollah, K.: Dispersive enhancement in liquid–liquid microextraction by dual supramolecular role of nano-baskets. Supramol. Chem. 24(4), 255–263 (2012)

    Google Scholar 

  26. Mokhtari, B., Pourabdollah, K.: Chromatographic separation of clenbuterol by bonded-phases bearing nano-baskets of p-tert-calix[4]-1,2-crown-3; -crown-4; -crown-5; and -crown-6. J. Sci. Food Agric. (2012). doi:10.1002/jsfa.5688

    Google Scholar 

  27. Mokhtari, B., Pourabdollah, K.: Inclusion extraction of alkali metals by emulsion liquid membranes and nano-baskets of p-tert-calix[4]arene bearing di-[N-(X)sulfonyl carboxamide] and di-(1-propoxy) in ortho-cone conformation. Bull. Korean Chem. Soc. 33(5), 1509–1516 (2012)

    Google Scholar 

  28. Mokhtari, B., Pourabdollah, K.: Extraction of s-block metals by nano-baskets of calix[4]crown-3. Can. J. Chem. 90(6), 560–566 (2012)

    Google Scholar 

  29. Mokhtari, B., Pourabdollah, K.: Emulsion liquid membranes for effective inclusion extraction of alkali metals by nano-baskets of calixarene. Synth. React. Inorg. Metal-Org. Nano-Metal Chem. (2012). doi:10.1080/15533174.2012.654879

    Google Scholar 

  30. Zheng, H., Yan, Z., Dong, H., Ye, B.: Simultaneous determination of lead and cadmium at a glassy carbon electrode modified with Langmuir–Blodgett film of p-tert-butylthiacalix[4]arene. Sens. Actuators B 120(2), 603–609 (2007)

    Article  CAS  Google Scholar 

  31. Dong, H., Zheng, H., Lin, L., Ye, B.: Determination of thallium and cadmium on a chemically modified electrode with Langmuir–Blodgett film of p-allylcalix[4]arene. Sens. Actuators B 115(1), 303–308 (2006)

    Article  CAS  Google Scholar 

  32. Raoof, J.B., Ojani, R., Alinezhad, A., Rezaie, S.Z.: Differential pulse anodic stripping voltammetry of silver(I) using p-isopropylcalix[6]arene modified carbon paste electrode. Monatshefte Chem. 141(3), 279–284 (2010)

    Article  CAS  Google Scholar 

  33. Wang, L., Zhao, B.T., Ye, B.X.: Electrochemical properties of electrode modified with Langmuir–Blodgett film of p-tertbutylcalix[4]arene derivatives and its application in determining of silver. Electroanalysis 19(9), 923–927 (2007)

    Article  CAS  Google Scholar 

  34. Dong, H., Lin, L., Zheng, H., Zhao, G., Ye, B.: Electrode modified with Langmuir–Blodgett (LB) film of calixarenes for preconcentration and stripping analysis of Hg(II). Electroanalysis 18(12), 1202–1207 (2006)

    Article  CAS  Google Scholar 

  35. Wang, F., Liu, J., Wu, Y.J., Gao, Y.M., Huang, X.F.: Anodic stripping voltammetric determination of mercury(II) in water using a 4-tert-butyl-1-(ethoxycarbonylmethoxy)thiacalix[4]arene modified glassy carbon electrode. J. Chin. Chem. Soc. 56, 778–784 (2009)

    CAS  Google Scholar 

  36. Canpolat, E.C., Sar, E., Coskun, N.Y., Cankurtaran, H.: Determination of trace amounts of copper in tap water samples with a calix[4]arene modified carbon paste electrode by differential pulse anodic stripping voltammetry. Electroanalysis 19(10), 1109–1115 (2007)

    Article  CAS  Google Scholar 

  37. Shamsipur, M., Miranbeigi, A.A., Teymouri, M., Rasoolipour, S., Asfari, Z.: Highly sensitive and selective poly(vinyl chloride)-membrane potentiometric sensors based on a calix[4]arene derivative for 2-furaldehyde. Anal. Chem. 81(16), 6789–6796 (2009)

    Article  CAS  Google Scholar 

  38. Snejdarkova, M., Poturnayova, A., Rybar, P., Lhotak, P., Him, M., Flidrova, K., Hianik, T.: High sensitive calixarene-based sensor for detection dopamine by electrochemical and acoustic methods. Bioelectrochemistry 80(1), 55–61 (2010)

    Article  CAS  Google Scholar 

  39. Vaze, V.D., Srivastava, A.K.: Electrochemical behavior of folic acid at calixarene based chemically modified electrodes and its determination by adsorptive stripping voltammetry. Electrochim. Acta 53, 1713–1721 (2007)

    Article  CAS  Google Scholar 

  40. Zhang, H.L., Liu, Y., Lai, G.S., Yu, A.M., Huang, Y.M., Jin, C.M.: Calix[4]arene crown-4 ether modified glassy carbon electrode for electrochemical determination of norepinephrine. Analyst 134, 2141–2146 (2009)

    Article  CAS  Google Scholar 

  41. Lai, G.S., Zhang, H.L., Jin, C.M.: Electrocatalysis and voltammetric determination of dopamine at a calix[4]arene crown-4 ether modified glassy carbon electrode. Electroanalysis 19(4), 496–501 (2007)

    Article  CAS  Google Scholar 

  42. Liu, H., Zhao, G., Wen, L., Ye, B.: Simultaneous voltammetric determination of epinephrine and serotonin at a p-tetra-butyl calix[6]arene-l-histidine chemically modified electrode. J. Anal. Chem. 61(11), 1104–1107 (2006)

    Article  CAS  Google Scholar 

  43. Amiri, A., Choi, E.Y., Kim, H.J.: Development and molecular recognition of calixcrownchip as an electrochemical ALT immunosensor. J. Incl. Phenom. Macrocycl. Chem. 66(1–2), 185–194 (2010)

    Article  CAS  Google Scholar 

  44. Kotkar, R.M., Srivastava, A.K.: Electrochemical behavior of nicotinamide using carbon paste electrode modified with macrocyclic compounds. J. Incl. Phenom. Macrocycl. Chem. 60(3–4), 271–279 (2008)

    Article  CAS  Google Scholar 

  45. Sosovska, O., Korpan, Y., Vocanson, F., Jaffrezic-Renault, N.: Conductometric chemosensors based on calixarenes for determination of amines and amino acids. Sens. Lett. 7(5), 989–994 (2009)

    Article  CAS  Google Scholar 

  46. Filenko, D., Gotszalk, T., Kazantseva, Z., Rabinovych, O., Koshets, I., Shirshov, Yu., Kalchenko, V., Rangelow, I.W.: Chemical gas sensors based on calixarene-coated discontinuous gold films. Sens. Actuators B 111–112, 264–270 (2005)

    Article  Google Scholar 

  47. Ijeri, V., Vocanson, F., Martelet, C., Jaffrezic-Renault, N.: Capacitive sensing of amino acids using caliraxene-coated silicon transducers. Electroanalysis 19(4), 510–514 (2007)

    Article  CAS  Google Scholar 

  48. Nikolelis, D.P., Raftopoulou, G., Psaroudakis, N., Nikoleli, G.P.: Development of an electrochemical biosensor for the rapid detection of carbofuran based on air stable lipid films with incorporated calix[4]arene phosphoryl receptor. Electroanalysis 20(14), 1574–1580 (2008)

    Article  CAS  Google Scholar 

  49. Hassen, W.M., Martelet, C., Davis, F., Higson, S.P.J., Abdelghani, A., Helali, S., Jaffrezic-Renault, N.: Calix[4]arene based molecules for amino-acid detection. Sens. Actuators B 124(1), 38–45 (2007)

    Article  CAS  Google Scholar 

  50. Mokhtari, B., Pourabdollah, K.: Voltammetric study of nano-baskets of calix[4]-1,3-crowns-5, crowns-6 complexes. Electrochim. Acta 76, 363–367 (2012).

    Google Scholar 

  51. Mokhtari, B., Pourabdollah, K.: Nano-baskets in emulsion liquid membranes for selective extraction of alkali metals. J. Chinese Chem. Soc. (2012). doi:10.1002/jccs.201100737

  52. Mokhtari, B., Pourabdollah, K.: Preparation and characterization of bonded-phases of nano-baskets bearing sulfonyl-carboxamide. J. Liq. Chromatogr. Relat. Tech. (2012). doi:10.1080/10826076.2011.643524

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Acknowledgments

This work was supported by Islamic Azad University (Shahreza branch) and Iran Nanotechnology Initiative Council.

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Correspondence to Kobra Pourabdollah.

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Mokhtari, B., Pourabdollah, K. Electrochemical investigation of nano-baskets of calix[4]-1,3-crowns-5,6 complexes . J Incl Phenom Macrocycl Chem 76, 385–390 (2013). https://doi.org/10.1007/s10847-012-0210-0

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  • DOI: https://doi.org/10.1007/s10847-012-0210-0

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