Meso,meso′-bis(5-azaindol-2-yl)-appended meso meso-linked Zn(II) diporphyrin: A discrete fluorescent assembly

Organic Letters

Volumn 11, Issue 22, 2009, Pages 5322-5325

  Maeda, Chihiro ^a   Shinokubo, Hiroshi ^b   Osuka, Atsuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5 AZAINDOLE; 5-AZAINDOLE; COPPER; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; METALLOPORPHYRIN; ZINC;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; FLUORESCENCE; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AZA COMPOUNDS; CATALYSIS; COPPER; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; FLUORESCENCE; INDOLES; METALLOPORPHYRINS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; ZINC;

EID: 70749088540     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902294r     Document Type: Article

References (36)

1. (a) McDermott, G.; Prince, S. M.; Freer, A. A.; HawthornthwaiteLawless, A. M.; Papiz, M. Z.; Cogdell, R. J.; Isaacs, N. W. Nature 1995, 374, 517-521.
2. (b) Roszak, A. M.; Howard, T. D.; Southall, J.; Gardiner, A. T.; Law, C. J.; Isaacs, N. W.; Cogdell, T. J. Science 2003, 302, 1969-1972.
3. (a) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 2001, 34, 40-48.
4. (b) Holten, D.; Bocian, D. F.; Lindsey, J. S. Acc. Chem. Res. 2002, 35, 57-69.
5. (c) Choi, M.-S.; Yamazaki, T.; Yamazaki, I.; Aida, T. Angew. Chem., Int. Ed. 2004, 43, 150-158.
6. (d) Kim, D.; Osuka, A. Acc. Chem. Res. 2004, 37, 735-745.
7. Nakamura, Y.; Aratani, N.; Osuka, A. Chem. Soc. Rev. 2007, 36, 831-845.
8. (a) Imamura, T.; Fukushima, K. Coord. Chem. Rev. 2000,198, 133-156.
9. (b) Wojaczyńki, J.; Latos-Grażyński, L. Coord. Chem. Rev. 2000, 204, 113-171.
10. (c) Iengo, E.; Zangrando, E.; Alessio, E. Eur. J. Inorg. Chem. 2003, 2371-2384.
11. (d) Satake, A.; Kobuke, Y. Tetrahedron 2005, 61, 13-41.
12. (e) Maeda, C.; Kamada, T.; Aratani, N.; Osuka, A. Coord. Chem. Rev. 2008, 251, 2743-2752.
13. (a) Sugiura, K.; Tanaka, H.; Matsumoto, T.; Kawai, T.; Sakata, Y. Chem. Lett. 1999, 1193-1194.
14. (b) Sugiura, K.; Fujimoto, Y.; Sakata, Y. Chem. Commun. 2000, 1105-1106.
15. (c) Rucareanu, S.; Mongin, O.; Schuwey, A.; Hoyler, N; Gossauer, A. J. Org. Chem. 2001, 66, 4973-4988.
16. (d) Hoffmann, M.; Wilson, C. J.; Odell, B.; Anderson, H. L. Angew. Chem., Int. Ed. 2007, 46, 3122-3125.
17. (e) Song, J. X.; Jang, S. Y.; Yamaguchi, S; Sankar, J.; Hiroto, S.; Aratani, N; Shin, J.-Y.; Easwaramoorthi, S.; Kim, K. S.; Kim, D.; Shinokubo, H.; Osuka, A. Angew. Chem., Int. Ed. 2008, 47, 6004-6007.
18. (a) Peng, X.; Aratani, N.; Takagi, A.; Matsumoto, T.; Kawai, T.; Hwang, I.-W.; Ahn, T. K.; Kim, D.; Osuka, A. J. Am. Chem. Soc. 2004, 126, 4468-4469.
19. (b) Nakamura, Y.; Hwang, I.-W.; Aratani, N.; Ahn, T. K.; Ko, D. M.; Takagi, A.; Kawai, T.; Matsumoto, T.; Kim, D.; Osuka, A. J. Am. Chem. Soc. 2005, 127, 236-246.
20. (c) Hori, T.; Aratani, N.; Takagi, A.; Matsumoto, T.; Kawai, T.; Yoon, M.-C.; Yoon, Z. S.; Cho, S.; Kim, D.; Osuka, A. Chem.-Eur. J. 2006, 12, 1319-1327.
21. (d) Hori, T.; Peng, X.; Aratani, N.; Takagi, A.; Matsumoto, T.; Kawai, T.; Yoon, Z. S.; Yoon, M.-C.; Yang, J.; Kim, D.; Osuka, A. Chem.-Eur. J. 2008, 14, 582-595.
22. (a) Anderson, H. L.; Sanders, J. K. M. Angew. Chem., Int. Ed. 1990, 29, 1400-1403.
23. (b) Li, J.; Ambroise, A.; Yang, S. I.; Diers, J. R.; Seth, J.; Wack, C. R.; Bocian, D. F.; Holten, D.; Lindsay, J. S. J. Am. Chem. Soc. 1999, 121, 8927-8940.
24. (c) Rucareanu, S.; Schuwey, A.; Gossauer, A. J. Am. Chem. Soc. 2006, 128, 3396-3413.
25. (d) Hoffmann, M.; Kärnbratt, J.; Chang, J. M.-H.; Herz, L. M.; Albinsson, B.; Anderson, H. L. Angew. Chem., Int. Ed. 2008, 47, 4993-4996.
26. (a) Tsuda, A.; Nakamura, T.; Sakamoto, S.; Yamaguchi, K.; Osuka, A. Angew. Chem., Int. Ed. 2002, 41, 2817-2821.
27. (b) Hwang, I.-W.; Kamada, T.; Ahn, T. K.; Ko, D. M.; Nakamura, T.; Tsuda, A.; Osuka, A.; Kim, D. J. Am. Chem. Soc. 2004, 126, 16187-16198.
28. (c) Kamada, T.; Aratani, N; Ikeda, T; Shibata, N.; Higuchi, Y.; Wakamiya, A.; Yamaguchi, S.; Kim, K. S.; Yoon, Z. S.; Kim, D.; Osuka, A. J. Am. Chem. Soc. 2006, 128, 7670-7678.
29. (d) Maeda, C.; Kamada, T.; Aratani, N.; Sasamori, T.; Tokitoh, N.; Osuka, A. Chem-Eur. J. 2009, 15, 9681-9684.
30. Maeda, C.; Shinokubo, H.; Osuka, A. Org. Lett. 2007, 9, 2493-2496.
31. (a) Hiroya, K.; Itoh, S.; Sakamoto, T. J. Org. Chem. 2004, 69, 1126-1136.
32. (b) Sakai, N.; Annaka, K.; Fujita, A.; Sato, A.; Konakahara, T. J. Org. Chem. 2008, 73, 4160-4165.
33. (c) Majumdar, K. C.; Samanta, S.; Chattopadhyay, B. Tetrahedron Lett. 2008, 49, 7213-7216.
34. 2 = 0.2320 (all data), GOF = 1.046.
35. 8c
36. 3 were less than 0.1%.