Selective binding behaviors of p-sulfonatocalixarenes in aqueous solution

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 62, Issue 1-2, 2008, Pages 1-21

  Guo, Dong Sheng ^a   Wang, Kui ^a   Liu, Yu ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Complexation; p sulfonatocalixarenes; Structures; Thermodynamics

Indexed keywords

EID: 43749109580     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-008-9452-2     Document Type: Article

References (106)

1. (a) Gutsche, C.D.: Calixarenes revisited. In: Stoddart, J.F. (ed.) Monographs in Supramolecular Chemistry. Royal Society of Chemistry, Cambridge, UK (1998);
2. (b) Böhmer, V.: Calixarenes, macrocycles with (almost) unlimited possibilities. Angew. Chem. Int. Ed. Engl. 34, 713-745 (1995);
3. (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)
4. Pochini, A., Ungaro, R.: Calixarenes and related hosts. In: Vögtle, F. (ed.) Comprehensive Supramolecular Chemistry, vol. 2, pp. 103-149. Pergamon, Oxford (1996)
5. (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);
6. (b) Perret, F., Lazar, A.N., Coleman, A.W.: Biochemistry of the para-sulfonato-calix[n]arenes. Chem. Commun. 2425-2438 (2006);
7. (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)
8. 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)
9. Lamartine, R., Regnouf-de-Vains, J.-B., Choquar, P., Marcillac, A.: World Patent, WO 97/49677 (1997)
10. 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)
11. 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)
12. 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)
13. 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)
14. 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)
15. 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)
16. 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)
17. Makha, M., Raston, C.L.: Synthesis of p-benzylcalix[4]arene and its sulfonated water soluble derivative. Chem. Commun. 2470-2471 (2001)
18. 3+ 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)
19. 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)
20. 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)
21. 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)
22. 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)
23. 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)
24. 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)
25. Hayashi, K.: Kumamoto Institute of Technology Master's Thesis (1995)
26. 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)
27. 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)
28. Liu, Y., Yang, E.-C., Chen, Y.: Intermolecular complexation thermodynamics between water-soluble calix[4]arenes and diazacycloalkanes. Thermochim. Acta 429, 163-166 (2005)
29. 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)
30. 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)
31. 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)
32. 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)
33. 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)
34. 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)
35. 1H NMR, calorimetric, and molecular mechanics investigation. Chem. Eur. J. 5(2), 738-744 (1999)
36. 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)
37. 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)
38. 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)
39. 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)
40. 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)
41. 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)
42. 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)
43. 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)
44. 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)
45. Bird, C.L., Kuhn, A.T.: Electrochemistry of the viologens. Chem. Soc. Rev. 10, 49-82 (1981)
46. Summers, L.A.: The Bipyridinium Herbicides. Academic Press, New York (1980)
47. (a) Brun, A.M., Harriman, A.: Photochemistry of intercalated quaternary diazaaromatic salts. J. Am. Chem. Soc. 113(21), 8153-8159 (1991).
48. (b) Clennan, E.L.: Review viologen embedded zeolites. Coord. Chem. Rev. 248, 477-492 (2004)
49. Balzani, V., Credi, A., Raymo, F.M., Stoddart, J.F.: Artificial molecular machines. Angew. Chem. Int. Ed. 39, 3348-3391 (2000)
50. Monk, P.M.S.: The Viologens. Physicochemical Properties, Synthesis and Applications of the Salts of 4, 4′-Bipyridine. Wiley, Chichester, England (1998)
51. 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)
52. 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)
53. 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)
54. 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)
55. 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)
56. 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)
57. 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)
58. 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)
59. 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)
60. 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)
61. 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)
62. 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)
63. Tao, W., Barra, M.: Thermodynamic study of p-sulfonated calixarene complexes in aqueous solution. J. Chem. Soc. Perkin Trans. 2, 1957-1960 (1998)
64. Shinkai, S.: Calixarenes as new functionalized host molecules. Pure Appl. Chem. 58(11), 1523-1528 (1986)
65. 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)
66. 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)
67. 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)
68. 1H NMR investigation supported by molecular modeling. Org. Biomol. Chem. 4, 243-249 (2006)
69. 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)
70. 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)
71. 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)
72. 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)
73. 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)
74. 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)
75. 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)
76. 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)
77. 60 fullerene. Tetrahedron Lett. 45, 1387-1390 (2004);
78. 60 fullerene on its encapsulation by water soluble calixarenes. J. Incl. Phenom. Macrocycl. Chem. 60, 71-78 (2008)
79. 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)
80. 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)
81. 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)
82. Megyesi, M., Biczók, L.: Considerable fluorescence enhancement upon supramolecular complex formation between berberine and p-sulfonated calixarenes. Chem. Phys. Lett. 424, 71-76 (2006)
83. 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)
84. (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);
85. (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)
86. 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)
87. 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)
88. 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)
89. 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)
90. a shifts. Chem. Eur. J. 12, 4799-4807 (2006)
91. 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)
92. 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)
93. 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)
94. Hennig, A., Bakirci, H., Nau, W.M.: Label-free continuous enzyme assays with macrocycle-fluorescent dye complexes. Nat. Methods 4(8), 629-632 (2007)
95. 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)
96. 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)
97. 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)
98. 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)
99. 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)
100. 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)
101. 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)
102. 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)
103. 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)
104. Tao, W., Barra, M.: Inhibition of quinone-imine dye deamination by complexation with para-sulfonated calixarenes. J. Org. Chem. 66(6), 2158-2160 (2001)
105. Kaliappan, R., Kaanumalle, L.S., Natarajan, A., Ramamurthy, V.: Templating photodimerization of stilbazoles with water-soluble calixarenes. Photochem. Photobiol. Sci. 5, 925-930 (2006)
106. 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)