Spin alignment of orthogonal π-radicals of directly meso-linked porphyrin arrays

Chemical Communications

Volumn , Issue 24, 2002, Pages 3032-3033

  Segawa, Hiroshi ^a   Machida, Daiki ^a   Senshu, Yutaka ^a   Nakazaki, Jotaro ^a   Hirakawa, Kazutaka ^a   Wu, Feipeng ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN DERIVATIVE; RADICAL; ZINC DERIVATIVE;

ARTICLE; CHEMICAL INTERACTION; CYCLIC POTENTIOMETRY; ELECTRON SPIN RESONANCE; OXIDATION REDUCTION REACTION; STEREOSPECIFICITY; TEMPERATURE DEPENDENCE;

EID: 0036923082     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b209172k     Document Type: Article

References (34)

1. H. Iwamura and N. Koga, Acc. Chem. Res., 1993, 26, 346-351; J. S. Miller, Angew. Chem., Int. Ed. Engl., 1994, 33, 385-415; A. Rajca, Chem. Rev., 1994, 94, 871-893; J. S. Miller and A. J. Epstein, Chem. Commun., 1998, 1319-1325.
2. H. Iwamura and N. Koga, Acc. Chem. Res., 1993, 26, 346-351; J. S. Miller, Angew. Chem., Int. Ed. Engl., 1994, 33, 385-415; A. Rajca, Chem. Rev., 1994, 94, 871-893; J. S. Miller and A. J. Epstein, Chem. Commun., 1998, 1319-1325.
3. H. Iwamura and N. Koga, Acc. Chem. Res., 1993, 26, 346-351; J. S. Miller, Angew. Chem., Int. Ed. Engl., 1994, 33, 385-415; A. Rajca, Chem. Rev., 1994, 94, 871-893; J. S. Miller and A. J. Epstein, Chem. Commun., 1998, 1319-1325.
4. H. Iwamura and N. Koga, Acc. Chem. Res., 1993, 26, 346-351; J. S. Miller, Angew. Chem., Int. Ed. Engl., 1994, 33, 385-415; A. Rajca, Chem. Rev., 1994, 94, 871-893; J. S. Miller and A. J. Epstein, Chem. Commun., 1998, 1319-1325.
5. Magnetic Properties of Organic Materials, ed. P. M. Lahti, Marcel Dekker, New York, 1999; Molecular Magnetism - New Magnetic Materials, ed. K. Itoh and M. Kinoshita, Kodansha - Gordon & Breach, Tokyo, 2000.
6. Magnetic Properties of Organic Materials, ed. P. M. Lahti, Marcel Dekker, New York, 1999; Molecular Magnetism - New Magnetic Materials, ed. K. Itoh and M. Kinoshita, Kodansha - Gordon & Breach, Tokyo, 2000.
7. M. M. Wienk and R. A. J. Janssen, J. Am. Chem. Soc., 1997, 119, 4492-4501; R. J. Bushby and D. Gooding, J. Chem. Soc., Perkin Trans. 2, 1998, 1069-1075; J. Sedó, N. Ventosa, D. Ruiz-Molina, M. Mas, E. Molins, C. Rovira and J. Veciana, Angew. Chem., Int. Ed., 1998, 37, 330-333; H. Nishide, T. Ozawa, M. Miyasaka and E. Tsuchida, J. Am. Chem. Soc., 2001, 123, 5942-5946; A. Rajca, J. Wongsriratanakul and S. Rajca, Science, 2001, 294, 1503-1505.
8. M. M. Wienk and R. A. J. Janssen, J. Am. Chem. Soc., 1997, 119, 4492-4501; R. J. Bushby and D. Gooding, J. Chem. Soc., Perkin Trans. 2, 1998, 1069-1075; J. Sedó, N. Ventosa, D. Ruiz-Molina, M. Mas, E. Molins, C. Rovira and J. Veciana, Angew. Chem., Int. Ed., 1998, 37, 330-333; H. Nishide, T. Ozawa, M. Miyasaka and E. Tsuchida, J. Am. Chem. Soc., 2001, 123, 5942-5946; A. Rajca, J. Wongsriratanakul and S. Rajca, Science, 2001, 294, 1503-1505.
9. M. M. Wienk and R. A. J. Janssen, J. Am. Chem. Soc., 1997, 119, 4492-4501; R. J. Bushby and D. Gooding, J. Chem. Soc., Perkin Trans. 2, 1998, 1069-1075; J. Sedó, N. Ventosa, D. Ruiz-Molina, M. Mas, E. Molins, C. Rovira and J. Veciana, Angew. Chem., Int. Ed., 1998, 37, 330-333; H. Nishide, T. Ozawa, M. Miyasaka and E. Tsuchida, J. Am. Chem. Soc., 2001, 123, 5942-5946; A. Rajca, J. Wongsriratanakul and S. Rajca, Science, 2001, 294, 1503-1505.
10. M. M. Wienk and R. A. J. Janssen, J. Am. Chem. Soc., 1997, 119, 4492-4501; R. J. Bushby and D. Gooding, J. Chem. Soc., Perkin Trans. 2, 1998, 1069-1075; J. Sedó, N. Ventosa, D. Ruiz-Molina, M. Mas, E. Molins, C. Rovira and J. Veciana, Angew. Chem., Int. Ed., 1998, 37, 330-333; H. Nishide, T. Ozawa, M. Miyasaka and E. Tsuchida, J. Am. Chem. Soc., 2001, 123, 5942-5946; A. Rajca, J. Wongsriratanakul and S. Rajca, Science, 2001, 294, 1503-1505.
11. M. M. Wienk and R. A. J. Janssen, J. Am. Chem. Soc., 1997, 119, 4492-4501; R. J. Bushby and D. Gooding, J. Chem. Soc., Perkin Trans. 2, 1998, 1069-1075; J. Sedó, N. Ventosa, D. Ruiz-Molina, M. Mas, E. Molins, C. Rovira and J. Veciana, Angew. Chem., Int. Ed., 1998, 37, 330-333; H. Nishide, T. Ozawa, M. Miyasaka and E. Tsuchida, J. Am. Chem. Soc., 2001, 123, 5942-5946; A. Rajca, J. Wongsriratanakul and S. Rajca, Science, 2001, 294, 1503-1505.
12. K. Matsuda and M. Irie, J. Am. Chem. Soc., 2000, 122, 7195-7201; K. Matsuda and M. Irie, J. Am. Chem. Soc., 2000, 122, 8309-8310.
13. K. Matsuda and M. Irie, J. Am. Chem. Soc., 2000, 122, 7195-7201; K. Matsuda and M. Irie, J. Am. Chem. Soc., 2000, 122, 8309-8310.
14. M. N. Leuenberger and D. Loss,Nature, 2001,410, 789-793.
15. K. Tsukagoshi, B. W. Alphenaar and H. Ago, Nature, 1999, 401, 572-574.
16. K. Müllen, M. Baumgarten, N. Tyutyulkov and S. Karabunarliev, Synth. Met., 1991, 40, 127-135.
17. M. Hoshino, K. Kimura and M. Imamura, Chem. Phys. Lett., 1973, 20, 193-196.
18. M. Baumgarten, U. Müller, A. Bohnen and K. Müllen, Angew. Chem., Int. Ed. Engl., 1992, 31, 448-451; U. Müller and M. Baumgarten, J. Am. Chem. Soc., 1995, 117, 5840-5850.
19. M. Baumgarten, U. Müller, A. Bohnen and K. Müllen, Angew. Chem., Int. Ed. Engl., 1992, 31, 448-451; U. Müller and M. Baumgarten, J. Am. Chem. Soc., 1995, 117, 5840-5850.
20. K. Susumu, T. Shimidzu, K. Tanaka and H. Segawa, Tetrahedron Lett., 1996, 37, 8399-8402.
21. R. G. Khoury, L. Jaquinoid and K. M. Smith, Chem. Commun., 1997, 1057-1058.
22. A. Osuka and H. Shimidzu, Angew. Chem., Int. Ed. Engl., 1997, 36, 135-136; N. Yoshida, H. Shimidzu and A. Osuka, Chem. Lett., 1998, 55-56; T. Ogawa, Y. Nishimoto, N. Yoshida, N. Ono and A. Osuka, Angew. Chem., Int. Ed., 1999, 38, 176-179; A. Tsuda, T. Nakamura, S. Sakamoto, K. Yamaguchi and A. Osuka, Angew. Chem., Int. Ed., 2002, 41, 2941-2945.
23. A. Osuka and H. Shimidzu, Angew. Chem., Int. Ed. Engl., 1997, 36, 135-136; N. Yoshida, H. Shimidzu and A. Osuka, Chem. Lett., 1998, 55-56; T. Ogawa, Y. Nishimoto, N. Yoshida, N. Ono and A. Osuka, Angew. Chem., Int. Ed., 1999, 38, 176-179; A. Tsuda, T. Nakamura, S. Sakamoto, K. Yamaguchi and A. Osuka, Angew. Chem., Int. Ed., 2002, 41, 2941-2945.
24. A. Osuka and H. Shimidzu, Angew. Chem., Int. Ed. Engl., 1997, 36, 135-136; N. Yoshida, H. Shimidzu and A. Osuka, Chem. Lett., 1998, 55-56; T. Ogawa, Y. Nishimoto, N. Yoshida, N. Ono and A. Osuka, Angew. Chem., Int. Ed., 1999, 38, 176-179; A. Tsuda, T. Nakamura, S. Sakamoto, K. Yamaguchi and A. Osuka, Angew. Chem., Int. Ed., 2002, 41, 2941-2945.
25. A. Osuka and H. Shimidzu, Angew. Chem., Int. Ed. Engl., 1997, 36, 135-136; N. Yoshida, H. Shimidzu and A. Osuka, Chem. Lett., 1998, 55-56; T. Ogawa, Y. Nishimoto, N. Yoshida, N. Ono and A. Osuka, Angew. Chem., Int. Ed., 1999, 38, 176-179; A. Tsuda, T. Nakamura, S. Sakamoto, K. Yamaguchi and A. Osuka, Angew. Chem., Int. Ed., 2002, 41, 2941-2945.
26. M. Kasha, H. R. Rawls and M. Ashraf El-Bayoumi,Pure Appl. Chem., 1965,11, 371-392.
27. The Porphyrin Handbook Vol. 7, ed. K. M. Kadish, K. M. Smith and R. Guilard, Academic Press, New York, 2000.
28. R. H. Felton and H. Linschitz, J. Am. Chem. Soc., 1966, 88, 1113-1116; J. Fajer, D. C. Borg, A. Forman, D. Dolphin and R. H. Felton, J. Am. Chem. Soc., 1970, 92, 3451-3459; L. D. Spaulding, P. G. Eller, J. A. Bertrand and R. H. Felton, J. Am. Chem. Soc., 1974, 96, 982-987.
29. R. H. Felton and H. Linschitz, J. Am. Chem. Soc., 1966, 88, 1113-1116; J. Fajer, D. C. Borg, A. Forman, D. Dolphin and R. H. Felton, J. Am. Chem. Soc., 1970, 92, 3451-3459; L. D. Spaulding, P. G. Eller, J. A. Bertrand and R. H. Felton, J. Am. Chem. Soc., 1974, 96, 982-987.
30. R. H. Felton and H. Linschitz, J. Am. Chem. Soc., 1966, 88, 1113-1116; J. Fajer, D. C. Borg, A. Forman, D. Dolphin and R. H. Felton, J. Am. Chem. Soc., 1970, 92, 3451-3459; L. D. Spaulding, P. G. Eller, J. A. Bertrand and R. H. Felton, J. Am. Chem. Soc., 1974, 96, 982-987.
31. F. Wu and H. Segawa, Photogr. Sci. Photochem., 1999, 17, 316-322.
32. 4, followed by treatment with zinc powder. After several purifications by the usual silica gel column, the averaged yield was about 98%.
33. A. Tsuda, H. Furuta and A. Osuka, Angew. Chem., Int. Ed., 2000, 39, 2549-2552; A. Tsuda, H. Furuta and A. Osuka, J. Am. Chem. Soc., 2001, 123, 10304-10321.
34. A. Tsuda, H. Furuta and A. Osuka, Angew. Chem., Int. Ed., 2000, 39, 2549-2552; A. Tsuda, H. Furuta and A. Osuka, J. Am. Chem. Soc., 2001, 123, 10304-10321.