Windmill-like porphyrin arrays as potent light-harvesting antenna complexes

Angewandte Chemie - International Edition

Volumn 37, Issue 21, 1998, Pages 3023-3027

  Nakano, Aiko ^a   Osuka, Atsuhiro ^a   Yamazaki, Iwao ^b   Yamazaki, Tomoko ^b   Nishimura, Yoshinobu ^b  

^a KYOTO UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

C C coupling; Donor acceptor systems photosynthesis; Porphyrinoids; Supramolecular chemistry

Indexed keywords

NICKEL; PORPHYRIN; ZINC;

ARTICLE; CHEMISTRY; COMPLEX FORMATION; ENERGY TRANSFER; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; GEL PERMEATION CHROMATOGRAPHY; IRRADIATION; PHOTOSYNTHESIS;

EID: 0032538774     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981116)37:21<3023::AID-ANIE3023>3.0.CO;2-A     Document Type: Article

References (26)

1. T. Pullerits, V. Sundström, Acc. Chem. Res. 1996, 29, 381.
2. M. R. Wasielewski, Chem. Rev. 1992, 92, 435.
3. A. Osuka, K. Maruyama, J. Am. Chem. Soc. 1988, 110, 4454;
4. T. Nagata, A. Osuka, K. Maruyama, J. Am. Chem. Soc. 1990, 112, 3054.
5. J.-M. Lehn, Supramolecular Chemistry-Concepts and Perspectives, VCH, Weinheim, 1995;
6. C. M. Drain, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1994, 2313;
7. S. Prathapan, T. E. Johnson, J. S. Lindsey, J. Am. Chem. Soc. 1993, 115, 7519;
8. R. W. Wagner, J. S. Lindsey, J. Am. Chem. Soc. 1994, 116, 9759;
9. R. W. Wagner, J. S. Lindsey, J. Serth, V. Palaniappan, D. F. Bocian, J. Am. Chem. Soc. 1996, 118, 3996;
10. K. Funatsu, A. Kimura, T. Imamura, Y. Sasaki, Chem. Lett. 1995, 765.
11. H. Higuchi, M. Takeuchi, J. Ojima, Chem. Lett. 1996, 593;
12. O. Mongin, A. Gossauer, Tetrahedron 1997, 20, 6835.
13. L. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney, A. M. Marguerettaz, J. Org. Chem. 1987, 52, 827;
14. J. L. Sessler, V. L. Capuano, Angew. Chem. 1990, 102, 1162;
15. Angew. Chem. Int. Ed. Engl. 1990, 29, 1134.
16. A. Osuka, H. Shimidzu, Angew. Chem. 1997, 109, 93;
17. Angew. Chem. Int. Ed. Engl. 1997, 36, 135;
18. N. Yoshida, H. Shimidzu, A. Osuka, Chem. Lett. 1998, 55;
19. meso-meso-linked porphyrin dimers were prepared independently by other nondirect routes: K. Susumu, T. Shimizu, K. Tanaka, H. Segawa, Tetrahedron Lett. 1996, 37, 8399;
20. R. G. Khoury, L. Jaquinod, K. M. Smith, Chem. Commun. 1997, 1057.
21. T. Ogawa, Y. Nishimoto, N. Yosida, N. Ono, A. Osuka, Chem. Commun. 1998, 337.
22. 3 to be 0.17, 0.32, 0.40, and 0.31 V, respectively, versus ferrocene/ferrocenium ion.
23. 1H NMR spectroscopy (500 MHz) as well as FAB and MALDITOF mass spectrometry.
24. 1H NMR spectra of the 15-mer and 20-mer precluded their full characterization. These results may imply that not only the linear porphyrin arrays but also the windmill-like orthogonal porphyrin arrays are useful building blocks.
25. Since the energy difference between the singlet excited state of the meso-meso diporphyrin and the peripheral porphyrin rings is small (0.07 eV), the energy transfer may be reversible and the dynamics of the photoexcited state of the windmill-like porphyrin arrays are very complicated.
26. A. Aviram, J. Am. Chem. Soc. 1988, 110, 5687.