Free-radical polymerization of dibenzofulvene leading to a π-stacked polymer: Structure and properties of the polymer and proposed reaction mechanism

Macromolecules

Volumn 38, Issue 20, 2005, Pages 8140-8148

  Nakano, Tamaki ^a   Yade, Tohru ^a   Fukuda, Yasuyuki ^a   Yamaguchi, Takashi ^a   Okumura, Shohei ^a  

^a NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANIONIC POLYMERIZATION; CHEMICAL BONDS; CONFORMATIONS; FLUORESCENCE; ISOMERIZATION; MOLECULAR STRUCTURE; MONOMERS; ORGANIC COMPOUNDS; REACTION KINETICS; SOLUBILITY; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

AROMATIC SUBSTITUTION; CONFORMATION SPECIFICITY; DIBENZOFULVENE (DBF); POLYMERIZATION PRODUCTS;

FREE RADICAL POLYMERIZATION;

EID: 26944440086     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma0513564     Document Type: Article

References (53)

1. Nakano, T.; Takewaki, K.; Yade, T.; Okamoto, Y. J. Am. Chem. Soc. 2001, 123, 9182-9183.
2. Nakano, T.; Yade, T. J. Am. Chem. Soc. 2003, 125, 15474-15484.
3. Nakano, T.; Nakagawa, O.; Tsuji, M.; Tanikawa, M.; Yade, T.; Okamoto, Y. Chem. Commun. 2004, 144-145.
4. Nakano, T.; Nakagawa, O.; Yade, T.; Okamoto, Y. Macromolecules 2003, 36, 1433-1435.
5. For reviews of helical polymers and oligomers, see: (a) Okamoto, Y.; Nakano, T. Chem. Rev. 1994, 94, 349-372.
6. (b) Green, M. M.; Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. Angew. Chem., Int. Ed. 1999, 38, 3138-3154.
7. (c) Fujiki, M. Macromol. Rapid Commun. 2001, 22, 539-563.
8. Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4012.
9. (e) Nakano, T.; Okamoto, Y. Chem. Rev. 2001, 101, 4013-4038.
10. (f) Conrnelissen, J. J. L. M.; Rowan, A. E.; Nolte, R. J. M.; Sommerdijk, N. A. J. M. Chem. Rev. 2001, 101, 4039-4070.
11. Nakano, T.; Yade, T.; Yokoyama, M.; Nagayama, N. Chem. Lett. 2004, 33, 296-297.
12. Forero, S.; Nguyen, P. H.; Brütting, W.; Schwoerer, M. Phys. Chem. Chem. Phys. 1999, 1, 1769-1776.
13. Kepler, R. G.; Zeigler, J. M.; Kurtz, S. R. Phys. Rev. B 1987, 35, 2818-2822.
14. Pearson, J. M.; Stolka, M. Poly(N-vinylcarbazole); Gordon and Breach: New York, 1981; Chapter 4.
15. (a) Redecker, M.; Bradley, D. D. C.; Inbasekaran, M.; Woo, E. Appl. Phys. Lett. 1999, 74, 1400-1402.
16. (b) Redecker, M.; Bradley, D. D. C.; Inbasekaran, M.; Woo, E. Appl. Phys. Lett. 1998, 73, 1565-1567.
17. Babel, A.; Jenekhe, S. A. J. Phys. Chem. B 2003, 107, 1749-1754.
18. (a) Okamoto, Y.; Habaue, S.; Isobe, Y.; Suito, Y. Macromol. Symp. 2003, 195, 75-80.
19. (b) Tsuji, M.; Sakai, R.; Satoh, T.; Kaga, H.; Kakuchi, T.; Macromolecules 2002, 35, 8255-8257.
20. (c) Miura, Y.; Satoh, T.; Narumi, A.; Nishizawa, O.; Okamoto, Y.; Kakuchi, T. Macromolecules 2005, 38, 1041-1043.
21. (d) Ray, B.; Isobe, Y.; Morioka, K.; Habaue, S.; Okamoto, Y.; Kamigaito, M.; Sawamoto, M. Macromolecules 2003, 36, 543-545.
22. (e) Matsumoto, A.; Tanaka, T.; Tsubouchi, T.; Tashiro, K.; Saragai, S.; Nakamoto, S. J. Am. Chem. Soc. 2002, 124, 8891-8902.
23. (a) Nakano, T.; Mori, M.; Okamoto, Y. Macromolecules 1993, 26, 867-868.
24. (b) Nakano, T.; Shikisai, Y.; Okamoto, Y. Polym. J. 1996, 28, 51-60.
25. (c) Nakano, T.; Mori, M.; Okamoto, Y. Macromolecules 1999, 32, 2391-2393.
26. (d) Nakano, T.; Tsunematsu, K.; Okamoto, Y. Chem. Lett. 2002, 42-43.
27. Nakano, T.; Matsuda, A.; Okamoto, Y. Polym. J. 1996, 28, 556-558.
28. Hoshikawa, N.; Hotta, Y.; Okamoto, Y. J. Am. Chem. Soc. 2003, 125, 12380-12381.
29. Greenhow, E. J.; McNeil, D.; White, E. N. J. Chem. Soc. 1952, 986-992.
30. More O'Ferrall, R. A.; Slae, S. J. Chem. Soc., Chem. Commun. 1969, 486-487.
31. Eaton, D. F. Pure Appl. Chem. 1988, 60, 1107-1114.
32. Stewart, J. J. P. MOPAC2002 software; Fujitsu Limited: Tokyo, Japan, 2001.
33. Sun, H. J. Phys. Chem. 1998, 102, 7338-7364.
34. Berendsen, H. J. C.; Postma, J. P. M.; van Gunsteren, W. F.; DiNola, A.; Haak, J. R. J. Chem. Phys. 1984, 81, 3684-3690.
35. (a) Evans, A.; George, D. J. Chem. Soc. 1961, 4653-4659.
36. (b) Evans, A. G.; George, D. B. J. Chem. Soc. 1962, 141-146.
37. (c) Yuki, H.; Hotta, J.; Okamoto, Y.; Murahashi, S. Bull. Chem. Soc. Jpn. 1967, 40, 2659-2663.
38. Richards, D. H.; Scilly, N. F. J. Polym. Sci., Polym. Lett. 1969, 7, 99-101.
39. (a) Okamoto, Y.; Mohri, H.; Nakano, T.; Hatada, K. J. Am. Chem. Soc. 1989, 111, 5952-5954.
40. (b) Okamoto, Y.; Mohri, H.; Nakano, T.; Hatada, K. Chirality 1991, 3, 277-284.
41. (a) Graham, W. D.; Green, J. D.; Pyror, W. A. J. Org. Chem. 1979, 44, 907-914.
42. (b) Husain, A.; Hamielec, A. H. J. Appl. Polym. Sci. 1978, 22, 1207-1223.
43. (c) Olaj, O. F.; Kauffmann, H. F.; Breitenbach, J. W. Makromol. Chem. 1976, 177, 3065-3071.
44. Moad, G.; Solomon, D. H. In The Chemistry of Free Radical Polymerization; Pergamon: Oxford, 1995; pp 175-183.
45. Nakano, T.; Matsuda, A.; Okamoto, Y. Polym. J. 1996, 28, 556-558.
46. Watson, J. D.; Crick, F. H. C. Nature (London) 1953, 171, 737-738.
47. Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793-1796.
48. (a) Lokey, R. S.; Iverson, B. L. Nature (London) 1995, 375, 303-305.
49. (b) Nguyen, J. Q.; Iverson, B. L. J. Am. Chem. Soc. 1999, 121, 2639-2640.
50. (a) Wang, W.; Li, L.-S.; Helms, G.; Zhou, H.-H.; Li, A. D. Q. J. Am. Chem. Soc. 2003, 125, 1120-1121.
51. (b) Li, A. D.'Q.; Wang, W.; Wang, L.-Q. Chem.-Eur. J. 2003, 9, 4594-4601.
52. (c) Wang, W.; Han, J. J.; Wang, L.-Q.; Li, L.-S.; Shaw, W. J.; Li, A. D. Q. Nano Lett. 2003, 3, 455-458.
53. Morisaki, Y.; Chujo, Y. Tetrahedron Lett. 2005, 46, 2533-2537.