Hain multiplying controlled cationic polymerization of isobutyl vinyl ether using pyrrole: Increment of propagating chains by efficient "initiator-like" transfer agent

Macromolecules

Volumn 43, Issue 8, 2010, Pages 3682-3689

  Kanazawa, Arihiro ^a   Kanaoka, Shokyoku ^a   Aoshima, Sadahito ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOCATIONS; END STRUCTURE; ISOBUTYL; LEWIS BASE; METAL CHLORIDES; NARROW MOLECULAR WEIGHT DISTRIBUTIONS; NUMBER-AVERAGE; SILYL KETENE ACETAL; TRANSFER AGENTS; TRANSFER REACTION; VINYL ETHERS;

ACIDS; CHLORINE COMPOUNDS; ETHERS; MOLECULAR WEIGHT DISTRIBUTION; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS; POLYMERS;

CATIONIC POLYMERIZATION;

EID: 77951187544     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma100182b     Document Type: Article

References (37)

1. For reviews: (a) Sawamoto, M. Prog. Polym. Sci. 1991, 70, 111-172.
2. (b) Kennedy, J. P.; Ivan, B. Designed Polymers by Carbocationic Macromolecular Engineering: Theory and Practice; Hanser: New York, 1992.
3. (c) Matyjaszewski, K.; Sawamoto, M. In Cationic Polymerizations; Matyjaszewski, K., Ed.; Marcel Dekker: New York, 1996; Chapter 4.
4. (d) Kennedy, J. P. J. Polym. Sci., Part A: Ppolym. Chem. 1993, 37, 2285-2293.
5. (e) Puskas, J. E.; Kaszas, G. Prog. Polym. Sci. 2000, 25, 403-452.
6. (f) De, P.; Faust, R. In Macromolecular Engineering. Precise Synthesis, Materials Properties, Applications.; Matyjaszewski, K.; Gnanou, Y.; Leibler, L., Eds.; WILEY- VCH GmbH & Co. KGaA: Weinheim, Germany, 2007; Chapter 3.
7. (g) Goethals, E. J.; Prez, F. D. Prog. Polym. Sci. 2007, 32, 220-246.
8. (h) Aoshima, S.; Yoshida, T.; Kanazawa, A.; Kanaoka, S. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 1801-1813.
9. (i) Aoshima, S.; Kanaoka, S. Chem. Rev. 2009, 109, 5245-5287.
10. Kanazawa, A.; Kanaoka, S.; Aoshima, S. Mascromolecules 2010, 42, 3965-3972.
11. Kanazawa, A.; Kanaoka, S.; Aoshima, S. Macromolecules 2010, 43, ASAP article.
12. Jones, R. A.; Bean, G. P. The Chemistry of Pyrroles; Academic Press: New York, 1977.
13. (a) Bynum. R. V.; Hunter, W. E.; Rogers, R. D.; Atwood, J. L. Inorg, Chem. 1980, 19, 2368-2374.
14. (b) Fischer, P. J.; Young, V. G., Jr.; Ellis, J. E., Angew. Chem., Int. Ed. 2000, 39, 189-191.
15. (c) Saeed, I.; Katao, S.; Nomura, K. Organometallics 2009, 28, 111-122.
16. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456-463.
17. (a) Jorapur, Y. R.; Lee, C. H.; Chi, D. Y. Org. Lett. 2005, 7, 1231-1234.
18. (b) Palomo, C.; Oiarbide, M.; Kardak, B. G.; Garcia, J. M.; Linden, A. J. Am. Chem. Soc. 2005, 127, 4154-4155.
19. (a) Nigst, T. A.; Westermaier, M.; Ofial, A. R.; Mayr, H. Eur. J. Org. Chem. 2008, 2369-2374.
20. (b) Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66-77.
21. (a) Storey, R. F.; Stokes, C. D.; Harrison, J. J, Macromolecules 2005, 38, 4618-4624.
22. (b) Martinez-Castro, N.; Morgan, D. L.; Storey, R. F. Macromolecules 2009, 42, 4963-4971.
23. (c) Morgan, D. L.; Storey, R. F. Macromolecules 2010, 43, 1329-1340.
24. Higashimura, T.; Kamigaito, M.; Kato, M.; Hasebe, T.; Sawamoto, M. Macromolecules 1993, 26, 2670-2673.
25. Katayama, H.; Kitaguchi, H.; Kamigaito, M.; Sawamoto. M. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 4023-4031.
26. Water was introduced to the system by using water-saturated toluene.
27. Tachikawa, E.; Nishizaki, H.; Kanaoka, S.; Aoshima, S. Polym. Prepr. Jpn. 2007, 56, 259.
28. 13 which implies that the steric effect is not critical.
29. 4.
30. 3 was obtained. Thus, pyrrole-involved structures were likely to exist in larger molecular weight region than those of the observed peaks.
31. The present cationic system may be specific for VEs. No propagation from pyrrole-terminated species would be induced with other monomers such as styrenes and N-vinylcarbazole, since a carbonaryl (C-C) or the carbon-carbazole ring (C-N) bond is difficult to cleave, yielding carbocation, with any Lewis acid.
32. 19 which is conducted in the presence of a transfer agent such as alcohol. The exchange of alcohol (e.g., methanol) with an active polymer chain on the porphyrin occurs frequently in the early stage, yielding a dormant chain. In the propagating reaction, dormant polymer chains (e.g., a polymer with a terminal hydroxy group) and porphyrin-bonded active chains exchange rapidly, in other words, chain transfer occurs continuously throughout the reaction, to realize living polymerization.
33. (a) Asano, S.; Aida, T.; Inoue, S. J. Chem. Soc. Chem. Commun. 1985, 1148-1149.
34. (b) Tneme. S. J. Polym. Sci. Part A: Polym. Chem. 2000, 38, 2861-2871.
35. Aoshima, S.; Higashimura, T. Polym. J. 1984, 16, 249-258.
36. 4. The absorbance of the product polymer at 300 nm was used to compare with these values.
37. Ahmed, F. R.; Toube, T. P. J. Chem. Soc. Perkin Trans. I 1984, 1577-1579.