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Calixarene-engineered surfaces and separation science

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Abstract

After their discovery, calixarenes have attracted the attention of many researchers from various disciplines. This group of supramolecules has an increasing popularity and this is most probably related with the flexibility of calixarene chemistry. Owing to their multifunctional character and stability, calixarenes became important precursors in separation science to derive new-type of sorbents or stationary phases. Immobilization of calixarenes to a suitable solid support (e.g. silica, synthetic polymers, magnetite nanoparticles, etc.) is a very popular concept being used for this purpose, and various immobilization methodologies have been proposed in the literature. In the present work, some state-of-the-art researches and developments published in the past are reviewed in a collective manner, and thus fundamentals of calixarene-immobilization and the application of the obtained materials in sorption and high performance liquid chromatography are represented.

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References

  1. Baeyer, A. Berlin, 5, 25 (1872)

  2. Baekeland, L.H.: Method of making insoluble products of phenol and formaldehyde. US Patent Number(s) 942, 699 (1908)

  3. Zinke, A., Ziegler, E.: Zur Kenntnis des Hartungs-prozesses von Phenol-Formaldehyd-Harzen, X. Mitteilung. Ber. Dtsch. Chem. Ges. 77(B), 264–272 (1944)

    Article  Google Scholar 

  4. Zinke, A., Kretz, R., Leggewie, E., Hössinger, K.: Zur Kenntnis des Härtungsprozesses von Phenol-Formaldehyd-Harzen. Monatsh. Chem. 83, 1213–1227 (1952)

    Article  CAS  Google Scholar 

  5. Gutsche, C.D., Dhawan, B., No, K.H., Muthukrishnan, R.: Calixarenes. 4. The synthesis, characterization, and properties of the calixarenes from para-tert-butylphenol. J. Am. Chem. Soc. 103(13), 3782–3792 (1981)

    Article  CAS  Google Scholar 

  6. Shinkai, S.: Calixarenes–the third generation of supramolecules. Tetrahedron 49(40), 8933–8968 (1993)

    Article  CAS  Google Scholar 

  7. Gutsche, C.D., Nam, K.C.: Calixarenes 22. Synthesis, properties, and metal complexation of aminocalixarenes. J. Am. Chem. Soc. 110(18), 6153–6162 (1988)

    Article  CAS  Google Scholar 

  8. Bayrakcı, M., Ertul, Ş., Yilmaz, M.: Synthesis of di-substituted calix [4] arene-based receptors for extraction of chromate and arsenate anions. Tetrahedron 65(38), 7963–7968 (2009)

    Article  Google Scholar 

  9. Bayrakci, M., Ertul, S., Sahin, O., Yilmaz, M.: Synthesis of two new p-tert-butylcalix[4]arene beta-ketoimin derivatives for extraction of dichromate anion. J. Incl. Phenom. Macro. 63(3–4), 241–247 (2009)

    Article  CAS  Google Scholar 

  10. Bayrakci, M., Ertul, Ş., Yilmaz, M.: Synthesis of new water-soluble phosphonate calixazacrowns and their use as drug solubilizing agents. J. Incl. Phenom. Macro 74(1-4), 293–303 (2012)

    Article  CAS  Google Scholar 

  11. Baldini, L., Sansone, F., Casnati, A., Ungaro, R.: Calixarenes in molecular recognition. In: Supramolecular Chemistry: From Molecules to Nanomaterials. In: Steed, J.W., Gale, P.A., (eds.) pp. 863–878. Wiley, New York (2012). pp. 863–878. ISBN: 978-0-470-74640-0.

  12. Sokoließ, T., Menyes, U., Roth, U., Jira, T.: New calixarene-bonded stationary phases in high-performance liquid chromatography: comparative studies on the retention behavior and on influences of the eluent. J. Chromatogr. A 898, 35–52 (2000)

    Article  Google Scholar 

  13. Glennon, J.D., O’Connor, K., Srijaranai, S., Manley, K., Harris, S.J., McKervey, M.A.: Enhanced chromatographic selectivity for Na+ ions on a calixarene-bonded silica phase. Anal. Lett. 26, 153–162 (1993)

    Article  CAS  Google Scholar 

  14. Friebe, S., Gebauer, S., Krauss, G.J., Goermar, G., Krueger, J.: HPLC on calixarene bonded silica gels. I. Characterization and applications of the p-tert-butyl-calix[4]arene bonded material. J. Chromatogr. Sci. 33(6), 281–284 (1995)

    Article  CAS  Google Scholar 

  15. Brindle, R., Albert, K., Harris, S.J., Troltzsch, C., Horne, E., Glennon, J.D.: Silica-bonded calixarenes in chromatography.1. Synthesis and characterization by solid-state NMR spectroscopy. J. Chromatogr. A 731(1–2), 41–46 (1996)

    Article  CAS  Google Scholar 

  16. Glennon, J.D., Homrne, E., Hall, K., Cocker, D., Kuhn, A., Harris, S.J., McKervey, M.A.: Silica-bonded calixarenes in chromatography.2. Chromatographic retention of metal ions and amino acid ester hydrochlorides. J. Chromatogr. A 731(1–2), 47–55 (1996)

    Article  CAS  Google Scholar 

  17. Lin, L., Wu, C.Y., Yan, Z.Q., Yan, X.Q., Su, X.L., Han, H.M.: Calix[4]arene derivatives as stationary phases for capillary gas chromatography. Chromatographia 47(11–12), 689–694 (1998)

    Article  CAS  Google Scholar 

  18. Ludwig, R.: Calixarenes in analytical and separation chemistry. Fresen. J. Anal. Chem. 367(2), 103–128 (2000)

    Article  CAS  Google Scholar 

  19. Meyer, R., Jira, T.: Calixarene HPLC phases—applications. Curr. Anal. Chem. 3(2), 161–170 (2007)

    Article  CAS  Google Scholar 

  20. Śliwka-Kaszyńska, M.: Calixarenes as stationary phases in high performance liquid chromatography. Crit. Rev. Anal. Chem. 37(3), 211–224 (2007)

    Article  Google Scholar 

  21. 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 

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

    Article  CAS  Google Scholar 

  23. Yang, Y.-B., Harrison, K., Kindsvater, J.: Characterization of a novel stationary phase derived from a hydrophilic polystyrene-based resin for protein cation-exchange high-performance liquid chromatography. J. Chromatogr. A 723(1), 1–10 (1996)

    Article  CAS  Google Scholar 

  24. Perçin, I., Khalaf, R., Brand, B., Morbidelli, M., Gezici, O.: Strong cation-exchange chromatography of proteins on a sulfoalkylated monolithic cryogel. J. Chromatogr. A 1386, 13–21 (2015)

    Article  Google Scholar 

  25. Arena, G., Contino, A., Longo, E., Sciotto, D., Spoto, G., Torrisi, A.: Two calix-crown based stationary phases. Synthesis, chromatographic performance and x-ray photoelectron spectroscopy investigation. J. Supramol. Chem. 2(6), 521–531 (2002)

    Article  CAS  Google Scholar 

  26. Lee, Y.K., Ryu, Y.K., Ryu, J.W., Kim, B.E., Park, J.H.: Reversed-phase liquid chromatography of some positional isomers on calix[6]arene-p-sulfonate-bonded silica. Chromatographia 46(9–10), 507–510 (1997)

    Article  CAS  Google Scholar 

  27. Xiao, X.-Z., Feng, Y.-Q., Da, S.-L., Zhang, Y.: Preparation and evaluation of p-tert-butyl-calix[4]arene bonded silica stationary phases for high performance liquid chromatography. Chromatographia 49(11–12), 643–648 (1999)

    Article  CAS  Google Scholar 

  28. Mollard, A., Ibragimova, D., Antipin, I.S., Konovalov, A.I., Stoikov, I., Zharov, I.: Molecular transport in thiacalix[4]arene-modified nanoporous colloidal films. Microporous Mesoporous Mater. 131(1–3), 378–384 (2010)

    Article  CAS  Google Scholar 

  29. Ozcan, F., Ersoz, M., Yilmaz, M.: Preparation and application of calix[4]arene-grafted magnetite nanoparticles for removal of dichromate anions. Mater. Sci. Eng. C 29(8), 2378–2383 (2009)

    Article  CAS  Google Scholar 

  30. Deng, Z., Liu, J., Hu, C., Yang, L., Du, H., Hu, K., Huang, Y., Yang, X., Jiang, Q., Zhang, S.: Liquid chromatographic behavior of two alanine-substituted calix[4]arene-bonded silica gel stationary phases. J. Sep. Sci. 37(22), 3268–3275 (2014)

    Article  CAS  Google Scholar 

  31. Akoz, E., Erdemir, S., Yilmaz, M.: Immobilization of novel the semicarbazone derivatives of calix[4]arene onto magnetite nanoparticles for removal of Cr(VI) ion. J. Incl. Phenom. Macro. 73(1–4), 449–458 (2012)

    Article  CAS  Google Scholar 

  32. Gezici, O., Tabakci, M., Kara, H., Yilmaz, M.: Synthesis of p-tert-butylcalix[4]arene dinitrile bonded aminopropyl silica and investigating its usability as a stationary phase in HPLC. J. Macromol. Sci. Pure A 43(2), 221–231 (2006)

    Article  CAS  Google Scholar 

  33. Huai, Q.Y., Zhao, B., Zuo, Y.M.: Preparation and evaluation of an end-capped p-tert-butyl-calix[4]arenebonded-silica stationary phase for reversed-phase high-performance liquid chromatography. Chromatographia 59(9–10), 637–645 (2004)

    CAS  Google Scholar 

  34. Xiao, Y.-X., Xiao, X.-Z., Feng, Y.-Q., Wang, Z.-H., Da, S.-L.: High-performance liquid chromatography of sulfonamides and quinolones on p-tert-butyl-calix[6]arene-bonded silica gel stationary phase. Talanta 56(6), 1141–1151 (2002)

    Article  CAS  Google Scholar 

  35. Tabakci, M.: Immobilization of calix[6]arene bearing carboxylic acid and amide groups on aminopropyl silica gel and its sorption properties for Cr(VI). J. Incl. Phenom. Macro. 61(1–2), 53–60 (2008)

    Article  CAS  Google Scholar 

  36. Razavi, N., Akhlaghinia, B.: Cu(II) immobilized on aminated epichlorohydrin activated silica (CAES): as a new, green and efficient nanocatalyst for preparation of 5-substituted-1H-tetrazoles. RSC Adv. 5(16), 12372–12381 (2015)

    Article  CAS  Google Scholar 

  37. Santodonato, J., Lande, S.S., Howard, P.H., Orzel, D., Bogy, D.: Investigation of selected potential environmental contaminants: Epichlorohydrin and epibromohydrin. U.S. Environmental Protection Agency, EPA-560/11-80-006 (1980)

  38. Larson, R.A., Weber, E.J.: Reaction mechanisms in environmental organic chemistry, p. 122. CRC Press, Boca Raton (1994)

    Google Scholar 

  39. Xu, W., Li, J.-S., Feng, Y.-Q., Da, S.-L., Chen, Y.-Y., Xiao, X.-Z.: Preparation and characterization of p-tert-butyl-calix[6]arene bonded silica gel stationary phase for high-performance liquid chromatography. Chromatographia 48(3–4), 245–250 (1998)

    Article  CAS  Google Scholar 

  40. Batista-Viera, F., Janson, J.-C., Carlsson, J.: Affinity chromatography. In: Janson, J.-C. (ed.) Protein Purification: Principles, High Resolution Methods, and Applications, vol. 54, 3rd edn, p. 251. Wiley, Hoboken (2012)

    Google Scholar 

  41. Hu, K., Zhao, W., Wen, F., Liu, J., Zhao, X., Xu, Z., Niu, B., Ye, B., Wu, Y., Zhang, S.: Investigation on the preparation and chromatographic behavior of a new para-tert-butylcalix[4]arene-1,2-crown-4 stationary phase for high performance liquid chromatography. Talanta 85(1), 317–324 (2011)

    Article  CAS  Google Scholar 

  42. Li, L.-S., Liu, M., Da, S.-L., Feng, Y.-Q.: High performance liquid chromatography of aromatic carboxylic acids on p-tert-butyl-calix[8]arene-bonded silica gel stationary phase. Talanta 62(3), 643–648 (2004)

    Article  CAS  Google Scholar 

  43. Zeng, L., Luo, K., Gong, Y.: Preparation and characterization of dendritic composite magnetic particles as a novel enzyme immobilization carrier. J. Mol. Catal. B Enzym. 38(1), 24–30 (2006)

    Article  CAS  Google Scholar 

  44. Sayin, S., Ozcan, F., Yilmaz, M.: Synthesis and evaluation of chromate and arsenate anions extraction ability of a N-methylglucamine derivative of calix[4]arene immobilized onto magnetic nanoparticles. J. Hazard. Mater. 178(1–3), 312–319 (2010)

    Article  CAS  Google Scholar 

  45. Sayin, S., Yilmaz, M.: Synthesis of a new calixarene derivative and its immobilization onto magnetic nanoparticle surfaces for excellent extractants toward Cr(VI), As(V), and U(VI). J. Chem. Eng. Data 56(5), 2020–2029 (2011)

    Article  CAS  Google Scholar 

  46. Sayin, S., Ozcan, F., Memon, S., Yilmaz, M.: Synthesis and oxoanions (dichromate/arsenate) sorption study of N-methylglucamine derivative of calix[4]arene immobilized onto poly[(phenyl glycidyl ether)-co-formaldehyde]. J. Incl. Phenom. Macro. 67(3–4), 385–391 (2010)

    Article  CAS  Google Scholar 

  47. Liu, M., Li, L.-S., Da, S.-L., Feng, Y.-Q.: High performance liquid chromatography with cyclodextrin and calixarene macrocycle bonded silica stationary phases for separation of steroids. Talanta 66(2), 479–486 (2005)

    Article  CAS  Google Scholar 

  48. Jain, V.K., Pandya, R.A., Pillai, S.G., Agrawal, Y.K., Shrivastav, P.S.: Application of a chelate forming calix[4]arene-ovanillinthiosemicarbazone resin to the separation, preconcentration and trace determination of Cu(II), Cd(II) and Pb(II) in natural water samples. Microchim. Acta 147(4), 253–264 (2004)

    Article  CAS  Google Scholar 

  49. Bhatti, A.A., Qureshi, I., Memon, N., Memon, S.: Evaluation of perchlorate sorption behavior of calix[4]arene appended resin. J. Incl. Phenom. Macro. 76(1–2), 55–60 (2013)

    Article  CAS  Google Scholar 

  50. Akceylan, E., Yilmaz, M., Bartsch, R.A.: Immobilization of cyclic alkylamine calix[4]arene derivatives on Merrifield resin: evaluation of extraction ability toward dichromate. J. Macromol. Sci. Pure 43(3), 477–486 (2006)

    Article  CAS  Google Scholar 

  51. Solangi, I.B., Bhatti, A.A., Kamboh, M.A., Memon, S., Bhanger, M.I.: Comparative fluoride sorption study of new calix[4]arene-based resins. Desalination 272(1–3), 98–106 (2011)

    Article  CAS  Google Scholar 

  52. de Gaetano, Y., Clarot, I., Regnouf-de-Vains, J.-B.: Cu(I) and Zn(II) chelations on polymer beads modified by attachment of a bipyridyl-calixarene-based chelate. Tetrahedron Lett. 50(42), 5793–5797 (2009)

    Article  Google Scholar 

  53. Lakouraj, M.M., Hasanzadeh, F., Zare, E.N.: Nanogel and super-paramagnetic nanocomposite of thiacalix[4]arene functionalized chitosan: synthesis, characterization and heavy metal sorption. Iran. Polym. J. 23(12), 933–945 (2014)

    Article  CAS  Google Scholar 

  54. Qureshi, I., Memon, S., Yilmaz, M.: Novel Calix[4]arene-based Amberlite XAD-4 Modified Resin for As(III) removal from water. Clean-Soil Air Water 41(3), 258–266 (2013)

    Article  CAS  Google Scholar 

  55. Urban, I., Ratcliffe, N.M., Duffield, J.R., Elder, G.R., Patton, D.: Functionalized paramagnetic nanoparticles for waste water treatment. Chem. Commun. 46(25), 4583–4585 (2010)

    Article  CAS  Google Scholar 

  56. Thompson, A.B., Cope, S.J., Swift, T.D., Notestein, J.M.: Adsorption of n-butanol from dilute aqueous solution with grafted calixarenes. Langmuir 27(19), 11990–11998 (2011)

    Article  CAS  Google Scholar 

  57. Hofer, S., Ronacher, A., Horak, J., Graalfs, H., Lindner, W.: Static and dynamic binding capacities of human immunoglobulin G on polymethacrylate based mixed-modal, thiophilic and hydrophobic cation exchangers. J. Chromatogr. A 1218(49), 8925–8936 (2011)

    Article  CAS  Google Scholar 

  58. Gezici, O., Ayar, A.: Stepwise frontal analysis to derive equilibrium sorption data for copper and aniline on functionalized sporopollenin. Clean-Soil Air Water 37(4–5), 349–354 (2009)

    Article  CAS  Google Scholar 

  59. Bayrakci, M., Gezici, O., Bas, S.Z., Ozmen, M., Maltas, E.: Novel humic acid-bonded magnetite nanoparticles for protein immobilization. Mater. Sci. Eng. C 42, 546–552 (2014)

    Article  CAS  Google Scholar 

  60. Sayin, S., Ozcan, F., Yilmaz, M.: Two novel calixarene functionalized iron oxide magnetite nanoparticles as a platform for magnetic separation in the liquid–liquid/solid–liquid extraction of oxyanions. Mater. Sci. Eng. C 33(4), 2433–2439 (2013)

    Article  CAS  Google Scholar 

  61. Sayin, S., Yilmaz, E., Yilmaz, M.: Improvement of catalytic properties of Candida Rugosa lipase by sol-gel encapsulation in the presence of magnetic calix[4]arene nanoparticles. Org. Biomol. Chem. 9(11), 4021–4024 (2011)

    Article  CAS  Google Scholar 

  62. Lukashova, M.S., Belikov, K.N., Bryleva, EYu., Kharchenko, S.G., Vishnevskii, S.G., Kalchenko, V.I.: Sorption of Eu(III) on Merrifield resin modified with thiacalix[4]arenes. Prot. Met. Phys. Chem. Surf. 50(5), 608–612 (2014)

    Article  CAS  Google Scholar 

  63. Mangia, A., Pochini, A., Ungaro, R., Andreetti, G.D.: 4-tert-butylcalix[8]areme as a stationary phase in gas-solid chromatography. Anal. Lett. 16(13), 1027–1036 (1983)

    Article  CAS  Google Scholar 

  64. Mnuk, P., Feltl, L.: Gas chromatographic study of the inclusion properties of calixarenes I. p-tert.-Butylcalix[4]arene in a micropacked column. J. Chromatogr. A 696(1), 101–112 (1995)

    Article  CAS  Google Scholar 

  65. Mnuk, P., Feltl, L., Schurig, V.: Gas chromatographic study of the inclusion properties of calixarenes II. Selective properties of cyclic tetra- to octamers derived from phenol, and some problems associated with the use of calixarenes in capillary gas chromatography. J. Chromatogr. A 732(1), 63–74 (1996)

    Article  CAS  Google Scholar 

  66. Śliwka-Kaszyńska, M., Jaszczołt, K., Witt, D., Rachoń, J.: High-performance liquid chromatography of di- and trisubstituted aromatic positional isomers on 1,3-alternate 25,27-dipropoxy-26,28-bis-[3-propyloxy]-calix[4]arene-bonded silica gel stationary phase. J. Chromatogr. A 1055(1–2), 21–28 (2004)

    Google Scholar 

  67. Li, L.-S., Liu, M., Da, S.-L., Feng, Y.-Q.: Studies on the chromatographic behavior of nucleosides and bases on p-tert-butyl-calix[8]arene-bonded silica gel stationary phase by HPLC. Talanta 63(2), 433–441 (2004)

    Article  CAS  Google Scholar 

  68. Li, L.-S., Da, S.-L., Feng, Y.-Q., Liu, M.: Study on the chromatographic behavior of water-soluble vitamins on p-tert-butyl-calix[8]arene-bonded silica gel stationary phase by HPLC. Talanta 64(2), 373–379 (2004)

    Article  CAS  Google Scholar 

  69. Chamseddin, C., Jira, T.: Evaluation of the chromatographic performance of conventional, polar-endcapped and calixarene-bonded stationary phases for the separation of water-soluble vitamins. Chromatographia 76(9–10), 449–457 (2013)

    Article  CAS  Google Scholar 

  70. Śliwka-Kaszyńska, M., Gorczyca, G., Ślebioda, M.: Characterization of 1,3-alternate calix[4]arene-silica bonded stationary phases and their comparison to selected commercial columns by using principal component analysis. J. Chromatogr. A 1217(3), 329–336 (2010)

    Article  Google Scholar 

  71. Śliwka-Kaszyńska, M., Ślebioda, M.: Polycyclic aromatic hydrocarbons as test probes to investigate the retention behavior of 1,3-alternatecalix[4]arene silica-bonded stationary phases. J. Sep. Sci. 37, 543–550 (2014)

    Article  Google Scholar 

  72. Sokoließ, T., Menyes, U., Roth, U., Jira, T.: Separation of cis- and trans-isomers of thioxanthene and dibenz[b, e]oxepin derivatives on calixarene- and resorcinarenebonded high-performance liquid chromatography stationary phases. J. Chromatogr. A 948, 309–319 (2002)

    Article  Google Scholar 

  73. Sokoließ, T., Schönherr, J., Menyes, U., Roth, U., Jira, T.: Characterization of calixarene- and resorcinarene-bonded stationary phases I. Hydrophobic interactions. J. Chromatogr. A 1021, 71–82 (2003)

    Article  Google Scholar 

  74. Elhenawee, M., Hashem, H., Ibrahim, A.E.: Comparison between calixarene and conventional HPLC-stationary phases concerning with separation of antihypertensive drugs. J. Liq. Chromatogr. Relat. Technol. 37, 1–25 (2014)

    Article  CAS  Google Scholar 

  75. Machida, Y., Nishi, H., Nakamura, K.: Enantiomer separation of hydrophobic amino compounds by high-performance liquid chromatography using crown ether dynamically coated chiral stationary phase. J. Chromatogr. A 830, 311–320 (1999)

    Article  CAS  Google Scholar 

  76. Hashem, H., Jira, TH.: Retention behaviour of beta-blockers in HPLC using a monolithic column. J. Sep. Sci. 29, 986–994 (2006)

    Article  CAS  Google Scholar 

  77. Li, L.-S., Da, S.-L., Feng, Y.-Q., Liu, M.: Preparation and characterization of a p-tert-butyl-calix[6]-1,4-benzocrown-4-bonded silica gel stationary phase for liquid chromatography. J. Chromatogr. A 1040, 53–61 (2004)

    Article  CAS  Google Scholar 

  78. Gebauer, S., Friebe, S., Gübitz, G., Krauss, G.J.: High performance liquid chromatography on calixarene-bonded silica gels. II. Separations of regio-and stereoisomers on p-tert-butylcalix[n]arene phases. J. Chromatogr. Sci. 36(8), 383–387 (1998)

    Article  CAS  Google Scholar 

  79. Gebauer, S., Friebe, S., Scherer, G., Gübitz, G., Krauss, G.J.: High performance liquid chromatography on calixarene-bonded silica gels. III. Separations of cis/trans isomers of proline-containing peptides. J. Chromatogr. Sci. 36(8), 388–394 (1998)

    Article  CAS  Google Scholar 

  80. Akceylan, E., Bahadir, M., Yilmaz, M.: Removal efficiency of a calix[4]arene-based polymer for water-soluble carcinogenic direct azo dyes and aromatic amines. J. Hazard. Mater. 162(2–3), 960–966 (2009)

    Article  CAS  Google Scholar 

  81. Stoikov, I.I., Vavilova, A.A., Badaeva, R.D., Gorbachuk, V.V., Evtugyn, V.G., Sitdikov, R.R., Yakimova, L.S., Zharov, I.: Synthesis of hybrid nano- and microsized particles on the base of colloid silica and thiacalix[4]arene derivatives. J. Nanopart. Res. 15(5), 1617 (2013)

    Article  Google Scholar 

  82. Gorbachuk, V.V., Yakimova, L.S., Vavilova, A.A., Ziatdinova, R.V., Rizvanov, IKh, Trifonov, A.A., Samohina, A.I., Evtugyn, V.G., Stoikov, I.I.: MALDI-TOF MS and morphology studies of thiacalixarene-silsesquioxane products of oligo- and polycondensation. Silicon 6, 215–226 (2014)

    Article  CAS  Google Scholar 

  83. Adhikari, B.B., Kanemitsu, M., Kawakita, H.: Jumina, Ohto, K.: Synthesis and application of a highly efficient polyvinylcalix[4]arene tetraacetic acid resin for adsorptive removal of lead from aqueous solutions. Chem. Eng. J. 172(1), 341–353 (2011)

    Article  CAS  Google Scholar 

  84. Adhikari, B.B., Gurung, M., Kawakita, H., Ohto, K.: Solid phase extraction, preconcentration and separation of indium with methylene crosslinked calix[4]- and calix[6]arene carboxylic acid resins. Chem. Eng. Sci. 78, 144–154 (2012)

    Article  CAS  Google Scholar 

  85. Bayrakci, M., Özcan, F., Ertul, Ş.: Synthesis of calixamide nanofibers by electrospinning and toxic anion binding to the fiber structures. Tetrahedron (2015). doi:10.1016/j.tet.2015.03.090

    Google Scholar 

  86. Kim, H.J., Lee, M.H., Mutihac, L., Vicens, J., Kim, J.S.: Host–guest sensing by calixarenes on the surfaces. Chem. Soc. Rev. 41(3), 1173–1190 (2012)

    Article  CAS  Google Scholar 

  87. Erdemir, S., Bahadir, M., Yilmaz, M.: Extraction of carcinogenic aromatic amines from aqueous solution using calix[n]arene derivatives as carrier. J. Hazard. Mater. 168(2–3), 1170–1176 (2009)

    Article  CAS  Google Scholar 

  88. Yilmaz, M., Erdemir, S.: Calixarene-based receptors for molecular recognition. Turk. J. Chem. 37, 558–585 (2013)

    Article  CAS  Google Scholar 

  89. Memon, S., Tabakci, M., Roundhill, D.M., Yilmaz, M.: Synthesis and evaluation of the Cr(VI) extraction ability of amino/nitrile calix[4]arenes immobilized onto a polymeric backbone. React. Funct. Polym. 66(11), 1342–1349 (2006)

    Article  CAS  Google Scholar 

  90. Notestein, J.M., Katz, A., Iglesia, E.: Energetics of small molecule and water complexation in hydrophobic calixarene cavities. Langmuir 22(9), 4004–4014 (2006)

    Article  CAS  Google Scholar 

  91. Schneider, C., Jira, T.: Selectivity of calixarene-bonded silica phases in HPLC: description of special characteristics with a multiple term linear equation at different methanol concentrations. J. Sep. Sci. 33(19), 2943–2955 (2010)

    Article  CAS  Google Scholar 

  92. Śliwka-Kaszyńska, M., Łępicka, K., Ślebioda, M.: Chromatographic behavior of a new hybrid type RP material containing silica bonded 1,3- alternate 25,27-bis-[cyanopropyloxy]-26,28- bis-[3-propyloxy]-calix[4]arene. J. Sep. Sci 33(19), 2956–2964 (2010)

    Article  Google Scholar 

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Acknowledgments

Authors wish to thank Nigde University (Nigde, Turkey) and Karamanoglu Mehmetbey University (Karaman, Turkey) for the facilities provided.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science and Arts, Nigde University, 51240, Nigde, Turkey

    Orhan Gezici

  2. Department of Bioengineering, Faculty of Engineering, Karamanoğlu Mehmetbey University, 70200, Karaman, Turkey

    Mevlüt Bayrakci

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Gezici, O., Bayrakci, M. Calixarene-engineered surfaces and separation science. J Incl Phenom Macrocycl Chem 83, 1–18 (2015). https://doi.org/10.1007/s10847-015-0553-4

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