Discrete cyclic porphyrin arrays as artificial light-harvesting antenna

Accounts of Chemical Research

Volumn 42, Issue 12, 2009, Pages 1922-1934

  Aratani, Naoki ^a   Kim, Dongho ^b   Osuka, Atsuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN;

ARTICLE; CHEMISTRY; CONFORMATION; ENERGY TRANSFER; PHOTOSYNTHESIS; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; ENERGY TRANSFER; MOLECULAR CONFORMATION; PHOTOSYNTHESIS; PORPHYRINS; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 72949094187     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar9001697     Document Type: Article

References (33)

1. McDermott, G.; Prince, S. M.; Freer, A. A.; Hawthornthwaite-Lowless, A. M.; Papiz, M. Z.; Cogdell, R. J.; Isaacs, N. W. Crystal Structure of an Integral Membrane Light- Harvesting Complex from Photosynthetic Bacteria. Nature 1995, 374, 517-521.
2. (a) Osuka, A.; Maruyama, K. Synthesis of Naphthalene-bridged Porphyrin Dimers and their Orientation-Dependent Exciton Coupling. J. Am. Chem. Soc. 1988, 110, 4454-4456.
3. (b) Osuka, A.; Maruyama, K.; Mataga, N.; Asahi, T.; Yamazaki, I.; Tamai, N. Geometry Dependence of Intramolecular Photoinduced Electron Transfer in Synthetic Zinc-ferric Hybrid Diporphyrins. J. Am. Chem. Soc. 1990, 112, 4958-4959.
4. Osuka, A.; Shimidzu, H. meso, meso-Linked Porphyrin Arrays. Angew. Chem., Int. Ed. Engl. 1997, 36, 135-137.
5. Aratani, N.; Osuka, A.; Kim, Y. H.; Jeong, D. H.; Kim, D. Extremely Long, Discrete mesomeso- Coupled Porphyrin Arrays. Angew. Chem., Int. Ed. 2000, 39, 1458-1462.
6. Nakano, A.; Osuka, A.; Yamazaki, I.; Yamazaki, T.; Nishimura, Y. Windmill-like Porphyrin Arrays as Potent Light-Harvesting Antenna Complexes. Angew. Chem., Int. Ed. 1998, 37, 3023-3027.
7. Nakano, A.; Yamazaki, T.; Nishimura, Y.; Yamazaki, I.; Osuka, A. Three- Dimensionally Arranged Windmill and Grid Porphyrin Arrays by AgI-Promoted mesomeso Block Oligomerization. Chem.sEur. J. 2000, 6, 3254-3271.
8. Hori, T.; Nakamura, Y.; Aratani, N.; Osuka, A. Exploration of Electronically Interactive Cyclic Porphyrin Arrays. J. Organomet. Chem. 2007, 692, 148-155.
9. Maeda, C.; Kamada, T.; Aratani, N.; Osuka, A. Chiral Self-Discriminative Self- Assembling of meso-meso-Linked Diporphyrins. Coord. Chem. Rev. 2007, 251, 2743-2752.
10. Nakamura, Y.; Aratani, N.; Osuka, A. Cyclic Porphyrin Arrays as Artificial Photosynthetic Antenna: Synthesis and Excitation Energy Transfer. Chem. Soc. Rev. 2007, 36, 831-845.
11. Anderson, S.; Anderson, H. L.; Sanders, J. K. M. Expanding Roles for Templates in Synthesis. Acc. Chem. Res. 1993, 26, 469-475.
12. Aratani, N.; Takagi, A.; Yanagawa, Y.; Matsumoto, T.; Kawai, T.; Yoon, Z. S.; Kim, D.; Osuka, A. Giant meso-meso-Linked Porphyrin Arrays of Micrometer Molecular Length and Their Fabrication. Chem.sEur. J. 2005, 11, 3389-3404.
13. Aratani, N.; Osuka, A. Synthesis of meso-meso Linked Hybrid Porphyrin Arrays by Pd-Catalyzed Cross-Coupling Reaction. Org. Lett. 2001, 3, 4213-4216.
14. Shinokubo, H.; Osuka, A. Marriage of Porphyrin Chemistry with Metal-Catalysed Reactions. Chem. Commun. 2009, 1011-1021.
15. Aratani, N.; Osuka, A. A meso-meso Directly Linked Octameric Porphyrin Square. Chem. Commun. 2008, 4067-4069.
16. Nakamura, Y.; Jang, S. Y.; Tanaka, T.; Aratani, N.; Lim, J. M.; Kim, K. S.; Kim, D.; Osuka, A. Two-Dimensionally Extended Porphyrin Tapes: Synthesis and Shape- Dependent Two-Photon Absorption Properties. Chem.-Eur. J. 2008, 14, 8279-8289.
17. Tsuda, A.; Osuka, A. Fully Conjugated Porphyrin Tapes with Electronic Absorption Bands That Reach into Infrared. Science 2001, 293, 79-82.
18. Kasha, M.; Rawls, H. R.; El-Bayoumi, M. A. The Exciton Model in Molecular Spectroscopy. Pure Appl. Chem. 1965, 11, 371-392.
19. Nakamura, Y.; Hwang, I.-W.; Aratani, N.; Ahn, T. K.; Ko, D. M.; Takagi, A.; Kawai, T.; Matsumoto, T.; Kim, D.; Osuka, A. Directly meso-meso-Linked Porphyrin Rings: Synthesis, Characterization, and Efficient Excitation Energy Hopping. J. Am. Chem. Soc. 2005, 127, 236-246.
20. Peng, X.; Aratani, N.; Takagi, A.; Matsumoto, T.; Kawai, T.; Hwang, I.-W.; Ahn, T. K.; Kim, D.; Osuka, A. A Dodecameric Porphyrin Wheel. J. Am. Chem. Soc. 2004, 126, 4468-4469.
21. Hwang, I.-W.; Ko, D. M.; Ahn, T. K.; Yoon, Z. S.; Kim, D.; Peng, X.; Aratani, N.; Osuka, A. Excitation Energy Migration in a Dodecameric Porphyrin Wheel. J. Phys. Chem. B 2005, 109, 8643-8651. (Pubitemid 40750894)
22. Hori, T.; Aratani, N.; Takagi, A.; Matsumoto, T.; Kawai, T.; Yoon, M.-C.; Yoon, Z. S.; Cho, S.; Kim, D.; Osuka, A. Giant Porphyrin Wheels with Large Electronic Coupling as Models of Light-Harvesting Photosynthetic Antenna. Chem.sEur. J. 2006, 12, 1319-1327.
23. Roszak, A. W.; Howard, T. D.; Southall, J.; Gardiner, A. T.; Law, C. J.; Isaacs, N. W.; Cogdell, R. J. Crystal Structure of the RC-LH1 Core Complex from Rhodopseudomonas palustris. Science 2003, 302, 1969-1972.
24. Hori, T.; Peng, X.; Aratani, N.; Takagi, A.; Matsumoto, T.; Kawai, T.; Yoon, Z. S.; Yoon, M.-C.; Yang, J.; Kim, D.; Osuka, A. Synthesis of Nanometer-Scale Porphyrin Wheels of Variable Size. Chem.sEur. J. 2008, 14, 582-595.
25. Chi, X.; Guerin, A. J.; Haycock, R. A.; Hunter, C. A.; Sarson, L. D. The Thermodynamics of Self-Assembly. J. Chem. Soc., Chem. Commun. 1995, 2563-2565.
26. (a) Takahashi, R.; Kobuke, Y. Hexameric Macroring of Gable-Porphyrins as a Light- Harvesting Antenna Mimic. J. Am. Chem. Soc. 2003, 125, 2372-2373.
27. Wu, A.; Isaacs, L. Self-Sorting: The Exception or the Rule. J. Am. Chem. Soc. 2003, 125, 4831-4835.
28. Tsuda, A.; Nakamura, T.; Sakamoto, S.; Yamaguchi, K.; Osuka, A. A Self-Assembled Porphyrin Box from meso-meso-Linked Bis{5-p-pyridyl-15-(3,5-di- octyloxyphenyl) porphyrinato zinc(II)}. Angew. Chem., Int. Ed. 2002, 41, 2817-2821.
29. Hwang, I.-W.; Kamada, T.; Ahn, T. K.; Ko, D. M.; Nakamura, T.; Tsuda, A.; Osuka, A.; Kim, D. Porphyrin Boxes Constructed by Homochiral Self-Sorting Assembly: Optical Separation, Exciton Coupling, and Efficient Excitation Energy Migration. J. Am. Chem. Soc. 2004, 126, 16187-16198.
30. Kamada, T.; Aratani, N.; Ikeda, T.; Shibata, N.; Higuchi, Y.; Wakamiya, A.; Yamaguchi, S.; Kim, K. S.; Yoon, Z. S.; Kim, D.; Osuka, A. High Fidelity Self-Sorting Assembling of meso-Cinchomeronimide Appended meso-meso-Linked Zn(II) Diporphyrins. J. Am. Chem. Soc. 2006, 128, 7670-7678.
31. Rigler, R.; Orrit, M.; Basché , T. Single Molecule Spectroscopy; Springer: Heidelberg, Germany, 2002.
32. Park, M.; Yoon, M.-C.; Yoon, Z. S.; Hori, T.; Peng, X.; Aratani, N.; Hotta, J.-i.; Uji-i, H.; Sliwa, M.; Hofkens, J.; Osuka, A.; Kim, D. Single-Molecule Spectroscopic Investigation of Energy Migration Processes in Cyclic Porphyrin Arrays. J. Am. Chem. Soc. 2007, 129, 3539-3544.
33. Yang, J.; Park, M.; Yoon, Z. S.; Hori, T.; Peng, X.; Aratani, N.; Dedecker, P.; Hotta, J.-i.; Uji-i, H.; Sliwa, M.; Hofkens, J.; Osuka, A.; Kim, D. Excitation Energy Migration Processes in Cyclic Porphyrin Arrays Probed by Single Molecule Spectroscopy. J. Am. Chem. Soc. 2008, 130, 1879-1884.