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Selective binding behaviors of p-sulfonatocalixarenes in aqueous solution

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Abstract

The complex structures, binding abilities, molecular selectivities, and thermodynamic origin of p-sulfonatocalixarenes upon complexation with kinds of guests are outlined in this review article, including inorganic cations, organic ammonium cations, pyridiniums and viologens, neutral organic molecules, dye molecules, and others. Calorimetric and spectroscopic investigations afford the complex stability constants, thermodynamic parameters and binding manners of the inclusion complexation of p-sulfonatocalixarenes with guest molecules. The π-stacking, hydrophobic and charge interactions are the main driving-forces during the course of the host–guest inclusion complexation. The molecular binding abilities and selectivities are influenced by not only the frameworks of calixarene cavities, structures of guest molecules, and their binding manners but also the conditions of solutions (mainly pH), which are discussed from the correlation between the structural features and molecular-recognition abilities. Moreover, the further applications and potentials of p-sulfonatocalixarenes are briefly described.

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References

  1. (a) Gutsche, C.D.: Calixarenes revisited. In: Stoddart, J.F. (ed.) Monographs in Supramolecular Chemistry. Royal Society of Chemistry, Cambridge, UK (1998); (b) Böhmer, V.: Calixarenes, macrocycles with (almost) unlimited possibilities. Angew. Chem. Int. Ed. Engl. 34, 713–745 (1995); (c) Ikeda, A., Shinkai, S.: Novel cavity design using calix[n]arene skeletons: toward molecular recognition and metal binding. Chem. Rev. 97(5), 1713–1734 (1997)

    Google Scholar 

  2. Pochini, A., Ungaro, R.: Calixarenes and related hosts. In: Vögtle, F. (ed.) Comprehensive Supramolecular Chemistry, vol. 2, pp. 103–149. Pergamon, Oxford (1996)

  3. (a) Atwood, J.L., Barbour, L.J., Hardie, M.J., Raston, C.L.: Metal sulfonatocalix[4,5]arene complexes: bi-layers, capsules, spheres, tubular arrays and beyond. Coord. Chem. Rev. 222, 3–32 (2001); (b) Perret, F., Lazar, A.N., Coleman, A.W.: Biochemistry of the para-sulfonato-calix[n]arenes. Chem. Commun. 2425–2438 (2006); (c) Dalgarno, S.J., Atwood, J.L., Raston, C.L.: Sulfonatocalixarenes: molecular capsule and ‘Russian doll’ arrays to structures mimicking viral geometry. Chem. Commun. 4567–4574 (2006)

    Google Scholar 

  4. Shinkai, S., Mori, S., Tsubaki, T., Sone, T., Manabe, O.: New water-soluble host molecules derived from calix[6]arene. Tetrahedron Lett. 25(46), 5315–5318 (1984)

    Article  CAS  Google Scholar 

  5. Lamartine, R., Regnouf-de-Vains, J.-B., Choquar, P., Marcillac, A.: World Patent, WO 97/49677 (1997)

  6. Shinkai, S., Araki, K., Tsubaki, T., Arimura, T., Manabe, O.: New synthesis of calixarene-p-sulphonates and p-nitrocalixarenes. J. Chem. Soc. Perkin Trans. 1, 2297–2299 (1987)

    Article  Google Scholar 

  7. Shinkai, S., Mori, S., Koreishi, H., Tsubaki, T., Manabe, O.: Hexasulfonated calix[6]arene derivatives: a new class of catalysts, surfactants, and host molecules. J. Am. Chem. Soc. 108(9), 2409–2416 (1986)

    Article  CAS  Google Scholar 

  8. Coquière, D., Cadeau, H., Rondelez, Y., Giorgi, M., Reinaud, O.: Ipso-chlorosulfonylation of calixarenes: a powerful tool for the selective functionalization of the large rim. J. Org. Chem. 71(11), 4059–4065 (2006)

    Article  Google Scholar 

  9. Silva, E.D., Coleman, A.W.: Synthesis and complexation properties towards amino acids of mono-substituted p-sulphonato-calix-[n]-arenes. Tetrahedron 59, 7357–7364 (2003)

    Article  Google Scholar 

  10. Arena, G., Casnati, A., Mirone, L., Sciotto, D., Ungaro, R.: A new water-soluble calix[4]arene ditopic receptor rigidified by microsolvation: acid–base and inclusion properties. Tetrahedron Lett. 38(11), 1999–2002 (1997)

    Article  CAS  Google Scholar 

  11. Makha, M., Raston, C.L.: Direct synthesis of calixarenes with extended arms: p-phenylcalix[4, 5, 6, 8]arenes and their water-soluble sulfonated derivatives. Tetrahedron Lett. 42, 6215–6217 (2001)

    Article  CAS  Google Scholar 

  12. Makha, M., McKinnon, I.R., Raston, C.L.: Synthesis and trans-β-carotenoid inclusion properties of a new class of water soluble calixarenes: J. Chem. Soc. Perkin Trans. 2, 1801–1806 (2002)

    Google Scholar 

  13. Makha, M., Raston, C.L.: Synthesis of p-benzylcalix[4]arene and its sulfonated water soluble derivative. Chem. Commun. 2470–2471 (2001)

  14. Iki, N., Horiuchi, T., Oka, H., Koyama, K., Morohashi, N., Kabuto, C., Miyano, S.: Energy transfer luminescence of Tb3+ ion complexed with calix[4]arenetetrasulfonate and the thia and sulfony analogue. The effect of bridging groups. J. Chem. Soc. Perkin Trans. 2, 2219–2225 (2001)

    Google Scholar 

  15. Bonal, C., Israëli, Y., Morel, J.-P., Morel-Desrosiers, N.: Binding of inorganic and organic cations by p-sulfonatocalix[4]arene in water: a thermodynamic study. J. Chem. Soc. Perkin Trans. 2, 1075–1078 (2001)

    Google Scholar 

  16. Morel, J.-P., Morel-Desrosiers, N.: Binding of monovalent metal cations by the p-sulfonatocalix[4]arene: experimental evidence for cation-π interactions in water. Org. Biomol. Chem. 4, 462–465 (2006)

    Article  CAS  Google Scholar 

  17. Liu, Y., Wang, H., Wang, L.-H., Zhang, H.-Y.: Complexation thermodynamics of water-soluble calix[4]arene derivatives with lanthanoid(III) nitrates in acidic aqueous solution. Thermochim. Acta 414, 65–70 (2004)

    Article  CAS  Google Scholar 

  18. Mendes, A., Bonal, C., Morel-Desrosiers, N., Morel, J.P., Malfreyt, P.: Molecular dynamics simulations of p-sulfonatocalix[4]arene complexes with inorganic and organic cations in water: a structure and thermodynamic study. J. Phys. Chem. B 106(17), 4516–4524 (2002)

    Article  CAS  Google Scholar 

  19. Sonoda, M., Hayashi, K., Nishida, M., Ishii, D., Yoshida, I.: Another uranophile sodium hydroxycalix[8]arene-p-sulfonate: its acid dissociation and divalent metal ion binding properties. Anal. Sci. 14, 493–499 (1998)

    Article  CAS  Google Scholar 

  20. Shinkai, S., Koreishi, H., Ueda, K., Arimura, T., Manabe, O.: Molecular design of calixarene-based uranophiles which exhibit remarkably high stability and selectivity. J. Am. Chem. Soc. 109(21), 6371–6376 (1987)

    Article  CAS  Google Scholar 

  21. Hayashi, K.: Kumamoto Institute of Technology Master’s Thesis (1995)

  22. Stödeman, M., Dhar, N.: Microcalorimetric titration of a tetra-p-sulfonated calix[4]arene with alkylammonium ions in aqueous solution. J. Chem. Soc. Faraday Trans. 94(7), 899–903 (1998)

    Article  Google Scholar 

  23. Stödeman, M., Dhar, N.: Microcalorimetric titration of a tetra-p-sulphonated calix[4]arene with α,ω-alkyl diammonium ions in an aqueous solution. Thermochim. Acta 320, 33–38 (1998)

    Article  Google Scholar 

  24. Liu, Y., Yang, E.-C., Chen, Y.: Intermolecular complexation thermodynamics between water-soluble calix[4]arenes and diazacycloalkanes. Thermochim. Acta 429, 163–166 (2005)

    Article  CAS  Google Scholar 

  25. Lehn, J.-M., Meric, R., Vigneron, J.-P., Cesario, M., Guilhem, J., Pascard, C., Asfari, Z., Vicens, J.: Binding of acetylcholine and other quaternary ammonium cations by sulfonated calixarenes. Crystal structure of a [choline-tetrasulfonated calix[4]arene] complex. Supramol. Chem. 5, 97–103 (1995)

    Article  CAS  Google Scholar 

  26. Shinkai, S., Araki, K., Matsuda, T., Nishiyama, N., Ikeda, H., Takasu, I., Iwamoto, M.: NMR and crystallographic studies of a p-sulfonatocalix[4]arene–guest complex. J. Am. Chem. Soc. 112(25), 9053–9058 (1990)

    Article  CAS  Google Scholar 

  27. Shinkai, S., Araki, K., Matsuda, T., Manabe, O.: NMR determination of association constants for aqueous calixarene complexes and guest template effects on the conformational freedom. Bull. Chem. Soc. Jpn. 62, 3856–3862 (1989)

    Article  CAS  Google Scholar 

  28. Arena, G., Gentile, S., Gulino, F.G., Sciotto, D., Sgarlata, C.: Water-soluble pentasulfonatocalix[5]arene: selective recognition of ditopic trimethylammonium cations by a triple non-covalent interaction. Tetrahedron Lett. 45, 7091–7094 (2004)

    Article  CAS  Google Scholar 

  29. Wang, L.-H., Guo, D.-S., Chen, Y., Liu, Y.: Thermodynamics of interactions between organic ammonium ions and sulfonatocalixarenes. Thermochim. Acta 443, 132–135 (2006)

    Article  CAS  Google Scholar 

  30. Arena, G., Casnati, A., Contino, A., Gulino, F.G., Sciotto, D., Ungaro, R.: Entropic origin of the sulfonate groups’ electrostatic assistance in the complexation of quaternary ammonium cations by water soluble calix[4]arenes. J. Chem. Soc. Perkin Trans. 2, 419–423 (2000)

    Google Scholar 

  31. Arena, G., Casnati, A., Contino, A., Lombardo, G.G., Sciotto, D., Ungaro, R.: Water-soluble calixarene hosts that specifically recognize the trimethylammonium group or the benzene ring of aromatic ammonium cations: a combined 1H NMR, calorimetric, and molecular mechanics investigation. Chem. Eur. J. 5(2), 738–744 (1999)

    Article  CAS  Google Scholar 

  32. Shinkai, S., Araki, K., Manabe, O.: NMR determination of association constants for calixarene complexes. Evidence for the formation of a 1:2 complex with calix[8]arene. J. Am. Chem. Soc. 110, 7214–7215 (1988)

    Article  CAS  Google Scholar 

  33. Ghoufi, A., Bonal, C., Morel, J.P., Morel-Desrosiers, N., Malfreyt, P.: Structures and energetics of complexes of the p-sulfonatocalix[4]arene with ammonium, alkylammonium, and tetraalkylammonium cations in water using molecular dynamics simulations. J. Phys. Chem. B 108(16), 5095–5104 (2004)

    Article  CAS  Google Scholar 

  34. Jin, T.: A new fluorometric method for the detection of the neurotransmitter acetylcholine in water using a dansylcholine complex with p-sulfonated calix[8]arene. J. Incl. Phenom. Macrocycl. Chem. 45, 195–201 (2003)

    Article  CAS  Google Scholar 

  35. Liu, Y., Yang, E.-C., Chen, Y., Guo, D.-S., Ding, F.: Molecular selective binding of pyridinium guest ions by water-soluble calix[4]arenes. Eur. J. Org. Chem. (21), 4581–4588 (2005)

  36. Liu, Y., Ma, Y.-H., Chen, Y., Guo, D.-S., Li, Q.: Molecular recognition thermodynamics of pyridine derivatives by sulfonatocalixarenes at different pH values. J. Org. Chem. 71(17), 6468–6473 (2006)

    Article  CAS  Google Scholar 

  37. Liu, Y., Guo, D.-S., Yang, E.-C., Zhang, H.-Y., Zhao, Y.-L.: The structure and thermodynamics of complexes between water-soluble calix[4]arenes and dipyridinium ions. Eur. J. Org. Chem. (1), 162–170 (2005)

  38. Liu, Y., Guo, D.-S., Zhang, H.-Y., Ma, Y.-H., Yang, E.-C.: The structure and thermodynamics of calix[n]arene complexes with dipyridines and phenanthroline in aqueous solution studied by microcalorimetry and NMR spectroscopy. J. Phys. Chem. B 110(7), 3428–3434 (2006)

    Article  CAS  Google Scholar 

  39. Liu, Y., Guo, D.-S., Zhang, H.-Y., Ding, F., Chen, K., Song, H.-B.: Supramolecular assemblies of sulfonatocalixarenes with phenanthroline: factors governing capsule formation versus bilayer arrangements. Chem. Eur. J. 13, 466–472 (2007)

    Article  CAS  Google Scholar 

  40. Barbour, L.J., Atwood, J.L.: Non-covalent interactions exert extraordinary influence over conformation and properties of a well-known supramolecular building block. Chem. Commun. 2020–2021 (2001)

  41. Bird, C.L., Kuhn, A.T.: Electrochemistry of the viologens. Chem. Soc. Rev. 10, 49–82 (1981)

    Article  CAS  Google Scholar 

  42. Summers, L.A.: The Bipyridinium Herbicides. Academic Press, New York (1980)

    Google Scholar 

  43. (a) Brun, A.M., Harriman, A.: Photochemistry of intercalated quaternary diazaaromatic salts. J. Am. Chem. Soc. 113(21), 8153–8159 (1991). (b) Clennan, E.L.: Review viologen embedded zeolites. Coord. Chem. Rev. 248, 477–492 (2004)

    Google Scholar 

  44. Balzani, V., Credi, A., Raymo, F.M., Stoddart, J.F.: Artificial molecular machines. Angew. Chem. Int. Ed. 39, 3348–3391 (2000)

    Article  CAS  Google Scholar 

  45. Monk, P.M.S.: The Viologens. Physicochemical Properties, Synthesis and Applications of the Salts of 4, 4′-Bipyridine. Wiley, Chichester, England (1998)

    Google Scholar 

  46. Bernardo, A.R., Lu, T., Córdova, E., Zhang, L., Gokel, G.W., Kaifer, A.E.: Host–guest complexation at the electrode/solution interface: the inclution of an amphiphilic viologen guest by an amphiphilic calix[6]arene host. J. Chem. Soc. Chem. Commun. 529–530 (1994)

  47. Castro, R., Godínez, L.A., Criss, C.M., Kaifer, A.E.: Host properties of α-cyclodextrin and a water-soluble calix[6]arene probed with dimeric bipyridinium guests. J. Org. Chem. 62(15), 4928–4935 (1997)

    Article  CAS  Google Scholar 

  48. Liu, Y., Wang, H., Zhang, H.-Y., Wang, L.-H.: Layered assembly formed by benzyl viologen and p-sulfonatothiacalix[4]arene and their complexation thermodynamics. Cryst. Growth Des. 5(1), 231–235 (2005)

    Article  CAS  Google Scholar 

  49. Guo, D.-S., Wang, L.-H., Liu, Y.: Highly effective binding of methyl viologen dication and its radical cation by p-sulfonatocalix[4, 5]arenes. J. Org. Chem. 72(20), 7775–7778 (2007)

    Article  CAS  Google Scholar 

  50. Arena, G., Casnati, A., Contino, A., Sciotto, D., Ungaro, R.: Charge assisted hydrophobic binding of ethanol into the cavity of calix[4]arene receptors in aqueous solution. Tetrahedron Lett. 38(26), 4685–4688 (1997)

    Article  CAS  Google Scholar 

  51. Arena, G., Contino, A., Gulino, F.G., Magrì, A., Sciotto, D., Ungaro, R.: Complexation of small neutral organic molecules by water soluble calix[4]arenes. Tetrahedron Lett. 41, 9327–9330 (2000)

    Article  CAS  Google Scholar 

  52. Ghoufi, A., Morel, J.P., Morel-Desrosiers, N., Malfreyt, P.: MD simulations of the binding of alcohols and diols by a calixarene in water: connections between microscopic and macroscopic properties. J. Phys. Chem. B 109(49), 23579–23587 (2005)

    Article  CAS  Google Scholar 

  53. Iki, N., Suzuki, T., Koyama, K., Kabuto, C., Miyano, S.: Inclusion behavior of thiacalix[4]arenetetrasulfonate toward water-miscible organic molecules studied by salting-out and X-ray crystallography. Org. Lett. 4(4), 509–512 (2002)

    Article  CAS  Google Scholar 

  54. Kunsági-Máté, S., Szabó, K., Bitter, I., Nagy, G., Kollár, L.: Unexpected effect of charge density of the aromatic guests on the stability of calix[6]arene-phenol host–guest complexes. J. Phys. Chem. A 109(23), 5237–5242 (2005)

    Article  Google Scholar 

  55. Baur, M., Frank, M., Schatz, J., Schildbach, F.: Water-soluble calix[n]arenes as receptor molecules for non-polar substrates and inverse phase transfer catalysts. Tetrahedron 57, 6985–6991 (2001)

    Article  CAS  Google Scholar 

  56. Kon, N., Iki, N., Miyano, S.: Inclusion behavior of water-soluble thiacalix- and calix[4]arenes towards substituted benzenes in aqueous solution. Org. Biomol. Chem. 1, 751–755 (2003)

    Article  CAS  Google Scholar 

  57. Liu, Y., Han, B.-H., Chen, Y.-T.: Molecular recognition and complexation thermodynamics of dye guest molecules by modified cyclodextrins and calixarenesulfonates. J. Phys. Chem. B 106(18), 4678–4687 (2002)

    Article  CAS  Google Scholar 

  58. Tao, W., Barra, M.: Thermodynamic study of p-sulfonated calixarene complexes in aqueous solution. J. Chem. Soc. Perkin Trans. 2, 1957–1960 (1998)

    Google Scholar 

  59. Shinkai, S.: Calixarenes as new functionalized host molecules. Pure Appl. Chem. 58(11), 1523–1528 (1986)

    Article  CAS  Google Scholar 

  60. Shinkai, S., Araki, K., Manabe, O.: Does the calixarene cavity recognise the size of guest molecules? On the ‘hole-size selectivity’ in water-soluble calixarenes. J. Chem. Soc. Chem. Commun. 187–189 (1988)

  61. Sueishi, Y., Inazumi, N., Hanaya, T.: Effects of pressure on inclusion complexation of methylene blue with water-soluble p-sulfonatocalix[n]arenes. J. Phys. Org. Chem. 18, 448–455 (2005)

    Article  CAS  Google Scholar 

  62. Douteau-Guével, N., Coleman, A.W., Morel, J.-P., Morel-Desrosiers, N.: Complexation of the basic amino acids lysine and arginine by three sulfonatocalix[n]arenes (n = 4, 6 and 8) in water: microcalorimetric determination of the Gibbs energies, enthalpies and entropies of complexation. J. Chem. Soc. Perkin Trans. 2, 629–633 (1999)

    Google Scholar 

  63. Arena, G., Casnati, A., Contino, A., Magrì, A., Sansone, F., Sciotto, D., Ungaro, R.: Inclusion of naturally occurring amino acids in water soluble calix[4]arenes: a microcalorimetric and 1H NMR investigation supported by molecular modeling. Org. Biomol. Chem. 4, 243–249 (2006)

    Article  CAS  Google Scholar 

  64. Buschmann, H.-J., Mutihac, L., Schollmeyer, E.: Complexation of some amino acids and peptides by p-sulfonatocalix[4]arene and hexasodium p-sulfonatocalix[6]arene in aqueous solution. J. Incl. Phenom. Macrocycl. Chem. 46, 133–137 (2003)

    Article  CAS  Google Scholar 

  65. Douteau-Guével, N., Perret, F., Coleman, A.W., Morel, J.-P., Morel-Desrosiers, N.: Binding of dipeptides and tripeptides cotaining lysine or arginine by p-sulfonatocalixarenes in water: NMR and microcalorimetric studies. J. Chem. Soc. Perkin Trans. 2, 524–532 (2002)

    Google Scholar 

  66. Millership, J.S.: A preliminary investigation of the solution complexation of 4-sulphonic calix[n]arenes with testosterone. J. Incl. Phenom. Macrocycl. Chem. 39, 327–331 (2001)

    Article  CAS  Google Scholar 

  67. Silva, E.D., Valmalle, C., Becchi, M., Cuilleron, C.-Y., Coleman, A.W.: The use of electrospray mass spectrometry (ES/MS) for the differential detection of some steroids as calix-[n]-arene sulphonate complexes. J. Incl. Phenom. Macrocycl. Chem. 46, 65–69 (2003)

    Article  Google Scholar 

  68. Fernandes, S.A., Cabeca, L.F., Marsaioli, A.J., de Paula, E.: Investigation of tetracaine complexation with beta-cyclodextrins and p-sulphonic acid calix[6]arenes by NOE and PGSE NMR. J. Incl. Phenom. Macrocycl. Chem. 57, 395–401 (2007)

    Article  CAS  Google Scholar 

  69. Zhou, Y., Lu, Q., Liu, C., She, S., Wang, L.: A novel spectrofluorimetric method for determination of lomefloxacin based on supramolecular inclusion complex between it and p-sulfonated calix[4]arene. Anal. Chim. Acta 552, 152–159 (2005)

    Article  CAS  Google Scholar 

  70. Silva, E.D., Rousseau, C.F., Zanella-Cléon, I., Becchi, M., Coleman, A.W.: Mass spectrometric determination of association constants of bovine serum albumin (BSA) with para-sulphonato-calix[n]arene derivatives. J. Incl. Phenom. Macrocycl. Chem. 54, 53–59 (2006)

    Article  Google Scholar 

  71. Memmi, L., Lazar, A., Brioude, A., Ball, V., Coleman, A.W.: Protein-calixarene interactions: complexation of bovine serum albumin by sulfonatocalix[n]arenes. Chem. Commun. 2474–2475 (2001)

  72. (a) Kunsági-Máté, S., Szabó, K., Bitter, I., Nagy, G., Kollár, L.: Complex formation between water-soluble sulfonated calixarenes and C60 fullerene. Tetrahedron Lett. 45, 1387–1390 (2004); (b) Kunsági-Máté, S., Vasapollo, G., Szabó, K., Bitter, I., Mele, G., Longo, L., Kollár, L.: Effect of covalent functionalization of C60 fullerene on its encapsulation by water soluble calixarenes. J. Incl. Phenom. Macrocycl. Chem. 60, 71–78 (2008)

    Google Scholar 

  73. Dalgarno, S.J., Fisher, J., Raston, C.L.: Interplay of p-sulfonatocalix[4]arene and crown ethers en route to molecular capsules and “Russian dolls”. Chem. Eur. J. 12, 2772–2777 (2006)

    Article  CAS  Google Scholar 

  74. Alvarez, J., Wang, Y., Ong, W., Kaifer, A.E.: Temperature, solvent, proton transfer and complexation effects on the conformational flexibility of the anionic host calix[6]arenesulfonate. J. Supramol. Chem. 1, 269–274 (2001)

    Article  CAS  Google Scholar 

  75. Chiba, M., Kim, H.-B., Kitamura, N.: Spectroscopic and photophysical responses of a ruthenium(II) dication-calix[4]arenetetrasulfonate hybrid complex upon ion binding. J. Photochem. Photobiol. A 151, 67–74 (2002)

    Article  CAS  Google Scholar 

  76. Megyesi, M., Biczók, L.: Considerable fluorescence enhancement upon supramolecular complex formation between berberine and p-sulfonated calixarenes. Chem. Phys. Lett. 424, 71–76 (2006)

    Article  CAS  Google Scholar 

  77. Costanzo, L.D., Geremia, S., Randaccio, L., Purrello, R., Lauceri, R., Sciotto, D., Gulino, F.G., Pavone, V.: Calixarene-porphyrin supramolecular complexes: pH-tuning of the complex stoichiometry. Angew. Chem. Int. Ed. 40(22), 4245–4247 (2001)

    Article  Google Scholar 

  78. (a) Moschetto, G., Lauceri, R., Gulino, F.G., Sciotto, D., Purrello, R.: Non-covalent synthesis in aqueous solution of discrete multi-porphyrin aggregates with programmable stoichiometry and sequence. J. Am. Chem. Soc. 124(49), 14536–14537 (2002); (b) Gulino, F.G., Lauceri, R., Frish, L., Evan-Salem, T., Cohen, Y., Zorzi, R.D., Geremia, S., Costanzo, L.D., Randaccio, L., Sciotto, D., Purrello, R.: Noncovalent synthesis in aqueous solution and spectroscopic characterization of multi-porphyrin complexes. Chem. Eur. J. 12, 2722–2729 (2006)

    Google Scholar 

  79. Fiammengo, R., Timmerman, P., de Jong, F., Reinhoudt, D.N.: Highly stable cage-like complexes by self-assembly of tetracationic Zn(II) porphyrinates and tetrasulfonatocalix[4]arenes in polar solvents. Chem. Commun. 2313–2314 (2000)

  80. Fiammengo, R., Wojciechowski, K., Crego-Calama, M., Timmerman, P., Figoli, A., Wessling, M., Reinhoudt, D.N.: Heme-protein active site models via self-assembly in water. Org. Lett. 5(19), 3367–3370 (2003)

    Article  CAS  Google Scholar 

  81. Lang, K., Kubát, P., Lhoták, P., Mosinger, J., Wagnerová, D.M.: Photophysical properties and photoinduced electron transfer within host–guest complexes of 5, 10, 15, 20-tetrakis(4-N-methylpyridyl) porphyrin with water-soluble calixarenes and cyclodextrins. Photochem. Photobiol. 74(4), 558–565 (2001)

    Article  CAS  Google Scholar 

  82. Bakirci, H., Koner, A.L., Nau, W.M.: Spherical shape complementarity as an overriding motif in the molecular recognition of noncharged organic guests by p-sulfonatocalix[4]arene: complexation of bicyclic azoalkanes. J. Org. Chem. 70(24), 9960–9966 (2005)

    Article  CAS  Google Scholar 

  83. Bakirci, H., Koner, A.L., Schwarzlose, T., Nau, W.M.: Analysis of host-assisted guest protonation exemplified for p-sulfonatocalix[4]arene–towards enzyme-mimetic pK a shifts. Chem. Eur. J. 12, 4799–4807 (2006)

    Article  CAS  Google Scholar 

  84. Bakirci, H., Koner, A.L., Nau, W.M.: Binding of inorganic cations by p-sulfonatocalix[4]arene monitored through competitive fluorophore displacement in aqueous solution. Chem. Commun. 5411–5413 (2005)

  85. Bakirci, H., Nau, W.M.: Fluorescence regeneration as a signaling principle for choline and carnitine binding: a refined supramolecular sensor system based on a fluorescent azoalkane. Adv. Funct. Mater. 16, 237–242 (2006)

    Article  CAS  Google Scholar 

  86. Bakirci, H., Koner, A.L., Dickman, M.H., Kortz, U., Nau, W.M.: Dynamically self-assembling metalloenzyme models based on calixarenes. Angew. Chem. Int. Ed. 45, 1–5 (2006)

    Article  Google Scholar 

  87. Hennig, A., Bakirci, H., Nau, W.M.: Label-free continuous enzyme assays with macrocycle-fluorescent dye complexes. Nat. Methods 4(8), 629–632 (2007)

    Article  CAS  Google Scholar 

  88. Koh, K.N., Araki, K., Ikeda, A., Otsuka, H., Shinkai, S.: Reinvestigation of calixarene-based artificial-signaling acetylcholine receptors useful in neutral aqueous (water/methanol) solution. J. Am. Chem. Soc. 118(4), 755–758 (1996)

    Article  CAS  Google Scholar 

  89. Liu, C., Fu, Z., Yu, H., Xu, H., Wang, L., Zhou, Y.: Spectrofluorimetric study on the inclusion behavior of p-sulfonated calix[6]arene with cetyltrimethylammonium bromide and analytical application. J. Lumin. 126, 747–752 (2007)

    Article  CAS  Google Scholar 

  90. Mousavi, Z., Bobacka, J., Ivaska, A.: Potentiometric Ag+ sensors based on conducting polymers: a comparison between poly(3, 4-ethylenedioxythiophene) and polypyrrole doped with sulfonated calixarenes. Electroanalysis 17(18), 1609–1615 (2005)

    Article  CAS  Google Scholar 

  91. Lu, Q., Callahan, J.H., Collins, G.E.: The selective detection of uranium(VI) on a microchip using a derivatized 4-sulfonic calix[6]arene. Chem. Commun. 1913–1914 (2000)

  92. Souchon, V., Leray, I., Valeur, B.: Selective detection of cesium by a water-soluble fluorescent molecular sensor based on a calix[4]arene-bis(crown-6-ether). Chem. Commun. 4224–4226 (2006)

  93. Nishida, M., Kondo, H., Sonoda, M., Ishii, D., Yoshida, I.: Highly selective solvent extraction of uranyl ion using super uranophiles in the presence of methyltrioctylammonium chloride. Bull. Chem. Soc. Jpn. 73(8), 1823–1829 (2000)

    Article  CAS  Google Scholar 

  94. Horiuchi, T., Iki, N., Oka, H., Miyano, S.: Highly selective luminescence determination of terbium at the sub-ppb level with sulfonylcalix[4]arene-p-tetrasulfonate. Bull. Chem. Soc. Jpn. 75(12), 2615–2619 (2002)

    Article  CAS  Google Scholar 

  95. Xu, H., Yu, X.-D., Chen, H.-Y.: Partial filling technique in capillary electrophoresis for the separation of phenolic isomers with sulfonatocalix[4]arene as a selector. Electrophoresis 24, 4254–4263 (2003)

    Article  CAS  Google Scholar 

  96. Goto, K., Yano, Y., Okada, E., Liu, C.-W., Yamamoto, K., Ueoka, R.: Catalytic specificity exhibited by p-sulfonatocalix[n]arenes in the methanolysis of N-acetyl-L-amino acids. J. Org. Chem. 68(3), 865–870 (2003)

    Article  CAS  Google Scholar 

  97. Tao, W., Barra, M.: Inhibition of quinone-imine dye deamination by complexation with para-sulfonated calixarenes. J. Org. Chem. 66(6), 2158–2160 (2001)

    Article  CAS  Google Scholar 

  98. Kaliappan, R., Kaanumalle, L.S., Natarajan, A., Ramamurthy, V.: Templating photodimerization of stilbazoles with water-soluble calixarenes. Photochem. Photobiol. Sci. 5, 925–930 (2006)

    Article  CAS  Google Scholar 

  99. Anantachoke, N., Makha, M., Raston, C.L., Reutrakul, V., Smith, N.C., Saunders, M.: Fine tuning the production of nanosized β-carotene particles using spinning disk processing. J. Am. Chem. Soc. 128(42), 13847–13853 (2006)

    Article  CAS  Google Scholar 

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Acknowledgements

This work was supported by NNSFC (Nos. 20421202, 20673061 and 20703025), Special Fund for Doctoral Program from Ministry of Education of China (No. 20050055004) and 111 Project (No. B06005), which are gratefully acknowledged.

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  1. Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, People’s Republic of China

    Dong-Sheng Guo, Kui Wang & Yu Liu

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  1. Dong-Sheng Guo
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  2. Kui Wang
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  3. Yu Liu
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Correspondence to Yu Liu.

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Guo, DS., Wang, K. & Liu, Y. Selective binding behaviors of p-sulfonatocalixarenes in aqueous solution. J Incl Phenom Macrocycl Chem 62, 1–21 (2008). https://doi.org/10.1007/s10847-008-9452-2

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  • DOI: https://doi.org/10.1007/s10847-008-9452-2

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