New Ionophoric Calix[4]diquinones: Coordination Chemistry, Electrochemistry, and X-ray Crystal Structures

Inorganic Chemistry

Volumn 36, Issue 25, 1997, Pages 5880-5893

  Beer, Paul D ^a   Gale, Philip A ^a   Chen, Zheng ^a,b   Drew, Michael G B ^c   Heath, Jennifer A ^a   Ogden, Mark I ^a,d   Powell, Harold R ^e  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^c UNIVERSITY OF READING   (United Kingdom)

^d CURTIN UNIVERSITY   (Australia)

^e CAMBRIDGE CRYSTALLOGRAPHIC DATA CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000086680     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (68)

1. (a) Kaifer, A.; Echegoyen, L. In Cation Binding by Macrocyclic Systems; Inoue, Y., Gokel, G. W., Eds.; Marcel Dekker: New York, 1990; p 363.
2. (b) Beer, P. D. Adv. Inorg. Chem. 1992, 39, 79.
3. Beer, P. D. Adv. Mater. 1994, 6, 607.
4. Beer, P. D.; Gale, P. A.; Chen, Z. Adv. Phys. Org. Chem., in press.
5. (a) Hall C. D.; Sharpe, N. W.; Danks, I. P.; Sang, Y. P. J. Chem. Soc., Chem. Commun. 1989, 419.
6. (b) Fu, E.; Green, M. L. H.; Lowe, V. J.; Marder, S. R. J. Organomet. Chem. 1988, 341, C39.
7. Lowe, N. D.; Garner, C. D. J. Chem. Soc., Dalton Trans. 1993, 2197.
8. van Veggel, F. C. J. M.; Harkema, S.; Bos, M.; Verboom, W.; Woolthius, G. K.; Reinhoudt, D. N. J. Org. Chem. 1989, 54, 2351.
9. (e) Hall, C. D.; Tucker, J. H. R.; Chu, S. Y. F.; Parkins, A. W.; Nyburg, S. C. J. Chem. Soc., Chem. Commun. 1993, 1505.
10. (f) Plenio, H.; Diodone, R. Inorg. Chem. 1995, 34, 3964.
11. (g) Medina, J. C.; Goodnow, T. T.; Rojas, M. T.; Atwood, J. L.; Lynn, B. C.; Kaifer, A. E.; Gokel, G. W. J. Am. Chem. Soc. 1992, 114, 10583.
12. (a) Beer, P. D.; Kocian, O.; Mortimer, R. J.; Ridgway, C. J. Chem. Soc., Dalton Trans. 1993, 2629.
13. (b) Beer, P. D.; Chen, Z.; Ogden, M. I. J. Chem. Soc., Faraday Trans. 1995, 91, 295.
14. Beer, P. D.; Kocian, O.; Mortimer, R. J.; Ridgway, C.; Stradiotto, N. R. J. Electroanal. Chem. 1996, 408, 61.
15. (a) Delgado, M.; Gustowski, D. A.; Yoo, H. K.; Gatto, V. J.; Gokel, G. W.; Echegoyen, L. J. Am. Chem. Soc. 1988, 110, 119.
16. (b) Gustowski, D. A.; Delgado, M.; Gatto, V. J.; Echegoyen, L.; Gokel, G. W. J. Am. Chem. Soc. 1986, 108, 7553.
17. Delgado, M.; Wolf, R. E., Jr.; Hartman, J. R.; McCafferty, G.; Yagbasan, R.; Rawle, S. C.; Watkin, D. J.; Cooper, S. R. J. Am. Chem. Soc. 1992, 114, 8983.
18. Bethell, D.; Dougherty, G.; Cupertino, D. C. J. Chem. Soc., Chem. Commun. 1995, 675.
19. (a) Kaifer, A. E.; Echegoyen, L.; Gustowski, D. A.; Goli, D. M.; Gokel, G. W. J. Am. Chem. Soc. 1983, 105, 7168.
20. (b) Kaifer, A. E.; Gustowski, D. A.; Echegoyen, L.; Gatto, V. J.; Schultz, R. A.; Cleary, T. P.; Morgan, C. R.; Goli, D. M.; Rios, A. M.; Gokel, G. W. J. Am. Chem. Soc. 1985, 107, 1958.
21. (a) Otsubo, T.; Ogura, F. Bull. Chem. Soc. Jpn. 1985, 58, 1343.
22. (b) Jørgensen, T.; Hansen, T. K.; Becker, J. Chem. Soc. Rev. 1994, 41 and references cited therein.
23. (a) Gutsche, C. D. Calixarenes: Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, U.K., 1989.
24. (b) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
25. (a) Collins, E. M.; McKervey, M. A.; Madigan, E.; Moran, M. B.; Owens, M.; Ferguson, G.; Harris, S. J. J. Chem. Soc., Perkin Trans. 1 1991, 3137 and references cited therein,
26. (b) Arnaud-Neu, F.; Barrett, G.; Harris, S. J.; Owens, M.; McKervey, M. A.; Schwing-Weill, M.-J.; Schwinté, P. Inorg. Chem. 1993, 32, 2644.
27. Dijkstra, P. J.; Brunink, J. A. J.; Bugge, K. E.; Reinhoudt, D. N.; Harkema, S.; Ungaro, R.; Ugozzoli, F.; Ghidini, E. J. Am. Chem. Soc. 1989, 111, 7567.
28. (a) Floriani, C.; Jacoby, D.; Chiesi-Villa, A.; Guastini, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 1376.
29. (b) Moran, J. K.; Roundhill, D. M. Inorg. Chem. 1992, 31, 4213.
30. Loeber, C.; Matt, D.; De Cian, A.; Fischer, J. J. Organomet. Chem. 1994, 475, 297.
31. Beer, P. D.; Martin, J. P.; Drew, M. G. B. Tetrahedron 1992, 48, 9917.
32. (e) Regnouf de Vains, J.-B.; Lamartine, R. Helv. Chim. Acta 1994, 77, 1817.
33. (f) Beer, P. D.; Chen, Z.; Goulden, A. J.; Grieve, A.; Hesek, D.; Szemes, F.; Wear, T. J. Chem. Soc., Chem. Commun. 1994, 1269.
34. (a) Sabbatini, N.; Guardigli, M.; Mecati, A.; Balzani, V.; Ungaro, R.; Ghidini, E.; Casnati, A.; Pochini, A. J. Chem. Soc., Chem. Commun. 1990, 878.
35. (b) Sabbatini, N.; Guardigli, M.; Mannet, I.; Ungaro, R.; Casnati, A.; Fischer, C.; Ziessel, R.; Ulrich, G. New J. Chem. 1995, 19, 137.
36. Rudkevich, D. M.; Verboom, W.; van der Tol, E.; van Staveren, C. J.; Kaspersen, F. M.; Verhoeven, J. W.; Reinhoudt, D. N. J. Chem. Soc., Perkin Trans. 2 1995, 131.
37. Arnaud-Neu, F. Chem. Soc. Rev. 1994, 235 and references cited therein,
38. (e) Beer, P. D.; Drew, M. G. B.; Kan, M.; Leeson, P. B.; Ogden, M. I.; Williams, G. Inorg. Chem. 1996, 35, 2202.
39. (f) Beer, P. D.; Drew, M. G. B.; Grieve, A.; Kan, M.; Leeson, P. B.; Nicholson, G.; Ogden, M. I.; Williams, G. Chem. Commun. 1996, 1117.
40. Diamond, D.; McKervey, M. A. Chem. Soc. Rev. 1996, 15.
41. (a) Morita, Y.; Agawa, T.; Kai, Y.; Kanehisa, N.; Kasai, N.; Nomura, E.; Taniguchi, H. Chem. Lett. 1989, 1349.
42. (b) Morita, Y.; Agawa, T.; Nomura, E.; Taniguchi, H. J. Org. Chem. 1992, 57, 3658.
43. Suga, K.; Fujihira, M.; Morita, Y.; Agawa, T. J. Chem. Soc., Faraday Trans. 1991, 1575.
44. Reddy, P. A.; Kashyap, R. P.; Watson, W. H.; Gutsche, C. D. Isr. J. Chem. 1992, 32, 89.
45. (e) Reddy, P. A.; Gutsche, C. D. J. Org. Chem. 1993, 58, 3245.
46. (a) Gómez-Kaifer, M.; Reddy, P. A.; Gutsche, C. D.; Echegoyen, L. J. Am. Chem. Soc. 1994, 116, 3580.
47. (b) Bettega, H. C. Y.; Moutet, J. C.; Ulrich, G.; Ziessel, R. J. Electroanal. Chem. 1996, 406, 247.
48. Preliminary aspects of this work have been published previously: (a) Beer, P. D.; Chen, Z.; Gale, P. A. Tetrahedron 1994, 50, 931. (b) Beer, P. D.; Chen, Z.; Drew, M. G. B.; Gale, P. A. J. Chem. Soc., Chem. Commun. 1994, 2207. (c) Chen, Z.; Gale, P. A.; Heath, J. A.; Beer, P. D. J. Chem. Soc., Faraday Trans. 1994, 2931.
49. Preliminary aspects of this work have been published previously: (a) Beer, P. D.; Chen, Z.; Gale, P. A. Tetrahedron 1994, 50, 931. (b) Beer, P. D.; Chen, Z.; Drew, M. G. B.; Gale, P. A. J. Chem. Soc., Chem. Commun. 1994, 2207. (c) Chen, Z.; Gale, P. A.; Heath, J. A.; Beer, P. D. J. Chem. Soc., Faraday Trans. 1994, 2931.
50. Preliminary aspects of this work have been published previously: (a) Beer, P. D.; Chen, Z.; Gale, P. A. Tetrahedron 1994, 50, 931. (b) Beer, P. D.; Chen, Z.; Drew, M. G. B.; Gale, P. A. J. Chem. Soc., Chem. Commun. 1994, 2207. (c) Chen, Z.; Gale, P. A.; Heath, J. A.; Beer, P. D. J. Chem. Soc., Faraday Trans. 1994, 2931.
51. The computer program used to calculate the stability constants was SPECFIT v 2.02, Spectrum Software Associates, Chapel Hill, NC.
52. McKillop, A.; Swann, B. P.; Taylor, E. C. Tetrahedron 1970, 26, 4031.
53. Ghidini, E.; Ugozzoli, F.; Ungaro, R.; Harkema, S.; El-Fadl, A. A.; Reinhoudt, D. N. J. Am. Chem. Soc. 1990, 112, 6979.
54. Wolsey, W. C. J. Chem. Educ. 1973, 50, A335.
55. It has been noted in the literature that elemental analysis of calixarene-containing compounds frequently produces erroneous results. For examples see: (a) Gutsche, C. D.; See, K. A. J. Org. Chem. 1992, 57, 4527. (b) Böhmer, V.; Jung, K.; Schön, M.; Wolff, A. J. Org. Chem. 1992, 57, 790.
56. It has been noted in the literature that elemental analysis of calixarene-containing compounds frequently produces erroneous results. For examples see: (a) Gutsche, C. D.; See, K. A. J. Org. Chem. 1992, 57, 4527. (b) Böhmer, V.; Jung, K.; Schön, M.; Wolff, A. J. Org. Chem. 1992, 57, 790.
57. Kabsch, W. J. Appl. Crystallogr. 1988, 21, 916.
58. R-Axis data reduction program; Molecular Structure Corp., The Woodlands, TX.
59. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J. Appl. Crystallogr. 1993, 26, 343.
60. Sheldrick, G. M. SHELXS-86. Acta Crystallogr. 1990, A46, 467.
61. Sheldrick, G. M. SHELXL-93, Program for Crystal Structure Refinement; University of Gottingen, Gottingen, Germany, 1993.
62. Watkin, D. J.; Carruthers, R. J.; Betteridge, P. Crystals; Chemical Crystallography Laboratory: Oxford, U.K., 1985.
63. McKillop, A.; Turrell, A. G.; Young, D. W.; Taylor, E. C. J. Am. Chem. Soc. 1980, 102, 6504.
64. Taylor, E. C.; Andrade, J. G.; Rall, G. J. H.; McKillop, A. J. Am. Chem. Soc. 1980, 102, 6513.
65. Beer, P. D.; Drew, M. G. B.; Gale, P. A.; Leeson, P. B.; Ogden, M. I. J. Chem. Soc., Dalton Trans. 1994, 3479.
66. Casnati, A.; Cornell], E.; Fabbi, M.; Bocchi, V.; Mori, G.; Ugozzoli, F.; Lanfredi, A. M. M.; Pochini, A.; Ungaro, R. Recl. Trav. Chim. Pays-Bas 1993, 112, 384.
67. Hynes, M. J. J. Chem. Soc., Dalton Trans. 1993, 311.
68. Osteryoung, J.; O'Dea, J. J. In Electroanalytical Chemistry; Bard, A. J., Ed.; Dekker: New York, 1987; Vol. 14, p 209.