Synthesis of porphyrin dimers fused with a benzene unit

Chemistry - A European Journal

Volumn 13, Issue 20, 2007, Pages 5773-5784

  Uno, Hidemitsu ^a,b   Nakamoto, Ken Ichi ^a   Kuroki, Kenji ^a   Fujimoto, Akiko ^a,b   Ono, Noboru ^a  

^a EHIME UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Conjugation; Dimerization; Porphyrinoids; RetroDiels Alder reaction; Stacking interactions

Indexed keywords

PORPHYRINOIDS; RETRODIELS-ALDER REACTION; STACKING INTERACTIONS;

BENZENE; PORPHYRINS; PYROLYSIS; SYNTHESIS (CHEMICAL);

DIMERS;

EID: 34547196792     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601644     Document Type: Article

References (45)

1. a) M. Berliocchi, M. Manenti, A. Bolognesi, A. Di Carlo, P. Ligli, R. Paolesse, F. Mandoy, C. Di Natale, E. Proiette, G. Petrocco, A. D'Amico, Semicond. Sci. Technol. 2004, 19, S354-S356;
2. b) C. D. Dimitrakopoulos, D. J. Mascaro, IBM J. Res. Dev. 2001, 45, 11-30;
3. c) N. R. Armstrong, J. Porphyrins and Phthalocyanines 2000, 4, 414-417;
4. d) P. Alivisatos, P. F. Barbara, A. W. Castleman, J. Chang, D. A. Dixon, M. L. Klein, G. L. McLendon, J. S. Miller, M. A. Ratner, P. J. Rossky, S. I. Stupp, M. E. Thompson, Adv. Mater. 1998, 10, 1297-1336, and references therein.
5. a) P. Thordarson, A. Marquis, M. J. Crossley, Org. Biomol. Chem. 2003, 1, 1216-1225;
6. b) M. J. Crossley, P. Thordarson, Angew. Chem. 2002, 114, 1785-1788;
7. Angew. Chem. Int. Ed. 2002, 41, 1709-1712;
8. J. Crossley, L. A. Johnston, Chem. Commun. 2002, 1122-1123;
9. c) R. Beavington, P. L. Burn, J. Chem. Soc. Perkin Trans. 1 2000, 1231-1240;
10. d) R. Beavington, P. L. Burn, J. Chem. Soc. Perkin Trans. 1 2000, 605-609;
11. e) J. R. Reimers, TX. Lu, M. J. Crossley, N. S. Hush, Chem. Phys. Lett. 1996, 256, 353-359;
12. f) M. J. Crossley, P. L. Burn, J. Chem. Soc. Chem. Commun. 1987, 39-40.
13. a) R. Paolesse, L. Jaquinod, F. Della Sala, D. J. Nurco, L. Prodi, M. Montalti, C. Di Natale, A. D'Amico, A. Di Carlo, P. Lugli, K. M. Smith, J. Am. Chem. Soc. 2000, 122, 11 295-11 302;
14. b) L. Jaquinod, O. Siri, R. G. Khoury, K. M. Smith, Chem. Commun. 1998, 1261-1262;
15. c) N. Kobayashi, M. Numao, R. Kondo, S. Nakajima, T. Osa, Inorg. Chem. 1991, 30, 2241-2244.
16. M. G. H. Vicente, M. T. Cancilla, C. B. Lebrilla, K. M. Smith, Chem. Commun. 1998, 2355-2356.
17. a) A. Tsuda, A. Osuka, Science 2001, 293, 79-82;
18. b) A. Tsuda, H. Furuta, A. Osuka, J. Am. Chem. Soc. 2001, 123, 10304-10321;
19. c) N. Aratani, A. Tsuda, A. Osuka, Synlett 2001, 1663-1674;
20. d) A. Tsuda, A. Nakano, H. Furuta, H. Yanomochi, A. Osuka, Angew. Chem. 2000, 112, 572-575;
21. Angew. Chem. Int. Ed. 2000, 39, 558-561;
22. e) K. Sugiura, T. Matsumoto, S. Ohkouchi, Y. Naitoh, T. Kawai, Y. Takai, K. Ushiroda, K. Sakata, Chem. Commun. 1999, 1957-1958.
23. a) T. Okujima, N. Komobuchi, Y. Shimizu, H. Uno, N. Ono, Tetrahedron Lett. 2004, 45, 5461-5464;
24. b) N. Ono, K. Kuroki, E. Watanabe, N. Ochi, H. Uno, Heterocycles 2004, 62, 365-373;
25. c) H. Uno, T. Ishikawa, T. Hoshi, N. Ono, Tetrahedron Lett. 2003, 44, 5163-5165, and references therein.
26. S. Ito, K. Nakamoto, H. Uno, T. Murashima, N. Ono, Chem. Commun. 2001, 2696-2697.
27. H. Uno, A. Masumoto, N. Ono, J. Am. Chem. Soc. 2003, 125, 12082-12083.
28. a) H. Uno, S. Ito, M. Wada, H. Watanabe, M. Nagai, A. Hayashi, T. Murashima, N. Ono, J. Chem. Soc. Perkin Trans. 1 2000, 4347-4355;
29. b) Y. Abel, F.-P. Montforts, Tetrahedron Lett. 1997, 38, 1745-1748.
30. a) A. Boudif, M. Momenteau, J. Chem. Soc. Chem. Commun. 1994, 2069-2070;
31. b) A. Boudif, M. Momenteau, J. Chem. Soc. Perkin Trans. 1 1996, 1235-1242;
32. c) J. L. Sessler, J. W. Genge, A. Urbach, P. Sanson, Synlett 1996, 187-188;
33. d) T. D. Lash, P. Chandrasekar, A. T. Osuma, S. T. Chaney, J. D. Spence, J. Org. Chem. 1998, 63, 8455-8469.
34. K. M. Smith, in The Porphyrin Handbook, Vol. 1 (Eds.: M. K. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 1999, p. 2-44.
35. a) J. L. Sessler, M. R. Johnson, V. Lynch, J. Org. Chem. 1987, 52, 4394-4397;
36. b) S. V. Shevchuk, J. M. Davis, J. L. Sessler, Tetrahedron Lett. 2001, 42, 2447-2450.
37. J. L. Sessler, A. Mozaffari, M. R. Martin, Org. Synth. 1998, 9, 242-249.
38. J. B. Paine III, D. Dolphin, M. Gouterman, Can. J. Chem. 1978, 56, 1712-1714.
39. "Photochemistry of Porphyrins and Metalloporphyrins": F. R. Hopf, D. G. Whitten, in Porphyrins and Metalloporphyrins (Ed. : K. M. Smith), Elsevier, Amsterdam, 1975, Chapter 16.
40. a) SHELXL-97, program for refinement of crystal structures from diffraction data, University of Göttingen, Göttingen (Germany);
41. G. Scheidrick, T. Schneider, Methods Enzymol. 1997, 277, 319-343;
42. b) PLATON, a multipurpose crystallographic tool, Utrecht Univesity, Utrecht (The Netherlands); A. L. Spek, J. Appl. Crystallogr. 2003, 36, 7-13.
43. J. A. Shelnutt, in The Porphyrin Handbook, Vol. 7 (Eds.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 2000, p. 167-224.
44. G. D. Hatmen, L. M. Weinstock, Org. Synth. 1988, 6, 620-628.
45. S. Ito, N. Ochi, T. Murashima, H. Uno, N. Ono, Heterocycles 2000, 52, 399-411.