Strategie synthesis of 2,6-pyridylene-bridged β-to-β porphyrin nanorings through cross-coupling

Chemistry - A European Journal

Volumn 16, Issue 10, 2010, Pages 3009-3012

  Song, Jianxin ^a   Kim, Pyosang ^b   Aratani, Naoki ^a,c   Kim, Dongho ^b   Shinokubo, Hiroshi ^d   Osuka, Atsuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b Yonsei University   (South Korea)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^d NAGOYA UNIVERSITY   (Japan)

Author keywords

Cross coupling; Fluorescence; Host guest chemistry; Nanorings; Porphyrinoids

Indexed keywords

CROSS-COUPLING; CROSS-COUPLINGS; EXCITED ENERGIES; FLUORESCENT LIFETIME; GOOD YIELD; HOSTGUEST CHEMISTRY; PALLADIUM-CATALYZED CROSS-COUPLINGS; PHOTOPHYSICAL STUDIES; PORPHYRINOIDS;

CHROMOPHORES; ENERGY TRANSFER; FLUORESCENCE; NANORINGS; PALLADIUM; PORPHYRINS; SYNTHESIS (CHEMICAL);

NANOSTRUCTURED MATERIALS;

EID: 77649198511     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903177     Document Type: Article

References (33)

1. G. McDermott, S. M. Prince, A. A. Freer, A. M. HawthornlhwaileLawless, M. Z. Papiz, R. J. Cogdell, N. W. Isaacs, Nature 1995, 374, 517.
2. J. Koepke. X. Hu, C. Muenke, K. Schulten. H. Michel, Structure 1996, 4, 581.
3. A. W. Roszak, T. D. Howard, J. Soulhall. A. T. Gardiner. C. J. Law, N. W. Isaacs, R. J. Cogdell, Science 2003, 302, 1969.
4. Y. Nakamura, N. Aralani. A. Osuka, Chem. Soc. Rev. 2007, 36, 831.
5. S. Anderson, H. L. Anderson, J. K. M. Sanders, Acc. Chem. Res. 1993, 26, 469.
6. J. Yang, D. Kim, J. Mater, Chem. 2009, 19, 1057.
7. J. E. Raymond, A. Bhaskar, T. Goodson III, N. Makiuchi, K. Ogawa, Y. Kobuke, J. Am. Chem. Soc. 2008, 130, 17212.
8. X. Chi, A. J. Guerin, R. A. Haycock, C. A. Hunter, L. D. Sarson, J. Chem. Soc. Chem. Commun. 1995, 2567.
9. a) J. Li, A. Ambroise, S. I. Yang, J. R. Diers, J. Seth, C. R. Wack, D. F. Bocian, D. Holten, J. S. Lindsey, J. Am. Chem. Soc. 1999, 121, 8927;
10. b) O. Mongin, A. Schuwey, M.-A. Vallot, A. Gossauer, Tetrahedron Lett. 1999, 40, 8347.
11. a) Y. Kuramochi, A. Satake, Y. Kobuke, J. Am. Chem. Soc. 2004, 126, 8668;
12. b) F. Hajjaj, Z. S. Yoon, M.-C. Yoon, J. Park, A. Satake, D. Kim, Y. Kobuke, J. Am. Chem. Soc. 2006, 128, 4612.
13. a) K.-i. Sugiura, Y. Fujimoto, Y. Sakata, Chem. Commun. 2000, 1105;
14. b) A. Kato, K.-i. Sugiura, H. Miyasaka, H. Tanaka, T. Kawai, M. Sugimoto, M. Yamashita, Chem. Lett. 2004, 33, 578.
15. a) X. Peng, N. Aratani, A. Takagi, T. Matsumoto, T. Kawai, I.-W. Hwang, T. K. Ahn, D. Kim, A. Osuka, J. Am. Chem. Soc. 2004, 126, 4468;
16. b) T. Hori, N. Aratani, A. Takagi, T. Matsumoto, T. Kawai, M.-C. Yoon, Z. S. Yoon, S. Cho, D. Kim, A. Osuka, Chem. Eur. J. 2006, 12, 1319;
17. c) Y. Nakamura, N. Aratani, H. Shinokubo, A. Takagi, T. Kawai, T. Matsumoto, Z. S. Yoon, D. Y. Kim, T. K. Ahn, D. Kim, A. Muranaka, N. Kobayashi, A. Osuka, J. Am. Chem. Soc. 2006, 128, 4119.
18. a) I. Hisaki, S. Hiroto, K. S. Kim, S. B. Noh, D. Kim, H. Shinokubo, A. Osuka, Angew. Chem. 2007, 119, 5217;
19. Angew. Chem. Int. Ed. 2007, 46, 5125;
20. b) J. Song, S. Y. Jang, S. Yamaguchi, J. Sankar, S. Hiroto, N. Aratani, J.-Y. Shin, S. Easwaramoorthi, K. S. Kim, D. Kim, H. Shinokubo, A. Osuka, Angew. Chem. 2008, 120, 6093;
21. Angew. Chem. Int. Ed. 2008, 47, 6004.
22. H. Hata, H. Shinokubo, A. Osuka, J. Am. Chem. Soc. 2005, 127, 8264.
23. 11H NMR spectroscopy measurements of the trimers to prevent overlapping of solvent signal with the aryl peaks.
24. [21] CCDC-754843 and 754844 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
25. Y. H. Kim, D. H. Jeong, D. Kim, S. C. Jeoung, H. S. Cho, S. K. Kim, N. Aratani, A. Osuka, J. Am. Chem. Soc. 2001, 123, 76.
26. Y. Inokuma, Z. S. Yoon, D. Kim, A. Osuka, J. Am. Chem. Soc. 2007, 129, 4747.
27. a) A. Ambroise, J. Li, L. Yu, J. S. Lindsey, Org. Lett. 2000, 2, 2563;
28. b) L. Yu, J. S. Lindsey, J. Org. Chem. 2001, 66, 7402;
29. c) A. Ambroise, C. Kirmaier, R. W. Wagner, R. S. Loewe, D. F. Bocian, D. Holten, J. S. Lindsey, J. Org. Chem. 2002, 67, 3811.
30. a) H. S. Cho, D. H. Jeong, S. Cho, D. Kim, Y. Matsuzaki, K. Tanaka, A. Tsuda, A. Osuka, J. Am. Chem. Soc. 2002, 124, 14642;
31. b) Y. H. Kim, D. H. Jeong, D. Kim, S. C. Jeoung, H. S. Cho, S. K. Kim, N. Aratani, A. Osuka, J. Am. Chem. Soc. 2001, 123, 76.
32. Squeeze-Platon: a) PLATON, A Multipurpose Crystallographic Tool, A. L. Spek, Utrecht University, Utrecht, 2008;
33. b) P. van der Sluis, A. L. Spek, Acta Crystallogr. Sect. A 1990, 46, 194.