Coreceptor Molecules. Synthesis of Metalloreceptors Containing Porphyrin Subunits and Formation of Mixed Substrate Supermolecules by Binding of Organic Substrates and of Metal Ions

Journal of the American Chemical Society

Volumn 108, Issue 17, 1986, Pages 5158-5167

  Hamilton, Andrew ^a,b   Lehn, Jean Marie ^a   Sessler, Jonathan L ^a,c  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b PRINCETON UNIVERSITY   (United States)

^c UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845373948     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00277a021     Document Type: Article

References (61)

1. Lehn, J.M. In Biomimetic Chemistry, Yoshida, Z.I., Ise, N., Eds.; Kodansha Ltd.: Tokyo; Elsevier Scientific Publishing Co.: Amsterdam, 1983; pp 163–187.
2. Lehn, J.M. Science 1985, 227, 849–856.
3. Lehn, J.M. In IUPAC Frontiers of Chemistry; Laidler, K. J., Ed.; Pergamon Press: Oxford and New York, 1982; pp 265–272.
4. Lehn, J.M.; Simon, J.; Wagner, J. Angew. Chem. 1973, 85, 622-624.
5. Angew. Chem., Int. Ed. Engl. 1973, 12, 579–580.
6. Dietrich, B.; Lehn, J.M.; Simon, J. Angew. Chem. 1974, 86, 443-444.
7. Angew. Chem., Int. Ed. Engl. 1974, 13, 406–407.
8. Lehn, J.M.; Simon, J.; Moradpour, A. Helv. Chim. Acta 1978, 61, 2407–2418.
9. Breslow, R.; Overman, L.E. J. Am. Chem. Soc. 1970, 92, 1075–1077.
10. Tabushi, I.; Shimizu, N.; Sugimoto, T.; Shokuza, M.; Yamamura, K. J. Am. Chem. Soc. 1977, 99, 7100–7102.
11. Rebek, J., Jr. Acc. Chem. Res. 1984, 17, 258–264.
12. Willner, I.; Goren, Z. J. Chem. Soc., Chem. Commun. 1983, 1469–1470.
13. Hamilton, A.D.; Lehn, J.M.; Sessler, J.L. J. Chem. Soc., Chem. Commun. 1984, 311–313.
14. Chang, C.K. J. Am. Chem. Soc. 1977, 99, 2819–2822.
15. Thanabal, V.; Khrisnan, V. J. Am. Chem. Soc. 1982, 104, 3643–3650.
16. Baldwin, J.E.; Perlmutter, P. Top. Current Chem. 1984, 121, 181–220.
17. Busch, D.H.; Christoph, G.C.; Zimmer, L.L.; Jackels, S.C.; Grzybowski, J.J.; Callahan, R.C.; Kojima, M.; Holter, K.A.; Mocak, J.; Herron, N.; Chavan, M.; Schammel, W.P. J. Am. Chem. Soc. 1981, 103, 5107–5114.
18. Lehn, J.M. Pure Appl. Chem. 1980, 52, 2441–2459.
19. Fischer, H.; Orth, H. Die Chemie des Pyrrols; Akademischer Verlag: Leipzig, 1937.
20. Chang, C.K. J. Am. Chem. Soc. 1977, 99, 2819–2822.
21. Chang, C.K. Adv. Chem. Ser. 1979, 173, 162-177;
22. Ogoshi, H.; Sugimoto, H.; Yoshida, Z. Tetrahedron Lett. 1977, 169–172.
23. Paine, J.B., III In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. IA, Chapter 4.
24. Bullock, E.; Johnson, A.W.; Markahm, E.; Shaw, K.B. J. Chem. Soc. 1958, 1430–1440.
25. Battersby, A.R.; Buckley, D.G.; Hartley, S.G.; Turnbull, M.D. J. Chem. Soc., Chem. Commun. 1976, 879–881.
26. Smith, K. J. Chem. Soc., Perkin Trans. 1, 1972, 1471–1475.
27. Collman, J.P.; Anson, F.C.; Barnes, C.E.; Bencosme, C.S.; Geiger, T.; Evitt, E.R.; Kreh, R.P.; Meier, K.; Pettman, R.B. J. Am. Chem. Soc. 1983, 105, 2694–2699.
28. Collman, J.P.; Denisevich, P.; Konai, Y.; Marrocco, M.; Koval, C.; Anson, F.C. J. Am. Chem. Soc. 1980, 102, 6027–6036.
29. Alberts, A.H.; Annunziata, R.; Lehn, J.M. J. Am. Chem. Soc. 1977, 99, 8502–8504.
30. Lehn, J.M.; Simon, J.; Wagner, J. Angew. Chem. 1973, 85, 621-622.
31. Angew Chem., Int. Ed. Engl. 1973, 12, 578–579.
32. Lehn, J.M.; Simon, J.; Wagner, J. Nouv. J. Chim. 1978, 1, 77–84.
33. White, W.I. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. V, Chapter 7.
34. Gouterman, M. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. IIIA, Chapter 1.
35. Smith, K.M. In Porphyrins and Metalloporphyrins; Smith, K.M., Ed.; Elsevier: Amsterdam, 1975.
36. Spiess, B.; Arnaud-Neu, F.; Schwing-Weill, M. J. Helv. Chim. Acta 1979, 62, 1531–1542.
37. Anderegg, G. Helv. Chim. Acta 1981, 64, 1790–1799.
38. Collman, J.P.; Bencosme, C.S.; Durand, R.R., Jr.; Kreh, R.P.; Anson, F.C. J. Am. Chem. Soc. 1983, 105, 2699–2703.
39. Collman, J.P.; Chong, A.O.; Jameson, G.B.; Oakley, R.T.; Rose, E.; Schmittou, E.R.; Ibers, J.A. J. Am. Chem. Soc. 1981, 103, 516–533.
40. Collman, J.P.; Elliott, C.M.; Halbert, T.R.; Tovrog, B.S. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 18–22.
41. Chang, C.K.; Kuo, M.S.; Wang, C.B. J. Heterocycl. Chem. 1977, 14, 943–945.
42. Chang, C.K. J. Chem. Soc., Chem. Commun. 1977, 800–801.
43. Ward, B.; Wang, C.G.; Chang, C.K. J. Am. Chem. Soc. 1981, 103, 5236–5238.
44. Chang, C.K.; Abdalmuhdi, I. J. Org. Chem. 1983, 48, 5380–5390.
45. Chang, C.K.; Abdalmudi, I. Angew. Chem. 1984, 96, 154-155.
46. Angew. Chem., Int. Ed. Engl. 1984, 23, 164–165.
47. Collman, J.P.; Anson, F.C.; Bencosme, S.; Chong, A.; Collins, T.; Denisevich, P.; Evitt, E.; Geiger, T.; Ibers, J.A.; Jameson, G.; Konai, Y.; Koval, C.; Meier, K.; Oakley, R.; Pettman, R.; Schmittou, E.; Sessler, J.L. In Organic Synthesis Today and Tomorrow (IUPAC); Hutchinson, C.R., Ed.; Pergamon: Oxford, 1981, pp 29–45.
48. Kotzyba-Hibert, F.; Lehn, J.M.; Vierling, P. Tetrahedron Lett. 1980, 941–944.
49. Kotzyba-Hibert, F. Ph D. Thesis, Université Louis Pasteur de Strasbourg, 1983.
50. Kintzinger, J.P.; Kotzyba-Hibert, F.; Lehn, J.M.; Pagelot, A.; Saigo, K. J. Chem. Soc., Chem. Commun. 1981, 833–836.
51. Chevrier, B.; Moras, D., unpublished results.
52. Jones, N.F.; Kumar, A.; Sutherland, I.O. J. Chem. Soc., Chem. Commun. 1981, 990–992.
53. Wijesekera, T.P.; Paine, J.B., III; Dolphin, D.; Eisenstein, F.N.B.; Jones, T. J. Am. Chem. Soc. 1983, 105, 6747–6749.
54. Chang, C.K.; Kuo, M.S. J. Am. Chem. Soc. 1979, 101, 3413–3415.
55. Baldwin, J.E.; Klose, T.; Peters, M. J. Chem. Soc., Chem. Commun. 1976, 881–883.
56. Baldwin, J.E.; Crossley, M.J.; Klose, T.; O’Rear, E.O., III; Peters, M.K. Tetrahedron 1982, 38, 27–39.
57. Momenteau, M.; Mispelter, D.; Loock, B.; Bisagni, E. J. Chem. Soc., Perking Trans. 1, 1983, 189–200.
58. Ogoshi, H.; Sugimoto, H.; Yoshida, Z.I. Tetrahedron Lett. 1976, 4477–4480.
59. Kotzyba-Hibert, F.; Lehn, J.M.; Saigo, K. J. Am. Chem. Soc. 1981, 103, 4266–4268.
60. Pascard, C.; Riche, C.; Cesario, M.; Kotzyba-Hibert, F.; Lehn, J.M. J. Chem. Soc., Chem. Commun. 1982, 557–560.
61. Gubelmann, M.; Lehn, J.M., unpublished results.