Meldola Medal Lecture. Redox responsive macrocyclic receptor molecules containing transition metal redox centres

Chemical Society Reviews

Volumn 18, Issue , 1989, Pages 409-450

  Beer, Paul D ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845286954     PISSN: 03060012     EISSN: None     Source Type: Journal    
DOI: 10.1039/CS9891800409     Document Type: Conference Paper

References (111)

1. (a) C. J. Pedersen, J. Am. Chem. Soc, 1967, 89, 7017
2. (b) C. J. Pedersen, Aldrichim. Acta, 1971,4, 1.
3. C. J. Pedersen, (Nobel Lecture), Angew. Chem., Int. Ed. Engl., 1988, 27, 1021.
4. J. M. Lehn, ‘Structure and Bonding’, Springer Verlag, Berlin, 1973, p. 1
5. (b) B. Dietrich, J. M. Lehn and J. P. Sauvage, Tetrahedron Lett., 1969, 2885.
6. J. M. Lehn, (Nobel Lecture), Angew. Chem., Int. Ed. Engl., 1988, 27, 89.
7. D. J. Cram, (Nobel Lecture), Angew. Chem., Int. Ed. Engl, 1988, 27, 1009.
8. ‘Synthesis of Macrocycles’, Progress in Macrocyclic Chemistry, Vol. 3, ed. R. M. Izatt and J. J. Christensen, J. Wiley, New York, 1987.
9. ‘Synthetic Multidentate Macrocyclic Compounds’, ed. R. M. Izatt and J. J. Christensen, Academic Press, New York, 1978.
10. P. D. Beer, in ‘Chemical Sensors’, ed. T. Edmonds, Blackie Glasgow, London, 1988, Chapter 2, p. 17.
11. ‘Host-Guest Chemistry l’, Topics Curr. Chem., 1980, 98.
12. B. Dietrich, in ‘Inclusion Compounds’, Vol. 2, ed. J. L. Atwood, J. E. D. Davies, and D. MacNicol, Academic Press, London, 1984, p. 337.
13. E. Racker, Acc. Chem. Res., 1979, 12, 338.
14. L. Stryer, ‘Biochemistry’, 2nd Edition, Freeman, San Francisco, 1981.
15. S. Shinkai, Pure Appl. Chem., 1987, 59, 425.
16. H. Stetter and W. Frank, Angew. Chem., Int. Ed. Engl. 1976, 15, 686.
17. J. P. Desvergne and H. Bouas-Laurent, J. Chem. Soc, Chem. Commun., 1978, 403.
18. W. Wierenga, B. R. Evans, and J. A. Woltersom, J. Am. Chem. Soc, 1979, 101, 1334.
19. L. A. Frederick, T. M. Fyles, V. A. Malik-Diemer, and D. M. Whitfield, J. Chem. Soc, Chem. Commun., 1980, 1211.
20. L. A. Frederick, T. M. Fyles, N. P. Gurprasad, and D. M. Whitfield, Can. J. Chem., 1981, 59, 1724.
21. T. M. Fyles, V. A. Malik-Diemer, and D. M. Whitfield, Can. J. Chem., 1981, 59, 1734.
22. A. Hriciga and J. M. Lehn, Proc. Natl. Acad. Sci. USA, 1983, 80, 6426.
23. S. Shinkai and O. Manabe, Topics Curr. Chem., 1984,121, 67.
24. S. Shinkai, T. Ogawa, Y. Kusano, and O. Manabe, Chem. Lett., 1980, 283.
25. S. Shinkai, T. Nakaji, T. Ogawa, E. Shigematsu, and O. Manabe, J. Am. Chem. Soc, 1981, 103, 111.
26. J. P. Desvergne, N. Bitit, and H. Bouas-Laurent, J. Chem. Res., 1984, (S) 214
27. D. E. Koshland Jr., in ‘The Enzymes’, Vol. 1, ed. P. Boyer, Academic Press, New York, 1970, p. 341.
28. J. Rebek, Acc. Chem. Res., 1984,17, 258.
29. J. Rebek, J. E. Trend, R. V. Wattley, and S. Chakravorti, J. Am. Chem. Soc, 1979,101,4333.
30. J. Rebek, T. Costello, J. Marshall, R. Wattley, R. C. Gadwood, and K. Onan, J. Am. Chem. Soc, 1985,107, 7481.
31. P. D. Beer and A. S. Rothin, J. Chem. Soc, Chem. Commun., 1988, 52.
32. P. D. Beer and A. S. Rothin, Polyhedron, 1988, 7, 137.
33. P. D. Beer, J. Chem. Soc, Chem. Commun., 1986, 1678.
34. P. D. Beer and C. G. Crane, Polyhedron, 1988, 7, 2649.
35. A. Warshawsky and N. Kahana, J. Am. Chem. Soc, 1982, 104, 2663.
36. P. D. Beer, Aldrichim. Acta, 1989, in press.
37. T. E. Edmonds in ‘Chemical Sensors’, ed. T. E. Edmonds, Blackie Glasgow, London, 1988, Chapter 8, p. 193.
38. P. D. Beer, D. B. Crowe, and B. Main, J. Organomet. Chem., 1989, 375, C35.
39. (a) P. D. Beer and A. D. Keefe, Proceedings of XIII Macrocyclic Conference, Hamburg, September 1988, p. 92
40. (b) P. D. Beer and A. D. Keefe, J. Organomet. Chem., 1989, 375, C40.
41. P. D. Beer and A. D. Keefe, J. Inclusion Phenom., 1987, 5, 499.
42. P. D. Beer, M. G. B. Drew, and A. D. Keefe, J. Organomet. Chem., 1988, 353, CIO.
43. P. D. Beer, M. G. B. Drew, and A. D. Keefe, J. Organomet. Chem., 1989, in press.
44. P. D. Beer and E. L. Tite, Tetrahedron Lett., 1988, 2349.
45. P. D. Beer, M. G. B. Drew, A. Ibbotson, and E. L. Tite, J. Chem. Soc, Chem. Commun., 1988, 1498.
46. P. D. Beer, A. D. Keefe, and E. L. Tite, J. Coord. Chem., 1988,18, 213.
47. R. E. Wolf, and S. R. Cooper, J. Am. Chem. Soc, 1984, 106, 4646.
48. H. Bock, B. Hierholzer, F. Vogtle, and G. Hollman, Angew. Chem., Int. Ed. Engl., 1984, 23, 57.
49. L. Echegoyen, D. A. Gustowski, V. J. Gatto, and G. W. Gokel, J. Chem. Soc, Chem. Commun., 1986. 220.
50. D. A. Gustowski, M. Delgado, V. J. Gatto, L. Echegoyen, and G. W. Gokel, J. Am. Chem. Soc, 1986, 108, 7553.
51. K. Maruyama, H. Sohmiya, and H. Tsukube, J. Chem. Soc, Perkin Trans. 1, 1986, 2069.
52. F. Dietl, G. Gierer, and A. Merz, Synthesis, 1986, 626.
53. K. Hayakawa, K. Kido, and K. Kanematsu, J. Chem. Soc, Perkin Trans. I, 1988, 511.
54. H. Togo, K. Hashimoto, K. Morihashi, and O. Kikuchi, Bull. Soc Jpn., 1988, 61, 3026.
55. A. Kaifer, L. Echegoyen, D. A. Gustowski, D. M. Goli, and G. W. Gokel, J. Am. Chem. Soc, 1983, 105, 7168.
56. A. Kaifer, D. A. Gustowski, L. Echegoyen, V. J. Gatto, R. A. Schultz, T. P. Cleary, C. R. Morgan, D. M. Goli, A. M. Rios, and G. W. Gokel, J. Am. Chem. Soc, 1985, 107, 1958.
57. S. R. Miller, D. A. Gustowski, Z. C. Chen, G. W. Gokel, L. Echegoyen, and A. E. Kaifer, Anal. Chem., 1988, 60, 2021.
58. Although other organic redox active moieties such as flavin and NADH have been recently incorporated into macrocyclic structures their electrochemical properties have not been reported. See, for example: (a) S. Shinkai, Y. Ishikawa, H. Shinkai, T. Tsuno, H. Makishima, K. Ueda, and O. Manabe, J. Am. Chem. Soc, 1984, 106, 1801
59. (h) J. D. De Vries and R. M. Kellog, J. Chem. Soc, 1979, 101, 2759
60. (c) E. Seward and F. Diederich, Tetrahedron Lett., 1987, 28, 5111.
61. P. D. Beer, N. Al-Obaidi, J. P. Bright, C. J. Jones, J. A. McCleverty, and S. S. Salam, J. Chem. Soc, Chem. Commun., 1986, 239.
62. P. D. Beer, C. J. Jones, J. A. McCleverty, and S. S. Salam, J. Inclusion Phenom., 1987, 5, 504.
63. P. D. Beer, T. A. Hamor, N. Al-Obaidi, C. J. Jones, and J. A. McCleverty, unpublished results.
64. T. Saji, Chem. Lett., 1986, 275.
65. T. Saji and I. Kinoshita, J. Chem. Soc., Chem. Commun., 1986, 716.
66. L. E. Echegoyen, H. K. Yoo, V. J. Gatto, G. W. Gokel, and L. Echegoyen, J. Am. Chem. Soc, 1989, 111,2440.
67. K. Kimura, H. Sakamoto, Y. Koseki, and T. Shono, Chem. Lett., 1985, 1241.
68. M. Bourgoin, K. H. Wong, J. Y. Hui, and J. Smid, J. Am. Chem. Soc, 1975, 97, 3462.
69. K. Kikukawa, G. X. He, A. Abe, T. Goto, R. Arata, T. Ikeda, F. Wada, and T. Matsuda, J. Chem. Soc, Perkin Trans. 2, 1987, 135.
70. P. D. Beer, J. Chem. Soc, Chem. Commun., 1985, 1115.
71. P. D. Beer, J. Organomet. Chem., 1985, 297, 313.
72. P. D. Beer, H. Sikanyika, A. M. Z. Slawin, and D. J. Williams, Polyhedron, 1989, 8, 879.
73. P. D. Beer and H. Sikanyika, J. Organomet. Chem., unpublished results.
74. P. D. Beer and A. D. Keefe, J. Organomet. Chem., 1986, 306, CIO.
75. R. A. W. Johnstone and M. E. Rose, J. Chem. Soc, Chem. Commun., 1983, 1268.
76. P. D. Beer, H. Sikanyika, C. Blackburn, and J. F. McAleer, J. Organomet. Chem., 1988, 350, CI5.
77. M. P. Andrews, C. Blackburn, J. F. McAleer, and V. D. Patel, J. Chem. Soc., Chem. Commun., 1987, 1122.
78. P. D. Beer, H. Sikanyika, C. Blackburn, and J. F. McAleer, Inorg. Chem., in press.
79. P. D. Beer, H. Sikanyika, C. Blackburn, J. F. McAleer, and M. G. B. Drew, J. Organomet. Chem., 1988, 356, C19.
80. P. J. Hammond, A. P. Bell, and C. D. Hall, J. Chem. Soc., Perkin Trans. 1, 1983, 707.
81. P. D. Beer, P. J. Hammond, and C. D. Hall, J. Chem. Soc, Chem. Commun., 1983, 1161.
82. P. D. Beer. J. Elliot, P. J. Hammond, C. Dudman, and C. D. Hall, J. Organomet. Chem., 1984, 263, C37.
83. P. D. Beer, P. J. Hammond, C. Dudman, I. P. Danks, C. D. Hall, J. Kynchala, and M. C. Grossel, J. Organomet. Chem., 1986, 306, 367.
84. P. D. Beer, C. D. Bush, and T. A. Hamor, J. Organomet. Chem., 1988, 339, 133.
85. M. C. Grossel, M. R. Goldspink, J. P. Kynchala, A. K. Cheetham, and J. A. Hriljac, J. Organomet. Chem., 1988, 352, C13.
86. P. D. Beer, C. G. Crane, A. D. Keefe, and A. R. Whyman, J. Organomet. Chem., 1986, 314, C9.
87. P. D. Beer and A. D. Keefe, unpublished results.
88. C. D. Hall, N. W. Sharpe, I. P. Danks, and Y. P. Sang, J. Chem. Soc, Chem. Commun., 1989, 419.
89. E. Fu, M. L. H. Green, V. J. Lowe, and S. R. Marder, Organomet. Chem., 1988, 341, C39.
90. E. Fu, J. Granell, M. L. H. Green, V. J. Lowe, S. R. Marder, G. C. Saunders, and M. Tuddenham, J. Organomet. Chem., 1988, 355, 205.
91. E. Graf and J. M. Lehn, J. Am. Chem. Soc, 1975, 97, 5022.
92. E. Graf and J. M. Lehn, Helv. Chim. Acta, 1981, 64, 1040.
93. J. M. Lehn, Pure Appl. Chem., 1978, 50, 871.
94. J. J. R. Frausto da Silva and R. J. P. Williams, Struct. Bonding (Berlin), 1976, 29, 67.
95. M. Newcomb, J. H. Horner, and M. T. Blanda, J. Am. Chem. Soc, 1987, 109, 7878.
96. J. P. West and B. Zacharie, J. Am. Chem. Soc, 1987,109, 4714.
97. M. E. Jung and H. Xia, Tetrahedron Lett., 1988, 29, 297.
98. F. P. Schmidtchen, Angew. Chem., Int. Ed. Engl., 1977, 16, 720.
99. C. H. Park and H. E. Simmons, J. Am. Chem. Soc., 1968, 90, 2431.
100. J. M. Lehn, E. Sonveaux, and A. K. Willard, J. Am. Chem. Soc, 1978,100, 4914.
101. J. M. Lehn and D. Heyer, Tetrahedron Lett., 1986, 27, 5869.
102. M. W. Hosseini and J. M. Lehn, Helu. Chim. Acta, 1986, 69, 587.
103. D. J. Cram, Science, 1983, 219, 1177.
104. D. J. Cram, Angew. Chem., Int. Ed. Engl., 1986, 25, 1039.
105. F. Diederich, Angew. Chem., Int. Ed. Engl., 1988, 27, 362.
106. J. Franke and F. Vogtle, Top. Curr. Chem., 1986,132, 135.
107. A. Ben-Naim, ‘Hydrophobic Interactions,’ Plenum Press, New York, 1980.
108. Note added in proof. We have recently discovered that the novel ferrocenyl ionophore (44) selectively complexes, electrochemically recognizes, and responds to the potassium guest ion in the presence of equimolar amounts of sodium and magnesium ions (reference 104).
109. Simple ferrocene derivatives have recently been shown to exhibit non-linear optical behaviour, see for example: M. L. H. Green, S. R. Marder, M. E. Thompson, J. A. Bandy, D. Bloor, P. V. Kolinsky, and R. J. Jones, Nature, 1987, 330, 360
110. M. L. H. Green, J. Qin, D. O’Hare, H. E. Bunting, M. E. Thompson, S. R. Marder and K. Chatakondu, Pure Appl. Chem., 1989, 61, 817.
111. P. D. Beer, H. Sikanyika, C. Blackburn, and J. F. McAleer, J. Chem. Soc, Chem. Commun., 1989, in press.