A new synthesis of functional dyes from 2-acenaphtho[1,2-c]pyrrole

Heterocycles

Volumn 61, Issue , 2003, Pages 433-447

  Ono, Noboru ^a   Yamamoto, Takanori ^a   Shimada, Naomi ^a   Kuroki, Kenji ^a   Wada, Mitsuo ^a   Utsunomiya, Ryouhei ^a   Yano, Tomoko ^a   Uno, Hidemitsu ^a   Murashima, Takashi ^b  

^a EHIME UNIVERSITY   (Japan)

^b KONAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 ACENAPHTHO[1,2 C]PYRROLE; DYE; POLYMER; PORPHYRIN DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

EID: 0347651908     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-03-S58     Document Type: Article

References (35)

1. D. H. R. Barton, J. Kervagoret, and S. Zard, Tetrahedron, 1990, 46, 7587.
2. N. Ono, H. Kawamura, M. Bougauchi, and K. Maruyama, Tetrahedron, 1990, 46, 7483; Y. Fumoto, T. Eguchi, H. Uno, and N. Ono, J. Org. Chem., 1999, 64, 6518; M. Adamzyk, D. D. Johnson, and R. E. Reddy, Angew. Chem., Int. Ed., 1999, 38, 3537; N. Ono, The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001, pp. 330-338.
3. N. Ono, H. Kawamura, M. Bougauchi, and K. Maruyama, Tetrahedron, 1990, 46, 7483; Y. Fumoto, T. Eguchi, H. Uno, and N. Ono, J. Org. Chem., 1999, 64, 6518; M. Adamzyk, D. D. Johnson, and R. E. Reddy, Angew. Chem., Int. Ed., 1999, 38, 3537; N. Ono, The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001, pp. 330-338.
4. N. Ono, H. Kawamura, M. Bougauchi, and K. Maruyama, Tetrahedron, 1990, 46, 7483; Y. Fumoto, T. Eguchi, H. Uno, and N. Ono, J. Org. Chem., 1999, 64, 6518; M. Adamzyk, D. D. Johnson, and R. E. Reddy, Angew. Chem., Int. Ed., 1999, 38, 3537; N. Ono, The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001, pp. 330-338.
5. N. Ono, H. Kawamura, M. Bougauchi, and K. Maruyama, Tetrahedron, 1990, 46, 7483; Y. Fumoto, T. Eguchi, H. Uno, and N. Ono, J. Org. Chem., 1999, 64, 6518; M. Adamzyk, D. D. Johnson, and R. E. Reddy, Angew. Chem., Int. Ed., 1999, 38, 3537; N. Ono, The Nitro Group in Organic Synthesis, Wiley-VCH, New York, 2001, pp. 330-338.
6. (a) N. Ono, H. Hironaga, K. Simizu, K. Ono, K. Kuwano, and T. Ogawa, J. Chem. Soc., Chem. Commun., 1994, 1019;
7. (b) N. Ono, H. Hironaga, K. Ono, S. Kaneko, T. Murashima, T. Ueda, C. Tsukamura, and T. Ogawa, J. Chem. Soc., Perkin Trans. 1, 1996, 417;
8. (c) T. Murashima, R. Tamai, K. Fujita, H. Uno, and N. Ono, Tetrahedron Lett., 1996, 37, 8391;
9. (d) T. Murashima, R. Tamai, K. Nishi, K. Nomura, K. Fujita, H. Uno, and N. Ono, J. Chem. Soc., Perkin Trans 1, 2000, 995.
10. (a) T. D. Lash and P. Chandraseker, J. Am. Chem. Soc., 1996, 118, 8767;
11. (b) J. D. Spence and T. D. Lash, J. Org. Chem., 2000, 65, 1530;
12. (c) T. D. Lash, T. M. Werner, M. L. Thompson, and J. M. Manley, J. Org. Chem., 2001, 66, 3152 and references therein.
13. L. Jaquinod, C. Gros, M. M. Olmstead, and K. M. Smith, Chem. Commun., 1996, 1475.
14. T. D. Lash, The Porphyrin Handbook, ed. by K. M. Kadish, K. M. Smith and R. Guilard, Academic Press, San Diego, 2, 2000, pp. 157-230 and references therein.
15. B. Valeur, Molecular Fluorescence, Wiley-VCH, Weinheim, 2002.
16. W. Rettig and J. Wirz, Helv. Chim. Acta, 1976, 59, 1054.
17. L. deWitt, G. J. Blanchar, E. LeGoff, M. E. benz, J. H. Liao, and M. G. Kanatzidis, J. Am. Chem. Soc., 1993, 115, 12158.
18. R. E. Martin and F. Diederich, Angew. Chem., Int. Ed., 1999, 38, 1350.
19. (a) A. Pelter and D. E. Jones, J. Chem. Soc., Perkin Trans. 1, 2000, 2289;
20. (b) T. M. Swager, C. J. Gil, and M. S. Wrighton, J. Phys. Chem., 1995, 99, 4886 and references therein.
21. N. Ono, C. Tsukamura, Y. Nomura, H. Hironaga, T. Murashima, and T. Ogawa, Adv. Mater., 1997, 9, 149.
22. K. Mullen and G. Wegner, Electronic Materials: The Oligomer Approach, Wiley-VCH, Weinheim, 1998;
23. B. Valeur, Molecular Fluorescence, Wiley-VCH, Weimheim, 2001 and references therein
24. T. E. O. Screen, J. R. G. Thorme, R. G. Denning, D. G. Bucknall, and H. L. Anderson, J. Am. Chem. Soc., 2002, 124, 9712; A. Tsuda and A. Osuka, Science, 2001, 293, 79; H. L. Anderson, Chem. Commun., 1999, 2323 and many references therein.
25. T. E. O. Screen, J. R. G. Thorme, R. G. Denning, D. G. Bucknall, and H. L. Anderson, J. Am. Chem. Soc., 2002, 124, 9712; A. Tsuda and A. Osuka, Science, 2001, 293, 79; H. L. Anderson, Chem. Commun., 1999, 2323 and many references therein.
26. T. E. O. Screen, J. R. G. Thorme, R. G. Denning, D. G. Bucknall, and H. L. Anderson, J. Am. Chem. Soc., 2002, 124, 9712; A. Tsuda and A. Osuka, Science, 2001, 293, 79; H. L. Anderson, Chem. Commun., 1999, 2323 and many references therein.
27. N. Ono, H. Miyagawa, T. Ueta, T. Ogawa, and H. Tani, J. Chem. Soc., Perkin Trans. 1, 1998, 1595.
28. T. Murashima, N. Wakamori, Y. Uchihara, T. Ogawa, H. Uno, and N. Ono, Mol. Cryst. Liq. Cryst., 1996, 278, 165;
29. A. Merz, R. Schropp, and E. Dotterl, Synthesis, 1995, 795.
30. K. Zong and J. R. Reynolds, J. Org. Chem., 2001, 66, 6873 and references therein.
31. A. Burghart, H. Kim, M. B. Welch, L. H. Thoresen, J. Reibenzpies, K. Burgstorm, and L. B. A. Johansson, J. Org. Chem., 1999, 64, 7813; J. Chen, A. burghart, A. D. kovac, and K. Burgess, J. Org. Chem., 2000, 65, 2900; K. rurack, M. kollmannsberger, and J. Daub, Angew. Chem., Int. Ed., 2001, 40, 385 and references therein.
32. A. Burghart, H. Kim, M. B. Welch, L. H. Thoresen, J. Reibenzpies, K. Burgstorm, and L. B. A. Johansson, J. Org. Chem., 1999, 64, 7813; J. Chen, A. burghart, A. D. kovac, and K. Burgess, J. Org. Chem., 2000, 65, 2900; K. rurack, M. kollmannsberger, and J. Daub, Angew. Chem., Int. Ed., 2001, 40, 385 and references therein.
33. A. Burghart, H. Kim, M. B. Welch, L. H. Thoresen, J. Reibenzpies, K. Burgstorm, and L. B. A. Johansson, J. Org. Chem., 1999, 64, 7813; J. Chen, A. burghart, A. D. kovac, and K. Burgess, J. Org. Chem., 2000, 65, 2900; K. rurack, M. kollmannsberger, and J. Daub, Angew. Chem., Int. Ed., 2001, 40, 385 and references therein.
34. M. Wada, S. Ito, H. Uno, T. Murashima, N. Ono, T. Urano, and Y. Urano, Tetrahedron Lett., 2001, 42, 6711.
35. M. Shah, K. Thangaraji, M. L. Soong, L. T. Wolford, J. H. Boyer, I. R. Politer, and T. G. Pavlopoulos, Heteroatom Chemistry, 1990, 1, 389.