Conformational folding induced by π-π interaction in a series of flexible dyads consisting of isomeric mesoporphyrin nitrobenzyl esters

Journal of the Chemical Society. Perkin Transactions 2

Volumn 5, Issue , 1996, Pages 997-1004

  Colominas, Carles ^a   Eixarch, Lisbeth ^b   Fors, Pere ^b   Lang, Kamil ^b,c   Nonell, Santiago ^a   Teixidó, Jordi ^a   Trull, Francesc R ^b  

^a INSTITUT QUÍMIC DE SARRIÀ   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

^c INSTITUTE OF INORGANIC CHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001159779     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/P29960000997     Document Type: Article

References (66)

1. (a) M. R. Wasielewski, Photoinduced Electron Transfer, eds. M. A. Fox and M. Chanon, Elsevier, Amsterdam, 1988, Part A, p. 161;
2. (b) N. Sutin, Electron Transfer in Inorganic, Organic, and Biological Systems, eds. J. R. Bolton, N. Mataga and G. McLendon, Advances in Chemistry Series 228, ACS, Washington, 1991, p. 25.
3. (a) M. R. Wasielewski and M. P. Niemczyk, J. Am. Chem. Soc., 1984, 106, 5043;
4. (b) H. Oevering, M. N. Paddon-Row, M. Heppener, A. M. Oliver, E. Cotsaris, J. W. Verhoeven and N. S. Hush, J. Am. Chem. Soc., 1987, 109, 3258.
5. A. Osuka, K. Maruyama and S. Hirayama, Tetrahedron, 1989, 45, 4815
6. (a) Y. Kanda, H. Sato, T. Okada and N. Mataga, Chem. Phys. Lett., 1986, 129, 306;
7. (b) J. Liu, J. A. Schmidt and J. R. Bolton, J. Phys. Chem., 1991, 95, 6924.
8. (a) C. A. Berg-Brennan, D. I. Yoon and J. T. Hupp, J. Am. Chem. Soc., 1993, 115, 2048;
9. (b) L. R. Khundkar, J. W. Perry, J. E. Hanson and P. B. Dervan, J. Am. Chem. Soc., 1994, 116, 9700.
10. (a) R. R. Bucks, T. L. Netzel, I. Fujita and S. G. Boxer, J. Phys. Chem., 1982, 86, 1947;
11. (b) T. A. Moore, D. Gust, P. Mathis, J.-C. Mialocq, C. Chachaty, R. V. Bensasson, E. J. Land, D. Doirit, P. A. Liddell, W. R. Lehman, G. A. Nemeth and A. L. Moore, Nature (London), 1984, 307, 630;
12. (c) D. Gust, T. A. Moore, L. R. Makings, P. A. Liddell, G. A. Nemeth and A. L. Moore, J. Am. Chem. Soc., 1986, 108, 8028;
13. (d) D. Gust, T. A. Moore, P. A. Liddell, G. A. Nemeth, L. R. Makings, A. L. Moore, D. Barrett, P. J. Pessiki, R. V. Bensasson, M. Rougée, C. Chachaty, F. C. De Schriver, M. Van der Anweraer, A. R. Holzwarth and J. S. Connolly, J. Am. Chem. Soc., 1987, 109, 846;
14. (e) R. M. Hermant, P. A. Liddell, S.-Lin, R. G. Alden, H. K. Kang, A. L. Moore, T. A. Moore and D. Gust, J. Am. Chem. Soc., 1993, 115, 2080;
15. (f) J.-C. Chambron, A. Harriman, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1993, 115, 6109;
16. (g) J.-C. Chambron, A. Harriman, V. Heitz and J.-P. Sauvage, J. Am. Chem. Soc., 1993, 115, 7419;
17. (h) S. Prathapan, T. E. Johnson and J. S. Lindsey, J. Am. Chem. Soc., 1993, 115, 7519;
18. (i) J. S. Lindsey, P. A. Brown and D. A. Siesel, Tetrahedron, 1989, 45, 4845;
19. (j) M. R. Wasielewski, Chem. Rev., 1992, 92, 435.
20. (a) A. R. McIntosh, A. Siemiarczuk, J. R. Bolton, M. J. Stillman, T.-F. Ho and A. C. Weedon, J. Am. Chem. Soc., 1983, 105, 7215;
21. (b) A. Siemiarczuk, A. R. McIntosh, T.-F. Ho, M. J. Stillman, K. J. Roach, A. C. Weedon, J. R. Bolton and J. S. Connolly, J. Am. Chem. Soc., 1983, 105, 7224;
22. (c) M. C. González, A. R. McIntosh, J. R. Bolton and A. C. Weedon, J. Chem. Soc., Chem. Commun., 1984, 1138;
23. (d) J. R. Bolton, T.-F. Ho, S. Liauw, A. Siemiarczuk, C. S. K. Wanand and A. C. Weedon, J. Chem. Soc., Chem. Commun., 1985, 559;
24. (e) A. Osuka, S. Morikawa, K. Maruyama, S. Hirayama and T. Minami, J. Chem. Soc., Chem. Commun., 1987, 359;
25. (f) Y. Aoyama, M. Asakawa, Y. Matsui and H. Ogoshi, J. Am. Chem. Soc., 1991, 113, 6233;
26. (g) T. Hayashi, T. Miyahara, N. Hashizume and H. Ogoshi, J. Am. Chem. Soc., 1993, 115, 2049;
27. (h) Y. Kuroda, M. Ito, T. Sera and H. Ogoshi, J. Am. Chem. Soc., 1993, 115, 7003;
28. (i) A. Osuka and K. Maruyama, Tetrahedron, 1989, 45, 4815.
29. (a) H. L. Anderson, C. A. Hunter, N. M. Meah and J. K. M. Sanders, J. Am. Chem. Soc., 1990, 112, 5780;
30. (b) R. J. Harrison, B. Pearce, G. S. Beddard, J. A. Cowan and J. K. M. Sanders, Chem. Phys., 1987, 116, 429.
31. (a) G. R. Seely, J. Phys. Chem., 1972, 76, 172;
32. (b) B. G. Maiya and V. Krishnan, J. Phys. Chem., 1985, 89, 5225 and references therein;
33. (c) G. R. Seely, Tetrahedron, 1989, 45, 4729;
34. (d) F. D'Souza and V. Krishnan, Photochem. Photobiol., 1990, 51, 285;
35. (e) D. Gust, T. A. Moore, D. K. Luttrull, G. R. Seely, E. Bittersmann, R. B. Bensasson, M. Rougée, E. J. Land, F. C. De Schriver and M. Van der Auweraer, Photochem. Photobiol., 1990, 51, 419;
36. (f) F. D'Souza and V. Krishnan, Photochem. Photobiol., 1992, 56, 145;
37. (g) C. Turró, C. K. Chang, G. E. Leroi, R. I. Cukier and D. G. Nocera, J. Am. Chem. Soc., 1992, 114, 4013;
38. (h) M. Sirish and B. G. Maiya, J. Photochem. Photobiol. A, 1994, 77, 189.
39. J. S. Connolly, Photochemical Conversion and Storage of Solar Energy-1982, ed. J. S. Rabani, Weizmann, Jerusalem, 1982, Part A, p. 175.
40. M. A. Fox, Acc. Chem. Res., 1992, 25, 569, and references therein.
41. C. A. Hunter and J. K. M. Sanders, J. Am. Chem. Soc., 1990, 112, 5525.
42. (a) J. A. Riddick and W. B. Bunger, Techniques of Chemistry. Vol. 2. Organic Solvents, ed. A. Weissberger, Wiley Interscience, New York, 1970;
43. (b) D. D. Perrin, D. R. Perrin and W. L. F. Armarego, Purification of Laboratory Chemicals, Pergamon, Oxford, 1980.
44. V. K. Sarin, J. B. H. Kent, J. B. Tam and R. B. Merrifield, Anal. Biochem., 1981, 117, 147.
45. (a) J. M. Ribó, M. L. Sesé and F. R. Trull, React. Polym., 1989, 10, 239;
46. (b) P. Castán, J. M Ribó and F. R. Trull, React. Polym., 1988, 9, 237;
47. (c) S. Nonell, M. L. Sesé, D. O. Mártire, S. E. Braslavsky and F. R. Trull, Photochem. Photobiol., 1991, 53, 185.
48. M. Fontich, P. Fors, M. L. Sesé and F. R. Trull, Eur. Polym. J., 1994, 30, 1143.
49. HYPERCHEM, v. 3.0 1993, Autodesk Inc.
50. SCANTOR 1994, Excel 4.0 macro developed by J. Sedó, Institut Químic de Sarrià, Barcelona.
51. MICROSOFT EXCEL, v. 4.0a 1992, Microsoft Corporation.
52. (a) HYPERCHEM User's Manual; Autodesk Inc. 1992;
53. (b) N. L. Allinger, J. Am. Chem. Soc., 1977, 99, 8127;
54. (c) N. L. Allinger and Y. H. Yoh, QCPE Bull., 1980, 12, 395;
55. (d) O. Burkett and N. L. Allinger, Molecular Mechanics; ACS Monograph Series 177; American Chemical Society, Washington DC, 1982.
56. N. Metropolis and A. W. Rosenbluth, J. Chem. Phys., 1953, 21, 1087.
57. Molecular Advanced Design, v. 2.12 Oxford Molecular X-Pole-Ecole Polytechnique, F-91128 Palaiseau Cédex, France, 1993.
58. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902.
59. AMPAC from MOTECC-91, v. 2.10, D. A. Liotard, E. F. Healy, J. M. Ruiz and M. J. S. Dewar, 1991.
60. (a) M. D. Bentley and M. J. S. Dewar, Tetrahedron Lett., 1967, 50, 5043;
61. (b) G. M. Sanders, M. van Dijk, A. van Veldhuizen and H. C. J. van der Plas, J. Chem. Soc., Chem. Commun., 1986, 1311;
62. (c) G. M. Sanders, M. van Dijk, A. van Veldhuizen, H. C. J. van der Plas, U. Hofstra and T. J. Schaafsma, J. Org. Chem., 1988, 53, 5272;
63. (d) C. A. Hunter, M. N. Meah and J. K. M. Sanders, J. Am. Chem. Soc., 1990, 112, 5773.
64. (a) J. Weiser and H. A. Staab, Angew. Chem., Int. Ed. Engl., 1984, 23, 623;
65. (b) C. Ohm and E. Breitmaier, J. Prakt. Chem., 1994, 376, 530.
66. P. Laszlo, Prog. NMR Spectrosc., 1967, 3, 231.