Table of Contents Author Guidelines Submit a Manuscript
Bioinorganic Chemistry and Applications
Volume 2007, Article ID 65815, 16 pages
http://dx.doi.org/10.1155/2007/65815
Review Article

Lower-Rim Substituted Calixarenes and Their Applications

Department of Chemistry, School of Sciences, Gujarat University, Navrangpura, Ahmedabad 380009, Gujarat, India

Received 5 June 2006; Revised 12 December 2006; Accepted 30 January 2007

Academic Editor: Dimitris Kessisoglou

Copyright © 2007 Princy Jose and Shobana Menon. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. J. M. Lehn, Supramolecular Chemistry, Springer, Weinheim, Germany, 1995.
  2. C. J. Pedersen, “Cyclic polyethers and their complexes with metal salts,” Journal of the American Chemical Society, vol. 89, no. 26, pp. 7017–7036, 1967. View at Publisher · View at Google Scholar
  3. S. Shinkai, “Calixarenes—the third generation of supramolecules,” Tetrahedron, vol. 49, no. 40, pp. 8933–8968, 1993. View at Publisher · View at Google Scholar
  4. C. D. Gutsche, B. Dhawan, K. H. No, and R. Muthukrishnan, “Calixarenes. 4. The synthesis, characterization, and properties of the calixarenes from p-tert-butylphenol,” Journal of the American Chemical Society, vol. 103, no. 13, pp. 3782–3792, 1981. View at Publisher · View at Google Scholar
  5. A. Ikeda and S. Shinkai, “Novel cavity design using calix[n]arene skeletons: toward molecular recognition and metal binding,” Chemical Reviews, vol. 97, no. 5, pp. 1713–1734, 1997. View at Publisher · View at Google Scholar
  6. G. McMahon, S. O'Malley, K. Nolan, and D. Diamond, “Important calixarene derivatives—their synthesis and applications,” Arkivoc, vol. 2003, no. 7, pp. 23–31, 2003.
  7. W. Sliwa, “Calixarene complexes with transition metal, lanthanide and actinide ions,” Croatica Chemica Acta, vol. 75, no. 1, pp. 131–135, 2002.
  8. S. Menon, M. S. Gidwani, and Y. K. Agrawal, “Chromogenic calixarenes,” Reviews in Analytical Chemistry, vol. 22, no. 1, pp. 35–51, 2003.
  9. V. Böhmer and A. Shivanyuk, “Calixarenes in self-assembly phenomena,” in Calixarenes in Action, L. Mandolini and R. Ungaro, Eds., pp. 203–240, Imperial College Press, London, UK, 2000.
  10. C. D. Gutsche, “Calixarenes,” in Monographs in Supramolecular Chemistry, J. Stoddart, Ed., Royal Society of Chemistry, Cambridge, Mass, USA, 1989.
  11. A. Vigalok and T. M. Swager, “Conducting polymers of tungsten(VI)-oxo calixarene: intercalation of neutral organic guests,” Advanced Materials, vol. 14, no. 5, pp. 368–371, 2002. View at Publisher · View at Google Scholar
  12. W. Yang and M. M. de Villiers, “The solubilization of the poorly water soluble drug nifedipine by water soluble 4-sulphonic calix[n]arenes,” European Journal of Pharmaceutics and Biopharmaceutics, vol. 58, no. 3, pp. 629–636, 2004. View at Publisher · View at Google Scholar · View at PubMed
  13. W. Yang and M. M. de Villiers, “Aqueous solubilization of furosemide by supramolecular complexation with 4-sulphonic calix[n]arenes,” Journal of Pharmacy and Pharmacology, vol. 56, no. 6, pp. 703–708, 2004. View at Publisher · View at Google Scholar · View at PubMed
  14. M. O. Vysotsky, V. Böhmer, F. Würthner, C.-C. You, and K. Rissanen, “Calix[4]arene-functionalized naphthalene and perylene imide dyes,” Organic Letters, vol. 4, no. 17, pp. 2901–2904, 2002. View at Publisher · View at Google Scholar
  15. J. Seitz and G. Maas, “Calixarenes as ligands for transition-metal catalysts: a bis(calix[4]arene-11,23-dicarboxylato) dirhodium complex,” Chemical Communications, no. 4, pp. 338–339, 2002. View at Publisher · View at Google Scholar
  16. H. Miyaji, M. Dudic, and J. H. R. Tucker et al., “Bis(amidopyridine)-linked calix[4]arenes: a novel type of receptor for dicarboxylic acids,” Tetrahedron Letters, vol. 43, no. 5, pp. 873–878, 2002. View at Publisher · View at Google Scholar
  17. M. Lejeune, C. Jeunesse, D. Matt, N. Kyritsakas, R. Welter, and J.-P. Kintzinger, “Positioning of transition metal centres at the upper rim of cone-shaped calix[4]arenes. Filling the basket with an organometallic ruthenium unit,” Journal of the Chemical Society, Dalton Transactions, no. 8, pp. 1642–1650, 2002. View at Publisher · View at Google Scholar
  18. A. Arduini, G. Giorgi, A. Pochini, A. Secchi, and F. Ugozzoli, “Anion allosteric effect in the recognition of tetramethylammonium salts by calix[4]arene cone conformers,” Journal of Organic Chemistry, vol. 66, no. 25, pp. 8302–8308, 2001. View at Publisher · View at Google Scholar
  19. A. Akdoǧan, M. Deniz, S. Cebecioǧlu, A. Şen, and H. Deligöz, “Liquid-liquid extraction of transition metal cations by nine new azo derivatives calix[n]arene,” Separation Science and Technology, vol. 37, no. 4, pp. 973–980, 2002. View at Publisher · View at Google Scholar
  20. J.-Q. Lu and X.-W. He, Gaodeng Xuexiao Huaxue Xuebao, vol. 23, no. 2, p. 191, 2002.
  21. A. Dondoni, M. Kleban, X. Hu, A. Marra, and H. D. Banks, “Glycoside-clustering round calixarenes toward the development of multivalent carbohydrate ligands. Synthesis and conformational analysis of calix[4]arene O- and C-glycoconjugates,” Journal of Organic Chemistry, vol. 67, no. 14, pp. 4722–4733, 2002. View at Publisher · View at Google Scholar
  22. D. J. E. Spencer, B. J. Johnson, B. J. Johnson, and W. B. Tolman, “Calix[4]arenes linked to multiple bidentate N-donors: potential ligands for synthetic modeling of multinuclear metalloenzymes,” Organic Letters, vol. 4, no. 8, pp. 1391–1393, 2002. View at Publisher · View at Google Scholar
  23. V. K. Jain, A. Handa, R. Pandya, P. Shrivastav, and Y. K. Agrawal, “Polymer supported calix[4]arene-semicarbazone derivative for separation and preconcentration of La(III), Ce(III), Th(IV) and U(VI),” Reactive and Functional Polymers, vol. 51, no. 2-3, pp. 101–110, 2002. View at Publisher · View at Google Scholar
  24. J. Gagnon, M. Drouin, and P. D. Harvey, “Upper-rim functionalization of calix[4]arene by chloro(isocyanide)gold(I) groups: an entry to polymetallic architecture,” Inorganic Chemistry, vol. 40, no. 23, pp. 6052–6056, 2001. View at Publisher · View at Google Scholar
  25. E. A. Shokova, A. N. Khomich, and V. V. Kovalev, “Selective upper-rim adamantylation of calix[4]arenes,” Russian Journal of Organic Chemistry, vol. 37, no. 5, pp. 612–619, 2001. View at Publisher · View at Google Scholar
  26. B. König, T. Fricke, K. Gloe, and C. Chartroux, “Synthesis and metal-ion extraction properties of para-tert-butylcalixareneglycine ester acetamides,” European Journal of Inorganic Chemistry, vol. 1999, no. 9, pp. 1557–1562, 1999. View at Publisher · View at Google Scholar
  27. D. Q. Yuan, W. X. Zhu, R. J. Wang, M. X. Zhao, X. Yan, and Q. Y. Zheng, “Synthesis and crystal structure of a novel calix[8]arene ester derivative,” Chinese Chemical Letters, vol. 13, no. 1, pp. 37–40, 2002.
  28. S. Yamanaka and K. Sugata, Jpn. Kokai Tokyo. Koho JP 2002088003 AZ, March 2002, 13..
  29. S. Yamanaka and K. Sugata, Jpn. Kokai Tokyo. Koho JP 2002088017 AZ, March 2002, 11..
  30. K. Iwamoto, K. Araki, and S. Shinkai, “Syntheses of all possible conformational isomers of O-alkyl-p-t-butylcalix[4]arenes,” Tetrahedron, vol. 47, no. 25, pp. 4325–4342, 1991. View at Publisher · View at Google Scholar
  31. L. C. Groenen, B. H. M. Ruel, and A. Casnati et al., “Synthesis of monoalkylated calix[4]arenes via direct alkylation,” Tetrahedron, vol. 47, no. 39, pp. 8379–8384, 1991. View at Publisher · View at Google Scholar
  32. S. K. Sharma and C. D. Gutsche, “Selective lower rim reactions of 5,17-upper rim-disubstituted calix[4]arenes,” Journal of Organic Chemistry, vol. 61, no. 7, pp. 2564–2568, 1996. View at Publisher · View at Google Scholar
  33. H. Ross and U. Lüning, “Concave reagents—23. Synthesis of calix[6]arene bridged by a 1,l0-phenanthroline,” Tetrahedron Letters, vol. 38, no. 26, pp. 4539–4542, 1997. View at Publisher · View at Google Scholar
  34. V. Csokai, A. Grün, B. Balázs, G. Tóth, G. Horváth, and I. Bitter, “Unprecedented cyclizations of calix[4]arenes with glycols under the mitsunobu protocol—part 2.1 O,O-and O,S-bridged calixarenes,” Organic Letters, vol. 6, no. 4, pp. 477–480, 2004. View at Publisher · View at Google Scholar · View at PubMed
  35. K. Lu, Y.-J. Wu, Y.-J. Xing, D.-P. Zou, and Z.-X. Zhou, “Studies on the syntheses and properties of boronoalkoxycalix[4]arenes,” Chinese Journal of Chemistry, vol. 17, no. 6, pp. 674–683, 1999.
  36. E. A. Alekseeva, A. V. Mazepa, and A. I. Gren', “Synthesis and conformational characteristics of benzyl-substituted p-tert-butylcalixarenes,” Russian Journal of General Chemistry, vol. 71, no. 11, pp. 1786–1792, 2001. View at Publisher · View at Google Scholar
  37. C. Daniel, M. Mauro, R. Chris, K. Chitosi, Y. Akio, and O. Mikio, Australian Journal of Chemistry, vol. 52, p. 3227, 1999.
  38. T.-X. Yu, X.-J. Yang, Y.-J. Xiao, and Y.-B. He, “The synthesis of a few p-t-butycalix [4] arene diamides and its complexation with some ions,” Wuhan Daxue Xuebao, vol. 47, no. 4, pp. 393–395, 2001.
  39. A. Semwal, A. Bhattacharya, and S. K. Nayak, “Ultrasound mediated selective monoalkylation of 4-tert-butylcalix[6]arene at the lower rim,” Tetrahedron, vol. 58, no. 26, pp. 5287–5290, 2002. View at Publisher · View at Google Scholar
  40. M. Martino, L. Gregoli, C. Gaeta, and P. Neri, “Regioselective O-substitution of p-tert-butylcalix[7]arene,” Organic Letters, vol. 4, no. 9, pp. 1531–1534, 2002. View at Publisher · View at Google Scholar
  41. P. Neri, E. Battocolo, F. Cunsolo, C. Geraci, and M. Piattelli, “Study on the alkylation of p-tert-butylcalix[8]arene. Partially O-alkylated calix[8]arenes,” Journal of Organic Chemistry, vol. 59, no. 14, pp. 3880–3889, 1994. View at Publisher · View at Google Scholar
  42. P. Neri, C. Geraci, and M. Piattelli, “Tetra-O-benzylated calix[8]arenes with C4 symmetry,” Tetrahedron Letters, vol. 34, no. 20, pp. 3319–3322, 1993. View at Publisher · View at Google Scholar
  43. P. Neri, G. M. L. Consoli, F. Cunsolo, C. Rocco, and M. Piattelli, “Alkylation products of a calix[8]arene trianion. Effect of charge redistribution in intermediates,” Journal of Organic Chemistry, vol. 62, no. 13, pp. 4236–4239, 1997. View at Publisher · View at Google Scholar
  44. K. C. Honeychurch, J. P. Hart, D. C. Cowell, and D. W. M. Arrigan, “Voltammetric behavior and trace determination of cadmium at a calixarene modified screen-printed carbon electrode,” Electroanalysis, vol. 14, no. 3, pp. 177–185, 2002. View at Publisher · View at Google Scholar
  45. A. F. Danil de Namor, N. Al Rawi, O. E. Piro, E. E. Castellano, and E. Gil, “New lower rim calix(4)arene derivatives with mixed pendent arms and their complexation properties for alkali-metal cations. Structural, electrochemical, and thermodynamic characterization,” Journal of Physical Chemistry B, vol. 106, no. 4, pp. 779–787, 2002. View at Publisher · View at Google Scholar
  46. S. Shimizu, Y. Sasaki, and J. Okazaki, Jpn. kokai Tokkyo Koho JP 2002265405 AZ, September 2002, 17.
  47. F. Narumi, N. Morohashi, N. Matsumura, N. Iki, H. Kameyama, and S. Miyano, “Proximal O,O-capped calix[4]arenes with a disiloxane bridge as highly efficient synthetic intermediates for 1,2-dialkylation at the lower rim,” Tetrahedron Letters, vol. 43, no. 4, pp. 621–625, 2002. View at Publisher · View at Google Scholar
  48. F. D.-M. Ramírez, L. Charbonnière, G. Muller, R. Scopelliti, and J.-C. G. Bünzli, “A p-tert-butylcalix[4]arene functionalised at its lower rim with ether-amide pendant arms acts as an inorganic-organic receptor: structural and photophysical properties of its lanthanide complexes,” Journal of the Chemical Society, Dalton Transactions, no. 21, pp. 3205–3213, 2001. View at Publisher · View at Google Scholar
  49. B. Han, Y. Liu, Z. Chen, and R. Chen, Huaxue Tongbao, vol. 10, p. 41, 2000.
  50. J.-O. Dalbavie, J.-B. Regnouf-de-Vains, R. Lamartine, M. Perrin, S. Lecocq, and B. Fenet, “A calix[4]arene-based bipyridine podand as versatile ligand for transition metal cations,” European Journal of Inorganic Chemistry, vol. 2002, no. 4, pp. 901–909, 2002. View at Publisher · View at Google Scholar
  51. F. Oueslati, I. Dumazet-Bonnamour, and R. Lamartine, “Synthesis of new chromogenic 2,2-bithiazoylcalix[4]arenes,” Tetrahedron Letters, vol. 42, no. 46, pp. 8177–8180, 2001. View at Publisher · View at Google Scholar
  52. N. Psychogios and J.-B. Regnouf-de-Vains, “A new water-soluble calix[4]arene podand incorporating p-sulphonate groups and 2,2-bipyridine chelating units,” Tetrahedron Letters, vol. 43, no. 1, pp. 77–80, 2002. View at Publisher · View at Google Scholar
  53. Y.-J. Xing, Z.-X. Zhou, and Y.-J. Wu, “Syntheses and properties of new pendant-armed calix[4]arene derivatives as cesium selective ionophore,” Chinese Journal of Chemistry, vol. 19, no. 2, pp. 164–169, 2001.
  54. Y. Liu, B.-T. Zhao, H. Wang, Q.-F. Chen, and H.-Y. Zhang, Chinese Journal of Chemistry, vol. 19, no. 3, p. 281, 2001.
  55. A. Dondoni, A. Marra, M. Rossi, and M. Scoponi, “Synthesis and characterization of calix[4]arene-based copolyethers and polyurethanes. Ionophoric properties and extraction abilities towards metal cations of polymeric calix[4]arene urethanes,” Polymer, vol. 45, no. 18, pp. 6195–6206, 2004. View at Publisher · View at Google Scholar
  56. C. Wieser, D. Matt, J. Fischer, and A. Harriman, “Capping calixarenes with metallodiphosphine fragments: towards intracavity reactions,” Journal of the Chemical Society, Dalton Transactions, no. 14, pp. 2391–2402, 1997. View at Publisher · View at Google Scholar
  57. I. Bitter, A. Grün, B. Balázs, G. Tóth, G. Horváth, and L. Töke, “Studies on calix(aza)crowns. III. Synthesis of 1,3-alternate calix[4]arenes capped by diamide bridges,” Synthetic Communications, vol. 29, no. 22, pp. 3905–3917, 1999.
  58. Y. Liu, B.-T. Zhao, G. Huang, H.-Y. Zhang, and H. Wang, “An uncommon calix[4]azacrown-4 dimer assembled by hydrogen-bonded interaction,” Journal of Chemical Research, vol. 2001, no. 11, pp. 468–469, 2001.
  59. T. Tuntulani, V. Ruangpornvisuti, and N. Tantikunwatthana et al., “Synthesis of the tripodal-amine capped benzo crown p-tert-butylcalix[4]arene and its host-guest chemistry,” Tetrahedron Letters, vol. 38, no. 22, pp. 3985–3988, 1997. View at Publisher · View at Google Scholar
  60. K. Lu, Y.-J. Wu, Y.-J. Xing, D.-P. Zou, and Z.-X. Zhou, “Studies on the syntheses and properties of boronoalkoxycalix[4]arenes,” Chinese Journal of Chemistry, vol. 17, no. 6, pp. 674–683, 1999.
  61. W.-Z. Oh, K. W. Lee, and W. K. Choi et al., U.S. 6,040, 462 (C1 549-352;(070323/00)., March 2000, KR Appl. 9, 840, 327, 7, 1998.
  62. B. Pipoosananakaton, M. Sukwattanasinitt, N. Jaiboon, N. Chaichit, and T. Tuntulani, “New azobenzene crown p-tert-butylcalix[4]arenes as switchable receptors for Na+ and K+ ions: synthesis and isomerization studies,” Bulletin of the Korean Chemical Society, vol. 21, no. 9, pp. 867–874, 2000.
  63. W. Wąsikiewicz, M. Ślaski, G. Rokicki, V. Böhmer, C. Schmidt, and E. F. Paulus, “Crown ethers derived from bicyclocalix[4]arenes as chromoionophores,” New Journal of Chemistry, vol. 25, no. 4, pp. 581–587, 2001. View at Publisher · View at Google Scholar
  64. T. Tuntulani, G. Tumcharern, and V. Ruangpornvisuti, “Recognition studies of a pyridine-pendant calix[4]arene with neutral molecules: effects of non-covalent interactions on supramolecular structures and stabilities,” Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol. 39, no. 1-2, pp. 47–53, 2001. View at Publisher · View at Google Scholar
  65. P. A. Gale, J. L. Sessler, V. Lynch, and P. I. Sansom, “Synthesis of a new cylindrical calix[4]arene-calix[4]pyrrole pseudo dimer,” Tetrahedron Letters, vol. 37, no. 44, pp. 7881–7884, 1996. View at Publisher · View at Google Scholar
  66. G. De Salvo, G. Gattuso, A. Notti, M. F. Parisi, and S. Pappalardo, “Shape recognition of alkylammonium ions by 1,3-bridged calix[5]arene crown-6 ethers: endo- vs exo-cavity complexation,” Journal of Organic Chemistry, vol. 67, no. 3, pp. 684–692, 2002. View at Publisher · View at Google Scholar
  67. I. Jabin and O. Reinaud, “First C3v-symmetrical calix[6](aza)crown,” Journal of Organic Chemistry, vol. 68, no. 9, pp. 3416–3419, 2003. View at Publisher · View at Google Scholar · View at PubMed
  68. G. M. L. Consoli, C. Geraci, F. Cunsolo, and P. Neri, “Diester intrabridging of p-tert-butylcalix[8]arene and unexpected formation of the monospirodienone derivative,” Tetrahedron Letters, vol. 44, no. 1, pp. 53–56, 2003. View at Publisher · View at Google Scholar
  69. P. A. Gale, J. L. Sessler, V. Lynch, and P. I. Sansom, “Synthesis of a new cylindrical calix[4]arene-calix[4]pyrrole pseudo dimer,” Tetrahedron Letters, vol. 37, no. 44, pp. 7881–7884, 1996. View at Publisher · View at Google Scholar
  70. M. Kumar and V. Bhalla, “Synthesis of p-tert-butylcalix[4] arenes with diester bridge spanning the 1,3-(distal) positions on the lower rim,” Supramolecular Chemistry, vol. 12, no. 4, pp. 391–396, 2001.
  71. R. Arnecke, V. Böhmer, G. Ferguson, and S. Pappalardo, “Inherently chiral derivatives of calix[5]crowns,” Tetrahedron Letters, vol. 37, no. 9, pp. 1497–1500, 1996. View at Publisher · View at Google Scholar
  72. T. Saiki, K. Goto, N. Tokitoh, M. Goto, and R. Okazaki, “Syntheses and structures of novel m-xylylene-bridged calix[6]arenes: stabilization of a sulfenic acid in the cavity of calix[6]arene,” Journal of Organometallic Chemistry, vol. 611, no. 1-2, pp. 146–157, 2000. View at Publisher · View at Google Scholar
  73. C. Geraci, G. M. L. Consoli, M. Piattelli, and P. Neri, “Doubly bridged calix[8]crowns,” Collection of Czechoslovak Chemical Communications, vol. 69, no. 6, pp. 1345–1361, 2004. View at Publisher · View at Google Scholar
  74. C. Geraci, G. Chessari, M. Piattelli, and P. Neri, “Cation encapsulation within a ten-oxygen spheroidal cavity of conformationally preorganized 1,5-3,7-calix[8]bis-crown-3 derivatives,” Chemical Communications, no. 10, pp. 921–922, 1997. View at Publisher · View at Google Scholar
  75. S. E. Matthews, P. Schmitt, V. Felix, M. G. B. Drew, and P. D. Beer, “Calix[4]tubes: a new class of potassium-selective ionophore,” Journal of the American Chemical Society, vol. 124, no. 7, pp. 1341–1353, 2002. View at Publisher · View at Google Scholar
  76. Y.-B. He, H. Huang, L.-Z. Meng, C.-T. Wu, and T.-X. Yu, “New calix[4]crown diacylamides with fluorescent response to complexation with metal ions,” Chemistry Letters, vol. 28, no. 12, p. 1329, 1999. View at Publisher · View at Google Scholar
  77. D. J. Cram and J. M. Cram, “Design of complexes between synthetic hosts and organic guests,” Accounts of Chemical Research, vol. 11, no. 1, pp. 8–14, 1978. View at Publisher · View at Google Scholar
  78. E. B. Brouwer, K. A. Udachin, G. D. Enright, and J. A. Ripmeester, “Amine guest size and hydrogen-bonding influence the structures of p-tert-butylcalix[4]arene inclusions,” Chemical Communications, no. 19, pp. 1905–1906, 2000. View at Publisher · View at Google Scholar
  79. H.-J. Buschmann, L. Mutihac, and K. Jansen, “Complexation of some amine compounds by macrocyclic receptors,” Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol. 39, no. 1-2, pp. 1–11, 2001. View at Publisher · View at Google Scholar
  80. K. Linnemayr, E. R. Schmid, and G. Allmaier, “Characterization of calixarenes by positive- and negative-ion Californium-252 plasma desorption mass spectrometry,” Rapid Communications in Mass Spectrometry, vol. 11, no. 5, pp. 427–432, 1997. View at Publisher · View at Google Scholar
  81. A. Arduini, E. Ghidini, and A. Pochini et al., “p-t-Butylcalix[4]arene tetra-acetamide: a new strong receptor for alkali cations [1],” Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol. 6, no. 2, pp. 119–134, 1988. View at Publisher · View at Google Scholar
  82. S.-K. Chang, M. J. Jang, S. Y. Han, J. H. Lee, M. H. Kang, and K. T. No, “Molecular recognition of butylamines by calixarene-based ester ligands,” Chemistry Letters, vol. 21, no. 10, pp. 1937–1940, 1992. View at Publisher · View at Google Scholar
  83. P. D. Beer, Z. Chen, and P. A. Gale et al., “Cation recognition by new diester- and diamide-calix[4]arenediquinones and a diamide-benzo-15-crown-5-calix[4]arene,” Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol. 19, no. 1–4, pp. 343–359, 1994. View at Publisher · View at Google Scholar
  84. P. D. Beer, Z. Chen, and P. A. Gale, “Diester-calix[4]arenediquinone complexation and electrochemical recognition of group 1 and 2, ammonium and alkyl ammonium guest cations,” Tetrahedron, vol. 50, no. 3, pp. 931–940, 1994. View at Publisher · View at Google Scholar
  85. R. Ungaro, A. Pochini, G. D. Andreetti, and P. Domiano, “Molecular inclusion in functionalized macrocycles—part 10: crystal and molecular structure of a p-tert-butylcalix [6] arene hexapodand,” Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol. 3, no. 1, pp. 35–42, 1985. View at Publisher · View at Google Scholar
  86. R. Ungaro, A. Pochini, G. D. Andreetti, and F. Ugozzoli, “Molecular inclusion in functionalized macrocycles—part 12: crystal and molecular structure of ap-(1,1,3,3)-tetramethylbutylcalix[8]arene octapodand,” Journal of Inclusion Phenomena and Macrocyclic Chemistry, vol. 3, no. 4, pp. 409–420, 1985. View at Publisher · View at Google Scholar
  87. S. Harris, J. Diamond, D. Diamond, G. Barrett, and M. A. McKervey, IR Pat. Appl., p. S922577, 1997.
  88. R. Grady, T. Butler, B. MaCraith, D. Diamond, and M. A. McKervey, “Optical sensor for gaseous ammonia with tuneable sensitivity,” The Analyst, vol. 122, no. 8, pp. 803–806, 1997. View at Publisher · View at Google Scholar
  89. M. Loughran and D. Diamond, “Monitoring of volatile bases in fish sample headspace using an acidochromic dye,” Food Chemistry, vol. 69, no. 1, pp. 97–103, 2000. View at Publisher · View at Google Scholar
  90. A. Calestani, P. Minari, and A. Pochini et al., Israel Journal of Chemistry, vol. 2, p. 7, 1992.
  91. F. Arnaud-Neu, S. Fanni, and L. Guerra et al., “Cation complexation by chemically modified calixarenes—part 7: transport of alkali cations by p-tert-butylcalix[n]arene esters and amides,” Journal of the Chemical Society, Perkin Transactions 2, no. 1, pp. 113–118, 1995. View at Publisher · View at Google Scholar
  92. P. D. Beer, M. G. B. Drew, and M. I. Ogden, “First- and second-sphere co-ordination of a lanthanum cation by a calix[4]arene tetraamide in the partial-cone conformation,” Journal of the Chemical Society, Dalton Transactions, no. 9, pp. 1489–1492, 1997. View at Publisher · View at Google Scholar
  93. P. D. Beer, M. G. B. Drew, P. B. Leeson, and M. I. Ogden, “Versatile cation complexation by a calix[4]arene tetraamide (L). Synthesis and crystal structure of [ML][ClO4]2nMeCN (M = FeII, NiII, CuII, ZnII or PbII),” Journal of the Chemical Society, Dalton Transactions, no. 24, pp. 1273–1283, 1995. View at Publisher · View at Google Scholar
  94. P. D. Beer, M. G. B. Drew, M. Kan, P. B. Leeson, M. I. Ogden, and G. Williams, “Lanthanide structures, coordination, and extraction investigations of a 1,3-bis(diethyl amide)-substituted calix[4]arene ligand,” Inorganic Chemistry, vol. 35, no. 8, pp. 2202–2211, 1996. View at Publisher · View at Google Scholar
  95. P. D. Beer, M. G. B. Drew, and A. Grieve et al., “Neutral lanthanide di- and mono-meric complexes and selective extraction properties of a new 1,3-acid-diethyl amide substituted calix[4]arene ligand,” Chemical Communications, no. 10, pp. 1117–1118, 1996. View at Publisher · View at Google Scholar
  96. P. D. Beer, M. G. B. Drew, P. B. Leeson, and M. I. Ogden, “Metal complexes of a calix[4]arene diamide: syntheses, crystal structures and molecular mechanics calculations on [Fe(L1-2H)][FeCl4] and [Er(L1-2H)(picrate)] (L1 = 5,11,17,23-tetra-tert-butyl-25,27-bis(diethylcarbamoylmethoxy)calix[4]arene),” Inorganica Chimica Acta, vol. 246, no. 1-2, pp. 133–141, 1996. View at Publisher · View at Google Scholar
  97. M. A. Mckervey, M. J. Schwing-Weill, and F. Arnaud-Neu, “Cation binding by calixarenes,” in Comprehensive Supramalecular Chemistry, G. Gokek, Ed., vol. 1, pp. 537–603, Pergamon Press, Oxford, UK, 1996.
  98. G. Arena, A. Contino, A. Magri, D. Sciotto, and J. D. Lamb, in Abstracts of 4th International Conference on Calixarenes, p. 131, Parma, Italy, 1997.
  99. S. Fanni, F. Arnaud-Neu, M. A. McKervey, M.-J. Schwing-Weill, and K. Ziat, “Dramatic effects of p-dealkylation on the binding abilities of p-tert-butylcalix[6]arenes: new Cs+ and Sr2+ selective receptors,” Tetrahedron Letters, vol. 37, no. 44, pp. 7975–7978, 1996. View at Publisher · View at Google Scholar
  100. J. F. Dozol, A. Garcia-Carrera, V. Lamare, and H. Rouquette, “Extraction of trivalent actinides and long-lived fission products by different classes of functionalized calixarenes,” in Proceedings of the International Solvent Extraction Conference (ISEC '02), pp. 1168–1173, Cape Town, South Africa, March 2002.
  101. F. Cadogan, P. Kane, M. A. McKervey, and D. Diamond, “Lead-selective electrodes based on calixarene phosphine oxide derivatives,” Analytical Chemistry, vol. 71, no. 24, pp. 5544–5550, 1999. View at Publisher · View at Google Scholar
  102. G. Montavon, G. Duplâtre, Z. Asfari, and J. Vicens, “Solvent extraction of sodium and potassium ions by a tetra-carboxylated calix[4]arene,” New Journal of Chemistry, vol. 20, no. 10, pp. 1061–1069, 1996.
  103. R. Ludwig, K. Inoue, and T. Yamato, “Solvent extraction behaviour of calixarene-type cyclophanes towards trivalent La, Nd, Eu, Er, and Yb,” Solvent Extraction and Ion Exchange, vol. 11, no. 2, pp. 311–330, 1993.
  104. K. Ohto, M. Yano, and K. Inoue et al., “Solvent extraction of trivalent rare earth metal lons with carboxylate derivatives of calixarenes,” Analytical Sciences, vol. 11, no. 6, pp. 893–902, 1995.
  105. G. Montavon, G. Duplâtre, Z. Asfari, and J. Vicens, “Solvent extraction of uranium(VI) and thorium(IV) with a tetra-carboxylated calix[4]arene and effect of alkali ions (Na+, K+),” Solvent Extraction and Ion Exchange, vol. 15, no. 2, pp. 169–188, 1997.
  106. T. Nagasaki, S. Shinkai, and T. Matsuda, “Synthesis and solvent extraction properties of a novel calixarene-based uranophile bearing hydroxamate groups,” Journal of the Chemical Society, Perkin Transactions 1, no. 9, pp. 2617–2618, 1990. View at Publisher · View at Google Scholar
  107. T. Nagasaki and S. Shinkai, “Synthesis and solvent extraction studies of novel calixarene-based uranophiles bearing hydroxamic groups,” Journal of the Chemical Society, Perkin Transactions 2, no. 12, pp. 1063–1066, 1991. View at Publisher · View at Google Scholar
  108. Y. K. Agrawal and M. Sanyal, “Separation and determination of uranium(VI) with calixarene hydroxamic acids,” Journal of Radioanalytical and Nuclear Chemistry, vol. 198, no. 2, pp. 349–358, 1995. View at Publisher · View at Google Scholar
  109. A. T. Yordanov, O. M. Falana, H. F. Koch, and D. M. Roundhill, “(Methylthio)methyl and (N,N-dimethylcarbamoyl)methyl upper-rim-substituted calix[4]arenes as potential extractants for Ag(I), Hg(II), Ni(II), Pd(II), Pt(II), and Au(III),” Inorganic Chemistry, vol. 36, no. 27, pp. 6468–6471, 1997. View at Publisher · View at Google Scholar
  110. F. Arnaud-Neu, G. Barrett, and D. Corry et al., “Cation complexation by chemically modified calixarenes—part 10: thioamide derivatives of p-tert-butylcalix[4]-, [5]- and [6]-arenes with selectivity for copper, silver, cadmium and lead. X-Ray molecular structures of calix[4]arene thioamide-lead(II) and calix[4]arene amide-copper(II) complexes,” Journal of the Chemical Society, Perkin Transactions 2, no. 3, pp. 575–579, 1997. View at Publisher · View at Google Scholar
  111. K. N. Koh, T. Imada, T. Nagasaki, and S. Shinkai, “Molecular design of hard-soft ditopic metal-binding sites on a calix[4]arene platform,” Tetrahedron Letters, vol. 35, no. 24, pp. 4157–4160, 1994. View at Publisher · View at Google Scholar
  112. F. Arnand-Neu, V. Böhmer, and J.-F. Dozol et al., “Calixarenes with diphenylphosphoryl acetamide functions at the upper rim. A new class of highly efficient extractants for lanthanides and actinides,” Journal of the Chemical Society, Perkin Transactions 2, no. 6, pp. 1175–1182, 1996. View at Publisher · View at Google Scholar
  113. J. F. Malone, D. J. Mars, and M. A. Mckervey et al., “Calix[n]arene phosphine oxides. A new series of cation receptors for extraction of europium, thorium, plutonium and americium in nuclear waste treatment,” Journal of the Chemical Society, Chemical Communications, no. 20, pp. 2151–2153, 1995. View at Publisher · View at Google Scholar
  114. A. T. Yordanov, J. T. Mague, and D. M. Roundhill, “Solvent extraction of divalent palladium and platinum from aqueous solutions of their chloro complexes using an N,N-dimethyldithiocarbamoylethoxy substituted calix[4]arene,” Inorganica Chimica Acta, vol. 240, no. 1-2, pp. 441–446, 1995. View at Publisher · View at Google Scholar
  115. A. T. Yordanov, D. M. Roundhill, and J. T. Mague, “Extraction selectivites of lower rim substituted calix[4] arene hosts induced by variations in the upper rim substituents,” Inorganica Chimica Acta, vol. 250, no. 1-2, pp. 295–302, 1996. View at Publisher · View at Google Scholar
  116. M. Shortreed, E. Bakker, and R. Kopelman, “Miniature sodium-selective ion-exchange optode with fluorescent pH chromoionophores and tunable dynamic range,” Analytical Chemistry, vol. 68, no. 15, pp. 2656–2662, 1996. View at Publisher · View at Google Scholar
  117. J. S. Kim, I. Y. Yu, A. H. Suh, D. Y. Ra, and J. W. Kim, “Novel calix[4]arene azacrown ether,” Synthetic Communications, vol. 28, no. 16, pp. 2937–2944, 1998.
  118. J. S. Kim, in Abstracts of 5th International Conference on Calixarene Chemistry, vol. 9, p. 19, The University of Western Australia, Perth, Australia, 1999.
  119. J. S. Kim, O. J. Shon, J. W. Ko, M. H. Cho, I. Y. Yu, and J. Vicens, “Synthesis and metal ion complexation studies of proton-ionizable calix[4]azacrown ethers in the 1,3-alternate conformation,” Journal of Organic Chemistry, vol. 65, no. 8, pp. 2386–2392, 2000. View at Publisher · View at Google Scholar
  120. R. A. Sachleben, A. Urvoas, J. C. Bryan, T. J. Haverlock, B. A. Moyer, and B. P. Hay, “Dideoxygenated calix[4]arene crown-6 ethers enhanced selectivity for caesium over potassium and rubidium,” Chemical Communications, no. 17, pp. 1751–1752, 1999. View at Publisher · View at Google Scholar