Doubly meso-β-linked diporphyrins from oxidation of 5,10,15-triaryl- substituted Ni(II)- and Pd(II)-porphyrins

Angewandte Chemie - International Edition

Volumn 39, Issue 3, 2000, Pages 558-561

  Tsuda, Akihiko ^a   Nakano, Aiko ^a   Furuta, Hiroyuki ^a   Yamochi, Hideki ^a   Osuka, Atsuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

C C coupling; Porphyrinoids

Indexed keywords

NICKEL; PALLADIUM; PORPHYRIN;

ABSORPTION; ARTICLE; CHEMICAL STRUCTURE; CHLORINATION; CONFORMATION; ELECTROCHEMICAL ANALYSIS; NONHUMAN; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 0034603032     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000204)39:3<558::AID-ANIE558>3.0.CO;2-G     Document Type: Article

References (34)

1. a) M. R. Wasielewski, Chem. Rev. Jpn. 1992, 92, 435;
2. b) D. P. Arnold, G. A. Hearth, J. Am. Chem. Soc. 1993, 115, 121197;
3. c) V. V. Borovkov, G. V. Ponomarev, A. Ishida, T. Kaneda, Y. Sakata, Chem. Lett. 1993, 1409;
4. d) V. S. Y. Lin, S. G. DiMagno, M. J. Therien, Science 1994, 264, 1105;
5. e) R. W. Wagner, J. S. Lindsey, J. Am. Chem. Soc. 1994, 116, 9759;
6. f) B. Jiang, S. W. Yang, D. C. Barbini, W. E. Jones, Jr., Chem. Commun. 1998, 213;
7. g) D. A. Shultz, H. Lee, K. P. Gwaltney, J. Org. Chem. 1998, 63, 7584;
8. h) P. N. Taylor, J. Huuskonen, G. Rumbles, R. T. Aplin, E. Williams, H. L. Anderson, Chem. Commun. 1998, 909:
9. i) J. Wytko, V. Berl, M. McLaughlin, R. R. Tykwinski, M. Schreiber, F. Diederich, C. Boudon, J. P. Gisselbrecht, M. Gross, Helv. Chim. Acta 1998, 81, 1964;
10. j) K. Susumu, T. Shimidzu, K. Tanaka, H. Segawa, Tetrahedron Lett. 1996, 37, 8399;
11. k) R. G. Khoury, L. Jaquinod, K. M. Smith, Chem. Commun. 1997, 1057;
12. l) L. Ruhlmann, S. Lobstein, M. Gross, A. Giraudeau, J. Org. Chem. 1999, 64, 1352;
13. m) O. Mongin, A. Gossauer, Tetrahedron 1997, 53, 6835;
14. n) M.O. Senge, X. Feng, Tetrahedron Lett. 1999, 40, 4165.
15. a) M. J. Crossley, P.L. Burn, J. Chem. Soc. Chem. Commun. 1987, 39;
16. b) M. J. Crossley, P. L. Burn, Chem. Commun. 1991, 1569;
17. c) M. J. Crossley, L. J. Govenlock, J. K. Prasker, Chem. Commun. 1995, 2379.
18. a) L. Jaquinod, O. Siri, R. G. Khoury, K. M. Smith, Chem. Commun. 1998, 1261;
19. b) M. G. H. Vicente, M. T. Cancilla, C. B. Lebrilla, K. M. Smith, Chem. Commun. 1998, 2355.
20. A. Osuka, H. Shimidzu, Angew Chem. 1997, 109, 93; Angew. Chem. Int. Ed. Engl. 1997, 36, 135.
21. A. Osuka, H. Shimidzu, Angew Chem. 1997, 109, 93; Angew. Chem. Int. Ed. Engl. 1997, 36, 135.
22. T. Ogawa, Y. Nishimoto, N. Yoshida, N. Ono, A. Osuka, Chem. Commun. 1998, 337.
23. T. Ogawa, Y. Nishimoto, N. Yoshida, N. Ono, A. Osuka, Angew Chem. 1999, 111, 140: Angew. Chem. Int. Ed. 1999, 38, 176.
24. T. Ogawa, Y. Nishimoto, N. Yoshida, N. Ono, A. Osuka, Angew Chem. 1999, 111, 140: Angew. Chem. Int. Ed. 1999, 38, 176.
25. P. J. Spellane, M. Gouterman, A. Antipas, S. Kim, Y. C. Liu, Inorg. Chem. 1980, 19, 386.
26. MALDI-TOF MS analysis revealed the molecular weights of 2260 (monochlorinated triporphyrins) and 2295 (dichlorinated triporphyrins) for the triporphyrin fraction, and those of 2970 (tetraporphyrins), 3000 (monochlorinaled tetraporphyrins), and 3032 (dichlorinated tetraporphyrins) for the tetraporphyrin fraction. The triporphyrin and tetraporphyrin fractions show the absorption bands at 405, 555, 765, and 899 nm and 407, 554, 776, and 910 nm. respectively.
27. N. Yoshida, H. Shimidzu, A. Osuka, Chem. Lett. 1998, 55.
28. Mixture of meso-chlorinated and -brominated porphyrins in a ratio of 1:1.
29. 2 with all observed reflections. All non-hydrogen atoms were refined anisotropically, and hydrogen atoms were added to calculated positions. Programs used: structure determination with SIR92 and refined with teXane for Windows. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-133210. 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).
30. In this case, meso-chlorinated product was not obtained. A possible mechanism for the meso-bromination may be bromine-atom abstraction by a metalloporphyrin meso-radical, since the only available bromine source is BAHA.
31. M. Terazima, H. Shimidzu, A. Osuka, J. Appl. Phys. 1997, 81, 2946.
32. J. R. Reimers, T. X. Lü, M. J. Crossley, N. S. Hush, Chem. Phys. Lett. 1996, 256, 353.
33. 3.
34. 4: K. Sugiura, T. Matsumoto, S. Ohkouchi, Y. Naitoh, T. Kawai, Y. Takai, K. Ushiroda, Y. Sakata, Chem. Commun. 1999, 1957.