Facile synthesis of β-derivatized porphyrins - Structural characterization of a β - β-bis-porphyrin

Angewandte Chemie - International Edition

Volumn 39, Issue 6, 2000, Pages 1066-1068

  Deng, Yongqi ^a   Chang, C K ^b   Nocera, Daniel G ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

Boronates; Cross coupling; Exciton coupling; Porphyrinoids

Indexed keywords

PORPHYRIN DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PORPHYRIN METABOLISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034677692     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000317)39:6<1066::AID-ANIE1066>3.0.CO;2-G     Document Type: Article

References (48)

1. M. R. Wasielewski, Chem. Rev. 1992, 92, 435.
2. a) J. L., Sessler, M. R. Johnson, T. Y. Liu, S. E. Greager, J. Am. Chem. Soc. 1988, 110, 369;
3. b) J. L. Sessler, V. L. Capuano, A. Harriman, J. Am. Chem. Soc. 1993, 115, 4618.
4. a) A. Helms, D. Heiler, G. McLendon, J. Am. Chem. Soc. 1991, 113, 4325;
5. b) A. Helms, D. Heiler, G. McLendon, J. Am. Chem. Soc. 1992, 114, 6227.
6. a) A. Osuka, K. Maruyama, N. Mataga, T. Asahi, I. Yamazaki, N. Tami, J. Am. Chem. Soc. 1990, 112, 4958;
7. b) A. Osuka, S. Marumo, N. Mataga, S. Taniguchi, T. Okada, I. Yamazaki, Y. Nishimura, T. Ohno, K. Nozaki, J. Am. Chem. Soc. 1996, 118, 155.
8. A. Harriman, J. P. Sauvage, Chem. Soc. Rev. 1996, 25, 41.
9. R. Kumble, S. Palese, V. S.-Y. Lin, M. J. Therien, R. M. Hochstrasser, J. Am. Chem. Soc. 1998, 120, 11 489.
10. a) R. W. Wagner, J. S. Lindsey, J. Am. Chem. Soc. 1994, 116, 9759;
11. b) J.-S. Hsiao, B. P. Krueger, R. W. Wagner, T. E. Johnson, J. K. Delaney, D. C. Mauzerall, G. R. Fleming, J. S. Lindsey, D. F. Bocian, R. J. Donohoe, J. Am. Chem. Soc. 1996, 11 181;
12. c) P. G. Van Patten, A. P. Shreve, J. S. Lindsey, R. J. Donohoe, J. Phys. Chem. B 1998, 102, 4209;
13. d) S. I. Yang, J. Seth, T. Balasubramanian, D. Kim, J. S. Lindsey, D. Holten, D. F. Bocian, J. Am. Chem. Soc. 1999, 121, 4008.
14. V. S.-Y. Lin, S. G. Dimagno, M. J. Therien, Science 1994, 264, 1105.
15. X. Zhou, K. S. Chang, J. Org. Chem. 1998, 63, 99.
16. D. Gust, T. A. Moore, A. L. Moore, Acc. Chem. Res. 1993, 26, 198.
17. N. S. Hush, J. R. Reimers, L. E. Hall, L. A. Johnston, M. J. Crossley, Ann. N. Y. Acad. Sci. 1998, 852, 1.
18. a) C. C. Mak, D. Pomeranc, M. Montalti, L. Prodi, J. K. M. Sanders, Chem. Commun. 1999, 1083;
19. b) S. L. Darling, C. C. Mak, N. Bampos, N. Feeder, S. J. Teat, J. K. M. Sanders, New. J. Chem. 1999, 23, 359;
20. c) S. Anderson, H. L. Anderson, A. Bashall, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1995, 107, 1996; Angew. Chem. Int. Ed. Engl. 1995, 14, 1096.
21. c) S. Anderson, H. L. Anderson, A. Bashall, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1995, 107, 1996; Angew. Chem. Int. Ed. Engl. 1995, 14, 1096.
22. K. Susumu, T. Shimidzu, K. Tanaka, H. Segawa, Tetrahedron Lett. 1996, 37, 8399.
23. R. G. Khoury, L. Jaquinod, K. M. Smith, Chem. Commun. 1997, 1057.
24. M. O. Senge, X. D. Feng, Tetrahedron Lett. 1999, 40, 4165.
25. a) A. Osuka, H. Shimidzu, Angew. Chem. 1997, 109, 93; Angew. Chem. Int. Ed. Engl. 1997, 36, 135;
26. a) A. Osuka, H. Shimidzu, Angew. Chem. 1997, 109, 93; Angew. Chem. Int. Ed. Engl. 1997, 36, 135;
27. b) T. Ogawa, Y. Nishimoto, N. Yoshida, N. Ono, A. Osuka, Angew. Chem. 1999, 111, 140; Angew. Chem. Int. Ed. 1999, 38, 176.
28. b) T. Ogawa, Y. Nishimoto, N. Yoshida, N. Ono, A. Osuka, Angew. Chem. 1999, 111, 140; Angew. Chem. Int. Ed. 1999, 38, 176.
29. J. B. Paine, III, D. Dolphin, Can. J. Chem. 1978, 56, 1710.
30. T. Ishiyama, M. Murata, N. Miyaura, J. Org. Chem. 1995, 60, 7508.
31. Compound 1 was obtained as a minor product in the standard etioporphyrin I synthesis. Apparently an ethyl group was replaced by bromine during the formation of the dipyrrylmethene precursor under harsh bromination conditions. Being less basic, 1 can be separated from etioporphyrin by acid extractions, for example, 20 g of 1 from 3 kg of etioporphyrin. Other Heck reactions with homologous β-bromoporphyrins have been reported, see H. Ali, J. E. van Lier, Tetrahedron 1994, 50, 11 933.
32. M. Murata, S. Watanabe, Y. Masuda, J. Org. Chem. 1997, 62, 6458.
33. 2Zn: calcd: 638.27712; found: 638.27705.
34. A. G. Hyslop, M. A. Kellett, P. M. Iovine, M. J. Therien, J. Am. Chem. Soc. 1998, 120, 12676.
35. 8Zn: calcd: C 70.24, H 6.09, N 10.92; found: C 70.32, H 6.12, N 11.03.
36. 2 = 0.1983. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-133672. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam. ac.uk).
37. W. R. Scheidt, M. E. Kastner, K. Hatano, Inorg. Chem. 1978, 3, 706.
38. K. M. Barkigia, M. D. Berber, J. Fajer, C. J. Medforth, M. W. Renner, K. M. Smith, J. Am. Chem. Soc. 1990, 112, 8851.
39. X. Zhou, Z. Y. Zhou, T. C. W. Mak, K. S. Chan, J. Chem. Soc. Perkin Trans. 1 1994, 2519.
40. B. Krattinger, D. J. Nurco, K. M. Smith, Chem. Commun. 1998, 757.
41. x should red-shift about the unperturbed B band. In 3a, both transitions red-shift relative to the B hand of the monomer. The same situation occurs for the meso - β and the meso - meso bis-porphyrins of ref. [16b)]. These red shifts indicate that the exciton coupling in porphyrins linked by a single bond is augmented by other factors; one likely factor is electronic coupling between porphyrin subunits across the C-C bond.
42. 4OZn: calcd: 616.21806; found: 616.21786.
43. S. G. DiMagno, V. S.-Y. Lin, M. J. Therien, J. Org. Chem. 1993, 58, 5983.
44. X. Zhou, M. K. Tse, T. S. M. Wan, K. S. Chan, J. Org. Chem. 1996, 61, 3590.
45. a) Y. Q. Deng, J. A. Roberts, S. M. Peng, C. K. Chang, D. G. Nocera, Angew. Chem. 1997, 109, 2216; Angew. Chem. Int. Ed. Engl. 1997, 36, 2124;
46. a) Y. Q. Deng, J. A. Roberts, S. M. Peng, C. K. Chang, D. G. Nocera, Angew. Chem. 1997, 109, 2216; Angew. Chem. Int. Ed. Engl. 1997, 36, 2124;
47. b)C. Turró, C. K. Chang, G. E. Leroi, R. I. Cukier, D. G. Nocera, J. Am. Chem. Soc. 1992, 114, 4013.
48. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.