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Application of crown ethers as stationary phase in the chromatographic methods

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Abstract

Recently, much attention has been paid to chromatographic characteristics and applications of crown ethers. These compounds were employed as chiral stationary phase for resolution of various racemic compounds in high performance chromatography and capillary electrochromatography techniques. Crown ethers also used in gas chromatography as the stationary phase. Recently, it has been found that, crown ethers also may be useful in cation chromatographic separation in ion chromatography for the determination of alkali and alkaline-earth cations, ammonium, and amines. In this paper we have an overview on these applications of crown ethers.

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References

  1. Pedersen, C.J.: Cyclic polyethers and their complexes with metal salts. J. Am. Chem. Soc. 89, 7017–7036 (1967)

    Article  CAS  Google Scholar 

  2. Rounaghi, G.H., Mohammad Zade Kakhki, R.: Thermodynamic study of complex formation between dibenzo-18-crown-6 and UO2 2+ cation in different non-aqueous binary solutions. J. Incl. Phenom. Macrocycl. Chem. 63, 117–122 (2009)

    Article  CAS  Google Scholar 

  3. Rounaghi, G.H., Zavar, M.H., Mohammad Zade Kakhki, R.: Thermodynamic behaviour of complexation process between DB18C6 with K+, Ag+, NH4+ and Hg2+ cations in ethylacetate-dimethylformamide binary media. Russ J Coord Chem 34, 167–171 (2008)

    Article  CAS  Google Scholar 

  4. Rounaghi, G.H., Mohajeri, M., Soruri, F., Mohamadzadeh Kakhki, R.: Solvent influence upon complex formation between dibenzo-18-crown-6 with the Y3+ metal cation in pure and binary mixed organic solvents. J. Chem. Eng. Data 56, 2836–2840 (2011)

    Article  CAS  Google Scholar 

  5. Razghandi, F., Rounaghi, Gh., Mohammadzadeh Kakhki, R.: Complexation study of dibenzo-18-crown-6 with UO2 2+ cation in binary mixed non-aqueous solutions. J. Incl. Phenom. Macrocycl. Chem. (2011). doi:10.1007/s10847-011-0053-0

  6. Rounaghi, G.H., Mohajeri, M., Atashi, Z., Mohamadzadeh kakhki, R.: Conductometric study of complexation reaction between 15-crown-5 and Cr3+, Mn2+ and Zn2+ metal cations in pure and binary mixed organic solvents. J. Incl. Phenom. Macrocycl. Chem. (2011). doi:10.1007/s10847-011-0081-9

  7. Mohammad Zadeh Kakhki, R., Rounaghi, G.H.: Competitive bulk liquid membrane transport of heavy metal cations using the 18-crown-6 ligand as an ionophore. J. Chem. Eng. Data 56, 3169–3174 (2011)

    Article  CAS  Google Scholar 

  8. Mohapatra, P.K., Lakshmi, D.S., Bhattacharyya, A., Manchanda, V.K.: Evaluation of polymer inclusion membranes containing crown ethers for selective cesium separation from nuclear waste solution. J. Hazard. Mater. 169, 472–479 (2009)

    Article  CAS  Google Scholar 

  9. Shamsipur, M., Davarkhah, R., Khanchi, A.R.: Facilitated transport of uranium(VI) across a bulk liquid membrane containing thenoyltrifluoroacetone in the presence of crown ethers as synergistic agents. Sep. Purif. Technol. 71, 63–69 (2010)

    Article  CAS  Google Scholar 

  10. Pirkle, W.H., Pochapsky, T.C.: Considerations of chiral recognition relevant to the liquid chromatographic separation of enantiomers. Chem. Rev. 89, 347–362 (1989)

    Article  CAS  Google Scholar 

  11. Berthod, A., Chang, S.C., Armstrong, D.W.: Empirical procedure that uses molecular structure to predict enantioselectivity of chiral stationary phases. Anal. Chem. 64, 395–404 (1992)

    Article  CAS  Google Scholar 

  12. Allenmark, S.G.: Chromatographic Enantioseparations: Methods and Applications. Ellis Horwood, New York (1993)

    Google Scholar 

  13. Subramanian, G.: A Practical Approach to Chiral Separations by Liquid Chromatography. VHC, Weinheim (1994)

    Google Scholar 

  14. Zief, M., Crane, L.J.: Chromatographic Chiral Separations. Marcel Dekker, New York (1998)

    Google Scholar 

  15. Sogah, G.D.Y., Cram, D.J.: Chromatographic optical resolution through chiral complexation of amino ester salts by a host covalently bound to silica gel. J. Am. Chem. Soc. 97, 1259–1261 (1975)

    Article  Google Scholar 

  16. Shinbo, T., Yamaguchi, T., Nishimura, K., Sugiura, M.: Chromatographic separation of racemic amino acids by use of chiral crown ether-coated reversed-phase packings. J. Chromatogr. A 405, 145–153 (1987)

    Article  CAS  Google Scholar 

  17. Shinbo, T., Yamaguchi, T., Yanagishita, H., Kitamoto, D., Sakaki, K., Sugiura, M.: Improved crown ether-based chiral stationary phase. J. Chromatogr. A 625, 101–108 (1992)

    Article  CAS  Google Scholar 

  18. Lee, W., Hong, C.Y.: Direct liquid chromatographic enantiomer separation of new fluoroquinolones including gemifloxacin. J. Chromatogr. A 879, 113–120 (2000)

    Article  CAS  Google Scholar 

  19. Machida, Y., Nishi, H., Nakamura, K., Nakai, H., Sato, T.: Enantiomer separation of amino compounds by a novel chiral stationary phase derived from crown ether. J. Chromatogr. A 805, 85–92 (1998)

    Article  CAS  Google Scholar 

  20. Hyun, M.H., Jin, J.S., Lee, W.: A new hplc chiral stationary phase for the direct resolution of racemic quinolone antibacterials containing a primary amino group. Bull. Korean Chem. Soc. 19, 819–821 (1998)

    CAS  Google Scholar 

  21. Hyun, M.H., Jin, J.S., Lee, W.: Liquid chromatographic resolution of racemic amino acids and their derivatives on a new chiral stationary phase based on crown ether. J. Chromatogr. A 822, 155–161 (1998)

    Article  Google Scholar 

  22. Hyun, M.H., Jin, J.S., Koo, H.J., Lee, W.: Liquid chromatographic resolution of racemic amines and amino alcohols on a chiral stationary phase derived from crown ether. J. Chromatogr. A 837, 75–82 (1999)

    Article  CAS  Google Scholar 

  23. Hyun, M.H., Han, S.C., Lipshutz, B.H., Shin, Y.J., Welch, C.: Liquid chromatographic resolution of racemic amines, amino alcohols and related compounds on a chiral crown ether stationary phase. J. Chromatogr. A 959, 75–83 (2002)

    Article  CAS  Google Scholar 

  24. Kontos, Z., Huszthy, P., Bradshaw, J.S., Izatt, R.M.: Enantioseparation of racemic organic ammonium perchlorates by a silica gel bound optically active di-tert-butylpyridino-18-crown-6 ligand. Tetrahedr. Asymmetry 10, 2087–2099 (1999)

    Article  CAS  Google Scholar 

  25. Hirose, K., Nakamura, T., Nishioka, R., Ueshige, T., Tobe, Y.: Preparation and evaluation of novel chiral stationary phases covalently bound with chiral pseudo-18-crown-6 ethers. Tetrahedron Lett. 44, 1549–1551 (2003)

    Article  CAS  Google Scholar 

  26. Hirose, K., Yongzhu, J., Nakamura, T., Nishioka, R., Ueshige, T., Tobe, Y.: Chiral stationary phase covalently bound with a chiral pseudo-18-crown-6 ether for enantiomer separation of amino compounds using a normal mobile phase. Chirality 17, 142–148 (2005)

    Article  CAS  Google Scholar 

  27. Hirose, K., Yongzhu, J., Nakamura, T., Nishioka, R., Ueshige, T., Tobe, Y.: Preparation and evaluation of a chiral stationary phase covalently bound with chiral pseudo-1 8-crown-6 ether having 1-phenyl-1,2-cyclohexanediol as a chiral unit. J. Chromatogr. A 1078, 35–41 (2005)

    Article  CAS  Google Scholar 

  28. Hyun, M.H., Min, H.J., Cho, Y.: Resolution of tocainide and its analogues on liquid chromatographic chiral stationary phases based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid. J. Bull. Korean Chem. Soc. 24, 911–915 (2003)

    Article  CAS  Google Scholar 

  29. Hyun, M.H., Han, S.C., Jin, J.S., Lee, W.: Separation of the stereoisomers of racemic fluoroquinolone antibacterial agents on a crown-ether-based chiral HPLC stationary phase. Chromatographia 52, 473–476 (2000)

    Article  CAS  Google Scholar 

  30. Hyun, M.H., Han, S.C., Cho, Y.J., Jin, J.S., Lee, W.: Liquid chromatographic resolution of gemifloxacin mesylate on a chiral stationary phase derived from crown ether. Biomed. Chromatogr. 16, 356–360 (2002)

    Article  CAS  Google Scholar 

  31. Hyun, M.H., Kim, Y.H., Cho, Y.J.: Bull. Korean Chem. Soc. 25, 400–402 (2004)

    Article  CAS  Google Scholar 

  32. Hyun, M.H., Cho, Y.J.: Preparation and application of a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid without extra free aminopropyl groups on silica surface. J. Sep. Sci. 28, 31–38 (2005)

    Article  CAS  Google Scholar 

  33. Hyun, M.H., Jin, J.S., Han, SCh., Cho, Y.J.: The effect of analyte lipophilicity on the resolution of α-amino acids on a HPLC chiral stationary phase based on crown ether. Microchem. J. 70, 205–209 (2001)

    Article  CAS  Google Scholar 

  34. Jin, J.S., Stalcup, A.M., Hyun, M.H.: Impact of triethylamine as a mobile phase additive on the resolution of racemic amino acids on an (1)-18-crown-6-tetracarboxylic acid-derived chiral stationary phase. J. Chromatogr. A 933, 83–90 (2001)

    Article  CAS  Google Scholar 

  35. Hyun, M.H., Tan, G., Ying Xue, J.: Unusual resolution of N-(3,5-dinitrobenzoyl)-α-amino acids on a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid. J. Chromatogr. A 1097, 188–191 (2005)

    Article  CAS  Google Scholar 

  36. Berkecz, R., Sztojkov-Ivanov, A., Ilisz, I., Forro, E., Fulop, F., Hyun, M.H., Peter, A.: High-performance liquid chromatographic enantioseparation of β-amino acid stereoisomers on a (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase. J. Chromatogr. A1125, 138–143 (2006)

    Google Scholar 

  37. Juaristi, E., Soloshonok, V.A.: Enantioselective Synthesis of α-Amino Acids, 2nd edn. Wiley, New York (2005)

    Book  Google Scholar 

  38. Hyun, M.H., Choi, H.J., Kang, B.S., Tan, G., Cho, Y.J.: Resolution of β-amino acids on a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid without extra free aminopropyl groups on silica surface: The effect of ammonium ion mobile phase modifier on the resolution behaviors. Bull. Korean Chem. Soc. 27, 1775–1779 (2006)

    Article  CAS  Google Scholar 

  39. Machida, Y., Nishi, H., Nakamura, K.: Separation of the enantiomers of amino and amide compounds on novel chiral stationary phases derived from a crown ether. Chromatographia 49, 621–627 (1999)

    Article  CAS  Google Scholar 

  40. Steffeck, R.J., Zelechonok, Y., Gahm, K.H.: Enantioselective separation of racemic secondary amines on a chiral crown ether-based liquid chromatography stationary phase. J. Chromatogr. A 947, 301–305 (2002)

    Article  CAS  Google Scholar 

  41. Hyun, M.H., Han, S.C., Lipshutz, B.H., Shin, Y.-J., Welch, C.J.: New chiral crown ether stationary phase for the liquid chromatographic resolution of α-amino acid enantiomers. J. Chromatogr. A 910, 359–365 (2001)

    Article  CAS  Google Scholar 

  42. Myung, H.H., Han, SCh.: Liquid chromatographic separation of the enantiomers of fluoroquinolone antibacterials on a chiral stationary phase based on a chiral crown ether. J. Biochem. Biophys. Methods 54, 235–243 (2002)

    Article  Google Scholar 

  43. Hyun, M.H., Han, SCh., Bruce, L., Shin, H., Christopher, Y.-J., Welch, J.: Liquid chromatographic resolution of racemic amines, amino alcohols and related compounds on a chiral crown ether stationary phase. J. Chromatogr. A 959, 75–83 (2002)

    Article  CAS  Google Scholar 

  44. Hyun, M.H., Min, H.J., Cho, Y.J.: Enantiomeric separation of tocainide and its analogues on an optically active crown ether-based stationary phase by liquid chromatography. J. Chromatogr. A 996, 233–237 (2003)

    Article  CAS  Google Scholar 

  45. Pirkle, W.H., Readnour, R.S.: The influence of end-capping on the enantioselectivity of a chiral phase. Chromatographia 31, 129–132 (1991)

    Article  CAS  Google Scholar 

  46. Hyun, M.H., Kim, D.H.: Spacer length effect of a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid. Chirality 16, 294–301 (2004)

    Article  CAS  Google Scholar 

  47. Hyun, M.H., Song, Y., Cho, Y.J., Kim, D.H.: Preparation of a new doubly tethered chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid and its application. J. Chromatogr. A 1108, 208–217 (2006)

    Article  CAS  Google Scholar 

  48. Hyun, M.H., Han, SCh., Choi, H.J., Kang, B.S., Hyun, J.H.: Effect of the residual silanol group protection on the liquid chromatographic resolution of racemic primary amino compounds on a chiral stationary phase based on optically active (3,3′-diphenyl-1,1′-binaphthyl)-20-crown-6. J. Chromatogr. A 1138, 169–174 (2007)

    Article  CAS  Google Scholar 

  49. Naemura, K., Takeuchi, S., Asada, M., Ueno, K., Hirose, K., Tobe, Y., Kaneda, T., Sakata, Y.: Synthesis of azophenolic crown ethers of C s symmetry incorporating cis-1-phenylcyclohexane-1,2-diol residues as a steric barrier and diastereotopic face selectivity in complexation of amines by their diastereotopic faces. J. Chem. Soc. Perkin Trans. 1, 1429–1435 (1995)

    Article  Google Scholar 

  50. Kaneda, T., Hirose, K., Misumi, S.: Chiral azophenolic acerands: color indicators to judge the absolute configuration of chiral amines. J. Am. Chem. Soc. 111, 742–743 (1989)

    Article  CAS  Google Scholar 

  51. Naemura, K., Nishikawa, Y., Fuji, J., Hirose, K., Tobe, Y.: Preparation of homochiral phenolic crown ethers containing para-substituted phenol moiety and chiral subunits derived from (S)-1-phenylethane-1,2-diol: their chiral recognition behaviour in complexation with neutral amines. Tetrahedron Asymmetry 8, 873–882 (1997)

    Article  CAS  Google Scholar 

  52. Naemura, K., Nishioka, K., Ogasahara, K., Nishikawa, Y., Hirose, K., Tobe, Y.: Preparation and temperature-dependent enantioselectivities of homochiral phenolic crown ethers having aryl chiral barriers: thermodynamic parameters for enantioselective complexation with chiral amines. Tetrahedron Asymmetry 9, 563–574 (1998)

    Article  CAS  Google Scholar 

  53. Wang, H., Tian, X., Yang, D., Pan, Y., Wu, Q., He, Ch.: Synthesis and enantiomeric recognition ability of 22-crown-6 ethers derived from rosin acid and BINOL. Tetrahedron Asymmetry 22, 381–386 (2011)

    Article  CAS  Google Scholar 

  54. Hirose, E.K., Yachi, Y., Tobe, Y.: Novel chiral recognition beyond the limitation due to the law of mass action: highly enantioselective chiral sensing based on non-linear response in phase transition. Chem. Commun. 47, 6617–6619 (2011)

    Article  CAS  Google Scholar 

  55. Hirose, K., Fujiwara, A., Matsunaga, K., Aoki, N., Tobe, Y.: Chiral recognition of secondary amines by using chiral crown ether and podand. Tetrahedron Lett. 43, 8539–8542 (2002)

    Article  CAS  Google Scholar 

  56. Hirose, K., Fujiwara, A., Matsunaga, K., Aoki, N., Tobe, Y.: Preparation of phenolic chiral crown ethers and podands and their enantiomer recognition ability toward secondary amines. Tetrahedron Asymmetry 14, 555–566 (2003)

    Article  CAS  Google Scholar 

  57. Yongzhu, J., Hirose, K., Nakamuraa, T., Nishiok, R., Ueshige, T., Tobe, Y.: Preparation and evaluation of a chiral stationary phase covalently bound with a chiral pseudo-18-crown-6 ether having a phenolic hydroxy group for enantiomer separation of amino compounds. J. Chromatogr. A 1129, 201–207 (2006)

    Article  CAS  Google Scholar 

  58. Seyhan, S., Turgut, Y., Merdivan, M., Hos_go ren, H.: Chiral separation of amino acids using a chiral crown ether by impregnation on a polymeric support and monoamine modified silica gel. Tetrahedron Asymmetry 17, 1700–1704 (2006)

    Article  CAS  Google Scholar 

  59. Kartozia, I., D’Orazio, G., Chankvetadze, B., Fanali, S.: Evaluation of cyclodextrins modified with dichloro-, dimethyl-, and chloromethylphenylcarbamate groups as chiral stationary phases for capillary electrochromatography. J. Capill. Electrophor. 9, 31–38 (2005)

    CAS  Google Scholar 

  60. Hyun, M.H., Tan, G., Cho, Y.J.: J. Liq. Chromatogr. Relat. Technol. 27, 1671–1680 (2004)

    Article  CAS  Google Scholar 

  61. Aboul-Enein, H.Y., Serignese, V.: Direct chiral resolution of phenylalkylamines using a crown ether chiral stationary phase. Biomed. Chromatogr. 11, 7–10 (1997)

    Article  CAS  Google Scholar 

  62. Chen, S., Yuan, H., Grinberg, N., Dovletoglou, A., Bicker, G.: J. Liq. Chromatogr. Technol 26, 425–442 (2003)

    Article  CAS  Google Scholar 

  63. Barder, T.J., Wohlman, P.J., Thrall, C., DuBois, P.D.: Fast chromatography and nonporous silica. LC GC 15, 918–926 (1997)

    CAS  Google Scholar 

  64. Verleysen, K., Sandra, P.: Enantiomeric separation of some amino acids and derivatives by capillary electrophoresis with 18-crown-6-tetracarboxylic acid as chiral selector. J. Microcol. Sep. 11, 37–43 (1999)

    Article  CAS  Google Scholar 

  65. Schurig, V., Wistuba, D.: Recent innovations in enantiomer separation by electrochromatography utilizing modified cyclodextrins as stationary phases. Electrophoresis 20, 2313–2328 (1999)

    Article  CAS  Google Scholar 

  66. Park, J.W., Lee, S.Y., Park, K.K.: Molecular recognition of organic ammonium ions by diaza-crown ether-modified β-cyclodextrin in aqueous media. Chem. Lett. 6, 594 (2000)

    Article  Google Scholar 

  67. Willner, I., Goren, Z.: Diaza-crown ether capped cyclodextrin. A receptor with two recognition sites. J. Chem. Soc. Chem. Commun. 23, 1469–1470 (1983)

    Article  Google Scholar 

  68. Gong, Y., Xue, G., Bradshaw, J.S., Lee, M.L., Lee, H.K.: Synthesis of crown ether-capped 3-(2-O-β-cyclodextrin)-2-hydroxypropylsilyl silica particles for use as chiral stationary phases in chromatography. J. Heterocycl. Chem. 38, 1317–1321 (2001)

    Article  CAS  Google Scholar 

  69. Gong, Y., Xue, G., Xiang, Y., Bradshaw, J.S., Lee, M.L., Lee, H.K.: Synthesis of cyclam-capped -cyclodextrin-bonded silica particles for use as chiral stationary phases in capillary electrochromatography. Tetrahedron Lett. 43, 2463–2466 (2002)

    Article  CAS  Google Scholar 

  70. Gong, Y., Lee, H.K.: Enantiomeric separation in capillary electrochromatography by using crown ether-capped beta-cyclodextrin bonded silica particles as chiral stationary phase. Helv. Chim. Acta 85, 3283–3293 (2002)

    Article  CAS  Google Scholar 

  71. Gong, Y., Xiang, Y., Yue, B., Xue, G., Bradshaw, J.S., Lee, H.K., Lee, M.L.: Application of diaza-18-crown-6-capped β-cyclodextrin bonded silica particles as chiral stationary phases for ultrahigh pressure capillary liquid chromatography. J. Chromatogr. A 1002, 63–70 (2003)

    Article  CAS  Google Scholar 

  72. Zeng, Z., Qiu, W., Xing, H., Huang, Z.: Sol-gel-derived crown ether stationary phase for capillary gas chromatography. Anal Sci Capill Gas Chromatogr 16, 851–856 (2000)

    CAS  Google Scholar 

  73. Blomberg, L.G.: Stationary phases for capillary gas chromatography. TrAC Trends Anal. Chem. 6, 41–45 (1987)

    Article  CAS  Google Scholar 

  74. Yong-Hao, J., Ruo-Nong, F., Zai-Fu, H.: Use of crown ethers in gas chromatography. J. Chromatogr. 469, 153–159 (1989)

    Article  Google Scholar 

  75. Fine, D.D., Gearhart, H.L., Mottola, H.A.: Preparation and gas chromatographic characterization of some crown-ether stationary phases. Talanta 32, 751–756 (1985)

    Article  CAS  Google Scholar 

  76. Rouse, C.A., Fintinson, A.C., Tarbet, B.J., Pixton, C., Djordjevie, N.M., Markides, K.E., Bradshaw, J.S., Lee, M.L.: Anal. Chem. 60, 901 (1988)

    Article  CAS  Google Scholar 

  77. Wu, C.-Y., Wang, Ch-M, Zeng, Zh-R, Lu, X.-R.: Anal. Chem. 62, 968–971 (1990)

    Article  CAS  Google Scholar 

  78. Zeng, Z.R., Liu, M.: Chromatographia 48, 817–822 (1998)

    Article  CAS  Google Scholar 

  79. Zeng, Z.-R., Wu, C.-Y., Yan, H., Huang, Z.-F., Wang, Y.-T.: Preparation and characteristics of two new GC stationary phases-dihydroxy crown ether containing polysiloxane. Chromatographia 34, 85–90 (1992)

    Article  Google Scholar 

  80. Zeng, Zh, Qiu, W., Xing, H., Huang, Z.: Sol-gel-derived crown ether stationary phase for capillary gas chromatography. J. Anal. Sci. 16, 851–854 (2000)

    Article  CAS  Google Scholar 

  81. Qing, X., Zhou, Z., Xie, M., Zeng, Y., Tang, Y.: Gas chromatographic characteristics and application studies of the stationary phase of CH-B-15-C-5. Talanta 46, 45–51 (1998)

    Article  CAS  Google Scholar 

  82. Finkelmann, H., et al.: Polynuclear Aromatic Hydrocarbons: Physical and Biological Chemistry, p. 275. Battelle Press, Columbus (1982)

    Google Scholar 

  83. Percec, V., Rodenhouse, R.: Liquid crystal polymers containing macroheterocyclic ligands. 2. Side chain liquid crystal polysiloxanes and polymethacrylates containing 4-(.omega.-alkan-1-yloxy)-4′-(4′-carboxybenzo-15-crown-5)biphenyl side groups. Macromolecules 22, 4408–4412 (1989)

    Article  CAS  Google Scholar 

  84. Fu, R., Jing, P., Gu, J.: Anal. Chem. 65, 2141–2144 (1993)

    Article  CAS  Google Scholar 

  85. Blasius, E., Janzen, K.-P., Adrian, W., Klautke, G., Lorschelder, R., Maurer, PA., Nguyen, V. B., Nguyen-Tlen, T., Schoiten, G., Stockem-er, J.: Fresenius’ J. Anal. Chem. 284, 337–360

  86. Blasius, E., Janzen, K.-P., Klein, W., Klotz, H., Nguyen, V.B., Nguyen-Tien, T., Pfeiffer, R., Scholten, G., Simon, H., Stockemer, H., Tous-saint, A.: Preparation, characterization and application of ion exchangers with cyclic polyether anchor groups. J. Chromatogr. 201, 147–166 (1980)

    Article  CAS  Google Scholar 

  87. Kimura, K., Harino, H., Hayata, E., Shono, T.: Liquid chromatography of alkali and alkaline-earth metal ions using octadecylsilanized silica columns modified in situ with lipophilic crown ethers. Anal. Chem. 58, 22–2233 (1986)

    Article  Google Scholar 

  88. Nakajlma, M., Kimura, K., Shono, T.: Liquid chromatography of alkali and alkaline earth metal salts on poly(benzo-15-crown-5)- and bis(benzo-15-crown-5)-modified silicas. Anal. Chem. 55, 463–467 (1983)

    Article  Google Scholar 

  89. Nakajima, M., Kimura, K., Shono, T.: Ion-chromatographic behavior of silica gels modified by poly- and bis(crown ether)s of benzo-18-crown-6. Bull. Chem. Soc. Japan 56, 3052–3056 (1983)

    Article  CAS  Google Scholar 

  90. NakaJima, M., Kimura, K., Hayata, E., Shono, T.: Ion chromatography on poly(crown ether)-modified silica possessing high affinity for sodium. J. Liq. Chromatogr. 7, 2115–2125 (1984)

    Article  CAS  Google Scholar 

  91. Igawa, M., Saito, K., Tsukamoto, J., Tanaka, M.: Ion chromatographic separation of anions on silica-coated polyamide crown resin. Anal. Chem. 53, 1942–1944 (1981)

    Article  CAS  Google Scholar 

  92. Igawa, M., Salto, K., Tanaka, M., Yamabe, T.: Separation mechanism of anion chromatography on silica gel coated with polyamide crown resin and its application. BunsekiKagaku 32, E137–E141 (1983)

    CAS  Google Scholar 

  93. Kimura, K., Hayata, E., Shono, T.: Convenient, efficient crown ether-containing stationary phases for chromatographic separation of al-kali metal ions: dynamic coating of highly lipophilic crown ethers on octadecylsilanized silica. J. Chem. Soc. Chem. Commun. 271–272 (1984)

  94. Kimura, K., Harino, H., Hayata, E., Shono, T.: Liquid chromatography of alkali and alkaline-earth metal ions using octadecylsilanized silica columns modified in situ with lipophilic crown ethers. Anal. Chem. 58, 2233–2237 (1986)

    Article  CAS  Google Scholar 

  95. Laubli, M.W., Kampus, B.: Selectivity enhancement on a poly(butadiene-maleic acid)-coated cation phase induced by ethylene oxide-based complexing agents. J. Chromatogr. A 706, 103–107 (1995)

    Article  Google Scholar 

  96. Rey, M.A., Pohl, C.A., Jagodzinski, J.J., Kaiser, E.Q., Riviello, J.M.: A new approach to dealing with high-to-low concentration ratios of sodium and ammonium ions in ion chromatography. J. Chromatogr. A 804, 201–209 (1998)

    Article  CAS  Google Scholar 

  97. Saari-Nordhaus, R. Pham, H. Anderson Jr. J.M. Presented at the Pittsburg Conference 1999, paper, p 2292

  98. Saari-Nordhaus, R., Anderson Jr, J.M.: Alternative approach to enhancing cation selectivity in ion chromatography. J. Chromatogr. A 1039, 123–127 (2004)

    Article  CAS  Google Scholar 

  99. Colon, L.A., Guo, Y., Fermier, A.: Capillary electrochromatography. Anal. Chem. 69, 461A–467A (1997)

    Article  CAS  Google Scholar 

  100. Svec, F., Peters, E.C., Sykora, D., Yu, C., Frechet, J.M.J.: Monolithic stationary phases for capillary electrochromatography based on synthetic polymers: designs and applications. J. High Resolut. Chromatogr. 23, 3–18 (2000)

    Article  CAS  Google Scholar 

  101. Fujimoto, C.: Charged polyacrylamide gels for capillary electrochromatographic separations of uncharged, low molecular weight compounds. Anal. Chem. 67, 2050–2053 (1995)

    Article  CAS  Google Scholar 

  102. Fujimoto, C., Fujise, Y., Matsuzawa, E.: Fritless packed columns for capillary electrochromatography: separation of uncharged compounds on hydrophobic hydrogels. Anal. Chem. 68, 2753–2757 (1996)

    Article  CAS  Google Scholar 

  103. Palm, A., Novotny, M.V.: Macroporous polyacrylamide/poly(ethylene glycol) matrixes as stationary phases in capillary electrochromatography. Anal. Chem. 69, 4499–4507 (1997)

    Article  CAS  Google Scholar 

  104. Gusev, I., Huang, X., Horvath, Cs: Capillary columns with in situ formed porous monolithic packing for micro high-performance liquid chromatography and capillary electrochromatography. J. Chromatogr. A 855, 273–290 (1999)

    Article  CAS  Google Scholar 

  105. Peters, E.C., Petro, M., Svec, F., Frechet, J.M.J.: Molded rigid polymer monoliths as separation media for capillary electrochromatography. 1. Fine control of porous properties and surface chemistry. Anal. Chem. 70, 2288–2295 (1998)

    Article  CAS  Google Scholar 

  106. Peters, E.C., Petro, M., Svec, F., Frechet, J.M.J.: Molded rigid polymer monoliths as separation media for capillary electrochromatography. 2. Effect of chromatographic conditions on the separation. Anal. Chem. 70, 2296–2302 (1998)

    Article  CAS  Google Scholar 

  107. Wulff, G.: Molecular imprinting in cross-linked materials with the aid of molecular templates: a way towards artificial antibodies. Angew. Chem. Int. Ed. Engl. 34, 1812–1832 (1995)

    Article  CAS  Google Scholar 

  108. Liao, J.-L., Chen, N., Ericson, C., Hjerten, S.: Preparation of continuous beds derivatized with one-step alkyl and sulfonate groups for capillary electrochromatography. Anal. Chem. 68, 3468–3472 (1996)

    Article  CAS  Google Scholar 

  109. Tanaka, N., Nagayama, H., Kobayashi, H., Ikegami, T., Hosoya, K., Ishizuka, N., Minakuchi, H., Nakanishi, K., Cabrera, K., Lubda, D.: Monolithic silica columns for HPLC, Micro-HPLC, and CEC. J. High Resolut. Chromatogr. 23, 111–116 (2000)

    Article  CAS  Google Scholar 

  110. Li, S., Lloyd, D.K.: Direct chiral separations by capillary electrophoresis using capillaries packed with an alpha.1-acid glycoprotein chiral stationary phase. Anal. Chem. 65, 3684–3690 (1993)

    Article  CAS  Google Scholar 

  111. Wistuba, D., Czesla, H., Roeder, M., Schurig, V.: Enantiomer separation by pressure-supported electrochromatography using capillaries packed with a permethyl-β-cyclodextrin stationary phase. J. Chromatogr. A 815, 183–188 (1998)

    Article  CAS  Google Scholar 

  112. Carter-Finch, A.S., Smith, N.W.: Enantiomeric separations by capillary electrochromatography using a macrocyclic antibiotic chiral stationary phase. J. Chromatogr. A 848, 375–385 (1999)

    Article  CAS  Google Scholar 

  113. Wikstrom, H., Svensson, L.A., Torstensson, A., Owens, P.K.: Immobilisation and evaluation of a vancomycin chiral stationary phase for capillary electrochromatography. J. Chromatogr. A 869, 395–409 (2000)

    Article  CAS  Google Scholar 

  114. Mayer, S., Schurig, V.: Enantiomer separation using mobile and immobile cyclodextrin derivatives with electromigration. Electrophoresis 15, 835 (1994)

    Article  CAS  Google Scholar 

  115. Mayer, S., Schleimer, M., Schurig, V.: Dual chiral recognition system involving cyclodextrin derivatives in capillary electrophoresis. J. Microcol. Sep. 6, 43–48 (1994)

    Article  CAS  Google Scholar 

  116. Armstrong, D.W., Tang, Y., Ward, T., Nichols, M.: Derivatized cyclodextrins immobilized on fused-silica capillaries for enantiomeric separations via capillary electrophoresis, gas chromatography, or supercritical fluid chromatography. Anal. Chem. 65, 1114–1117 (1993)

    Article  CAS  Google Scholar 

  117. Schweitz, L., Andersson, L.I., Nilsson, S.: Capillary electrochromatography with predetermined selectivity obtained through molecular imprinting. Anal. Chem. 69, 1179–1183 (1997)

    Article  CAS  Google Scholar 

  118. Peters, E.C., Lewandowski, K., Petro, M., Svec, F., Frechet, J.M.J.: Chiral electrochromatography with a “molded” rigid monolithic capillary column. Anal. Commun. 35, 83–86 (1998)

    Article  CAS  Google Scholar 

  119. Lämmerhofer, M., Peters, E.C., Yu, C., Svec, F., Fréchet, J.M.J., Lindner, W.: Chiral monolithic columns for enantioselective capillary electrochromatography prepared by in situ copolymerization of a monomer with quinidine functionality: 1. Optimization of polymerization conditions, porous properties, and chemistry of the stationary phase. Anal. Chem. 72, 4614–4622 (2000)

    Article  CAS  Google Scholar 

  120. Lämmerhofer, M., Svec, F., Fréchet, J.M.J., Lindner, W.: Chiral monolithic columns for enantioselective capillary electrochromatography prepared by copolymerization of a monomer with quinidine functionality: 2. Effect of chromatographic conditions on the chiral separations. Anal. Chem. 72, 4623–4628 (2000)

    Article  CAS  Google Scholar 

  121. Koide, T., Ueno, K.: Enantiomeric separations of cationic and neutral compounds by capillary electrochromatography with charged polyacrylamide gels incorporating chiral selectors. Anal. Sci. 14, 1021–1023 (1998)

    Article  CAS  Google Scholar 

  122. Koide, T., Ueno, K.: Enantiomeric separations of cationic and neutral compounds by capillary electrochromatography with β-cyclodextrin-bonded charged polyacrylamide gels. Anal. Sci. 15, 791–794 (1999)

    Article  CAS  Google Scholar 

  123. Koide, T., Ueno, K.: Enantiomeric separations of cationic and neutral compounds by capillary electrochromatography with monolithic chiral stationary phases of beta-cyclodextrin-bonded negatively charged polyacrylamide gels. J. Chromatogr. A 893, 177–187 (2000)

    Article  CAS  Google Scholar 

  124. Koide, T., Ueno, K.: Enantiomeric separations by capillary electrochromatography with charged polyacrylamide gels incorporating chiral selectors. Anal. Sci. 16, 1065–1070 (2000)

    Article  CAS  Google Scholar 

  125. Guttman, A., Paulus, A., Cohen, A.S., Grinberg, N., Karger, B.L.: Use of complexing agents for selective separation in high-performance capillary electrophoresis: chiral resolution via cyclodextrins incorporated within polyacrylamide gel columns. J. Chromatogr. A 448, 41–53 (1988)

    Article  CAS  Google Scholar 

  126. Verleysen, K., Vandijck, J., Schelfaut, M., Sandra, P.: Enantiomeric separations in capillary electrophoresis using 18-crown-6-tetracarboxylic acid (18C6H4) as buffer additive. J. High Resolut. Chromatogr. 21, 323–331 (1998)

    Article  CAS  Google Scholar 

  127. Behr, J.-P., Girodeau, J.-M., Hayward, R.C., Lehn, J.-M., Sauvage, J.-P.: Molecular receptors. Functionalized and chiral macrocyclic polyethers derived from tartaric acid. Helv. Chim. Acta 63, 2096–2111 (1980)

    Article  CAS  Google Scholar 

  128. Kuhn, R., Wagner, J., Walbroeh, Y., Bereuter, T.: Potential and limitations of an optically active crown ether for chiral separation in capillary zone electrophoresis. Electrophoresis 15, 828–834 (1994)

    Article  CAS  Google Scholar 

  129. Nishi, H., Nakamura, K., Nakai, H., Sato, T.: Separation of enantiomers and isomers of amino compounds by capillary electrophoresis and high-performance liquid chromatography utilizing crown ethers. J. Chromatogr. A757, 225–235 (1997)

    Google Scholar 

  130. Mori, Y., Ueno, K., Umeda, T.: Enantiomeric separations of primary amino compounds by nonaqueous capillary zone electrophoresis with a chiral crown ether. J. Chromatogr. A 757, 328–332 (1997)

    Article  CAS  Google Scholar 

  131. Koide, T., Ueno, K.: Enantiomeric separations of primary amino compounds by capillary electrochromatography with monolithic chiral stationary phases of chiral crown ether-bonded negatively charged polyacrylamide gels. J. Chromatogr. A 909, 305–315 (2001)

    Article  CAS  Google Scholar 

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Mohammadzadeh Kakhki, R. Application of crown ethers as stationary phase in the chromatographic methods. J Incl Phenom Macrocycl Chem 75, 11–22 (2013). https://doi.org/10.1007/s10847-012-0158-0

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