Copper(I)-templated synthesis of [2]catenates bearing pendant porphyrins

New Journal of Chemistry

Volumn 22, Issue 5, 1998, Pages 395-409

  Amabilino, David B ^a,b   Sauvage, Jean Pierre ^a  

^a CNRS   (France)

^b INSTITUT DE CIÈNCIA DE MATERIALS DE BARCELONA ICMAB CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000502596     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/a708756j     Document Type: Article

References (61)

1. (a) M. R. Wasielewski, Chem. Rev., 1992, 92, 435;
2. (b) D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198;
3. (c) H. Kurreck and M. Huber, Angew. Chem., Int. Ed. Engl., 1995, 34, 849;
4. (d) D. L. Akins and C. Guo, Adv. Mater., 1994, 6, 512.
5. (a) R. Huber, Chemica Scripta, 1989, 29, 103;
6. (b) H. Michel and J. Deisenhofer, Chemica Scripta, 1989, 29, 205;
7. (c) J. Barber and B. Andersson, Nature (London), 1994, 370, 31.
8. For two stunning recent structures of biological systems exhibiting electron transfer, see: (a) G. McDermott, S. M. Prince, A. A. Freer, A. M. Hawthornthwaite-Lawless, M. Z. Papiz, R. J. Cogdell and N. W. Isaacs, Nature (London), 1995, 374, 517;
9. (b) E. Hofmann, P. M. Wrench, F. P. Sharples, R. G. Hiller, W. Welte and K. Diederichs, Science, 1996, 272, 1788.
10. For selected approaches to synthetic systems incorporating donors and acceptors linked by covalent bonds, see, along with references cited: (a) A. Helms, D. Heiler and G. McLendon, J. Am. Chem. Soc., 1992, 114, 6227;
11. (b) D. Gust, T. A. Moore, A. L. Moore, A. N. Macpherson, A. Lopez, J. M. DeGraziano, I. Gouni, E. Bittersmann, G. R. Seely, F. Gao, R. A. Nieman, X. C. Ma, L. J. Demanche, S.-C. Hung, D. K. Luttrull, S.-J. Lee and P. K. Kerrigan, J. Am. Chem. Soc., 1993, 115, 11141;
12. (c) M. O. Senge, M. G. H. Vicente, K. R. Gerzevske, T. P. Forsyth and K. M. Smith, Inorg. Chem., 1994, 33, 5625;
13. (d) V. S.-Y. Lin, S. G. DiMagno and M. J. Therien, Science, 1994, 264, 1105;
14. (e) A. Osuka, N. Tanabe, S. Kawabata, I. Yamazaki and Y. Nishimura, J. Org. Chem., 1995, 60, 7177;
15. (f) J. Seth, V. Palaniappan, R. W. Wagner, T. E. Johnson, J. S. Lindsey and D. F. Bocian, J. Am. Chem. Soc., 1996, 118, 11194.
16. (a) J. L. Sessler, B. Wang and A. Harriman, J. Am. Chem. Soc., 1995, 117, 704;
17. (b) P. J. F. de Rege, S. A. Williams and M. J. Therien, Science, 1995, 269, 1409;
18. (c) C. A. Hunter and R. K. Hyde, Angew. Chem., Int. Ed. Engl., 1996, 35, 1936.
19. (a) A. M. Brun, S. J. Atherton, A. Harriman, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1992, 114, 4632;
20. (b) A. Harriman, F. Odobel and J.-P. Sauvage, J. Am. Chem. Soc., 1995, 117, 9461;
21. (c) M. J. Crossley, P. L. Burn, S. J. Langford and J. K. Prashar, J. Chem. Soc., Chem. Commun., 1995, 1921;
22. (d) D. B. Amabilino, C. O. Dietrich-Buchecker and J.-P. Sauvage, J. Am. Chem. Soc., 1996, 118, 3285.
23. Comprehensive descriptions of catenanes have been published: (a) G. Schill, Catenanes, Rotaxanes and Knots, Academic Press, New York, 1971;
24. (b) C. Dietrich-Buchecker and J.-P. Sauvage, Bioorg. Chem. Frontiers, 1991, 2, 195;
25. (c) D. B. Amabilino and J. F. Stoddart, Chem. Rev., 1995, 95, 2725.
26. A preliminary report containing some of the work presented in this article has appeared: D. B. Amabilino and J.-P. Sauvage, Chem. Commun., 1996, 2441.
27. (a) P. R. Ashton, M. R. Johnston, J. F. Stoddart, M. S. Tolley and J. W. Wheeler, J. Chem. Soc., Chem. Commun., 1992, 1128;
28. (b) M. J. Gunter and M. R. Johnston, J. Am. Chem. Soc., 1994, 116, 4810;
29. (c) J.-C. Chambron, V. Heitz and J.-P. Sauvage, Bull. Soc. Chim. Fr., 1995, 132, 340;
30. (d) N. Solladié, J.-C. Chambron, C. O. Dietrich-Buchecker and J.-P. Sauvage, Angew. Chem., Int. Ed. Engl., 1996, 35, 906;
31. (e) F. Vögtle, F. Ahuis, S. Baumann and J. Sessler, Liebigs Ann., 1996, 921.
32. (a) J.-C. Chambron, V. Heitz and J.-P. Sauvage, J. Chem. Soc., Chem. Commun., 1992, 1131;
33. (b) J.-C. Chambron, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1993, 115, 12378;
34. (c) J.-C. Chambron, S. Chardon-Noblat, A. Harriman, V. Heitz and J.-P. Sauvage, Pure Appl. Chem., 1993, 65, 2343;
35. (d) J.-C. Chambron, C. Dietrich-Buchecker, V. Heitz, N. Solladié and J.-P. Sauvage, C. R. Seances Acad. Sci. Paris, Série IIb, 1996, 483.
36. J.-C. Chambron, A. Harriman, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1993, 115, 7419.
37. M. Momenteau, F. Le Bras and B. Loock, Tetrahedron Lett., 1994, 35, 3289.
38. C. Dietrich-Buchecker and J.-P. Sauvage, Chem. Rev., 1987, 87, 795.
39. C. Dietrich-Buchecker, J.-P. Sauvage and J.-P. Kintzinger, Tetrahedron Lett., 1983, 24, 5095;
40. (b) C. Dietrich-Buchecker and J.-P. Sauvage, Tetrahedron, 1990, 46, 503.
41. See, for example: Macrocycle Synthesis - A Practical Approach, ed. D. Parker, Oxford University Press, Oxford, 1996.
42. For the synthesis of a closely-related macrocycle, see: J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, Y. Geerts, D. Muscat and K. Müllen, Chem. Commun., 1996, 1243.
43. M. S. Newman and L. F. Lee, J. Org. Chem., 1972, 37, 4468.
44. C.-S. Chan, A. K.-S. Tse and K. S. Chan, J. Org. Chem., 1994, 59, 6084.
45. (a) E. B. Fleischer and A. Laszlo, Inorg. Nucl. Chem. Lett., 1969, 5, 373;
46. (b) M. E. Jamin and R. T. Iwamoto, Inorg. Chim. Acta, 1978, 27, 135.
47. Attempted isolation of any dimeric macrocycle similar to 7 from this reaction was always unsuccessful.
48. Gold(III) porphyrins are known to aggregate with donor porphyrins in aqueous solution, see: (a) H. Segawa, H. Nishino, T. Kamikawa, K. Honda and T. Shimidzu, Chem. Lett., 1989, 1917;
49. (b) H. Segawa, C. Takehara, K. Honda, T. Shimidzu, T. Asahi and N. Mataga, J. Phys. Chem. 1992, 96, 503.
50. Other factors are the poor reactivity of the tosylate group when compared with that of the iodides normally employed in these reactions, as well as the consequent higher temperatures.
51. Dissymmetric catenanes of this type have been prepared successfully using alternative synthetic strategies, see: (a) C. O. Dietrich-Buchecker, C. Hemmert, A.-K. Khémiss and J.-P. Sauvage, J. Am. Chem. Soc., 1990, 112, 8002;
52. (b) D. B. Amabilino, C. O. Dietrich-Buchecker, A. Livoreil, L. Pérez-García, J.-P. Sauvage and J. F. Stoddart, J. Am. Chem. Soc., 1996, 118, 3905;
53. (c) B. Mohr, M. Week, J.-P. Sauvage and R. H. Grubbs, Angew Chem., 1997, 109, 1365.
54. Albrecht-Gary, Z. A.-M. Saad, C. O. Dietrich-Buchecker and J.-P. Sauvage, J. Am. Chem. Soc., 1985, 107, 3205.
55. (a) For a review discussing axial ligation to zinc(n) porphyrins, along with references cited therein, see: J. K. M. Sanders, in Comprehensive Supramolecular Chemistry, eds. J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle and J.-M. Lehn, vol. 9, eds. J.-P. Sauvage and M. W. Hosseini, Elsevier, Oxford, 1996, pp. 131-164;
56. (b) Cyanide ions are known to coordinate through both carbon and nitrogen atoms to metallated phthalocyanines, see: U. Drechsler and M. Hanack, in ref. 25a, pp. 283-311.
57. The topology of catenands is known to enhance kinetics of complexation of metal ions by phenanthroline ligands, see: A.-M. Albrecht-Gary, C. Dietrich-Buchecker, Z. Saad and J.-P. Sauvage, J. Am. Chem. Soc., 1988, 110, 1467.
58. D. B. Amabilino, F. C. De Schryver, G. Hungerford, J.-P. Sauvage and Van der Auweraer, to be published.
59. G. J. Kubas, Inorg. Synth., 1990, 28, 68.
60. I.
61. S. Chardon-Noblat, and J.-P. Sauvage, Tetrahedron, 1991, 47, 5123.