New ring-opening polymerization via a π-allylpalladium complex. 5. Multibranching polymerization of cyclic carbamate to produce hyperbranched dendritic polyamine

Macromolecules

Volumn 31, Issue 6, 1998, Pages 1716-1719

  Suzuki, Masato ^a   Yoshida, Satoshi ^b   Shiraga, Koichi ^b   Saegusa, Takeo ^b,c  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c Kyoto Research Park ^*  (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CHEMICAL ACTIVATION; COMPOSITION EFFECTS; INITIATORS (CHEMICAL); MOLECULAR STRUCTURE; MONOMERS; PALLADIUM COMPOUNDS; PROTONS; RING OPENING POLYMERIZATION;

ALLYLPALLADIUM COMPLEX; CYCLIC CARBAMATE; POLYAMINE;

AROMATIC POLYMERS;

EID: 0032024760     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma971222t     Document Type: Article

References (21)

1. Suzuki, M.; Ii, A.; Saegusa, T. Macromolecules 1992, 25, 7071.
2. Suzuki, M.; Ito, H.; Saegusa, T. Polym. Prepr. Jpn. 1993, 42, 376. The paper is in preparation.
3. A review: Bochkarev, M. N.; Katkova, M. A. Usp. Khim. 1995, 64, 1106; Russ. Chem. Rev. 1995, 64, 1035 (Engl. Transl.). Hawker, C. J.; Chu, F. Macromolecules 1996, 29, 4370 and references therein.
4. A review: Bochkarev, M. N.; Katkova, M. A. Usp. Khim. 1995, 64, 1106; Russ. Chem. Rev. 1995, 64, 1035 (Engl. Transl.). Hawker, C. J.; Chu, F. Macromolecules 1996, 29, 4370 and references therein.
5. A review: Bochkarev, M. N.; Katkova, M. A. Usp. Khim. 1995, 64, 1106; Russ. Chem. Rev. 1995, 64, 1035 (Engl. Transl.). Hawker, C. J.; Chu, F. Macromolecules 1996, 29, 4370 and references therein.
6. A very recent paper proposed a method to improve this problem by use of a solid support: Bharathi, P.; Moore, J. S. J. Am. Chem. Soc. 1997, 119, 3391.
7. Fréchet, J. M. J.; Henmi, M.; Gitsov, I.; Aoshima, S.; Leduc, M.; Grubbs, R. B. Science 1995, 269, 1080. Hawker, C, J.; Fréchet, J. M. J.; Grubbs, R. B.; Dao, J. J. Am. Chem. Soc. 1995, 117, 10763. Gaynor, S. G.; Edelman, S.; Matyjaszewski, K. Macromolecules 1996, 29, 1079.
8. Fréchet, J. M. J.; Henmi, M.; Gitsov, I.; Aoshima, S.; Leduc, M.; Grubbs, R. B. Science 1995, 269, 1080. Hawker, C, J.; Fréchet, J. M. J.; Grubbs, R. B.; Dao, J. J. Am. Chem. Soc. 1995, 117, 10763. Gaynor, S. G.; Edelman, S.; Matyjaszewski, K. Macromolecules 1996, 29, 1079.
9. Fréchet, J. M. J.; Henmi, M.; Gitsov, I.; Aoshima, S.; Leduc, M.; Grubbs, R. B. Science 1995, 269, 1080. Hawker, C, J.; Fréchet, J. M. J.; Grubbs, R. B.; Dao, J. J. Am. Chem. Soc. 1995, 117, 10763. Gaynor, S. G.; Edelman, S.; Matyjaszewski, K. Macromolecules 1996, 29, 1079.
10. Reviews: Tomalia, D. A.; Naylor, A. D.; Goddard, W. A., III Angew. Chem., Int. Ed. Engl. 1990, 29, 138. Issberner, J.; Moors, R.; Vögtle, F. Ibid. 1994, 33, 2413. Tomalia, D. A. Macromol Symp. 1996, 101, 243. Hawker, C. J.; Fréchet, J. M. J. New Methods Polym. Synth. 1995, 290. Fréchet, J. M. J.; Hawker, C. J.; Gitsov, I.; Leon, J. W. J. Macromol. Sci., Pure Appl. Chem. 1996, A33, 1399.
11. Reviews: Tomalia, D. A.; Naylor, A. D.; Goddard, W. A., III Angew. Chem., Int. Ed. Engl. 1990, 29, 138. Issberner, J.; Moors, R.; Vögtle, F. Ibid. 1994, 33, 2413. Tomalia, D. A. Macromol Symp. 1996, 101, 243. Hawker, C. J.; Fréchet, J. M. J. New Methods Polym. Synth. 1995, 290. Fréchet, J. M. J.; Hawker, C. J.; Gitsov, I.; Leon, J. W. J. Macromol. Sci., Pure Appl. Chem. 1996, A33, 1399.
12. Reviews: Tomalia, D. A.; Naylor, A. D.; Goddard, W. A., III Angew. Chem., Int. Ed. Engl. 1990, 29, 138. Issberner, J.; Moors, R.; Vögtle, F. Ibid. 1994, 33, 2413. Tomalia, D. A. Macromol Symp. 1996, 101, 243. Hawker, C. J.; Fréchet, J. M. J. New Methods Polym. Synth. 1995, 290. Fréchet, J. M. J.; Hawker, C. J.; Gitsov, I.; Leon, J. W. J. Macromol. Sci., Pure Appl. Chem. 1996, A33, 1399.
13. Reviews: Tomalia, D. A.; Naylor, A. D.; Goddard, W. A., III Angew. Chem., Int. Ed. Engl. 1990, 29, 138. Issberner, J.; Moors, R.; Vögtle, F. Ibid. 1994, 33, 2413. Tomalia, D. A. Macromol Symp. 1996, 101, 243. Hawker, C. J.; Fréchet, J. M. J. New Methods Polym. Synth. 1995, 290. Fréchet, J. M. J.; Hawker, C. J.; Gitsov, I.; Leon, J. W. J. Macromol. Sci., Pure Appl. Chem. 1996, A33, 1399.
14. Reviews: Tomalia, D. A.; Naylor, A. D.; Goddard, W. A., III Angew. Chem., Int. Ed. Engl. 1990, 29, 138. Issberner, J.; Moors, R.; Vögtle, F. Ibid. 1994, 33, 2413. Tomalia, D. A. Macromol Symp. 1996, 101, 243. Hawker, C. J.; Fréchet, J. M. J. New Methods Polym. Synth. 1995, 290. Fréchet, J. M. J.; Hawker, C. J.; Gitsov, I.; Leon, J. W. J. Macromol. Sci., Pure Appl. Chem. 1996, A33, 1399.
15. Suzuki, M.; Sawada, S.; Saegusa, T. Macromolecules 1989, 22, 1505. Suzuki, M.; Sawada, S.; Yoshida, S.; Eberhardt, A.; Saegusa, T. Macromolecules 1993, 26, 4748. Suzuki, M.; Haruyama, T.; Ii, A.; Saegusa, T. Polym. Bull. 1996, 36, 265.
16. Suzuki, M.; Sawada, S.; Saegusa, T. Macromolecules 1989, 22, 1505. Suzuki, M.; Sawada, S.; Yoshida, S.; Eberhardt, A.; Saegusa, T. Macromolecules 1993, 26, 4748. Suzuki, M.; Haruyama, T.; Ii, A.; Saegusa, T. Polym. Bull. 1996, 36, 265.
17. Suzuki, M.; Sawada, S.; Saegusa, T. Macromolecules 1989, 22, 1505. Suzuki, M.; Sawada, S.; Yoshida, S.; Eberhardt, A.; Saegusa, T. Macromolecules 1993, 26, 4748. Suzuki, M.; Haruyama, T.; Ii, A.; Saegusa, T. Polym. Bull. 1996, 36, 265.
18. Ukai, T.; Kawazura, H.; Ishii, Y. J. Organomet. Chem. 1974, 65, 253.
19. 3P. This is ascribable to the steric and electronic difference between two π-allylpalladium intermediates generated respectively from 1 and 2; one is vinylic and the other is exomethylenic (see the mechanism).
20. This phenomenon was observed also on the polymer produced from 1. Generally, polyamine sometimes shows this character. This is possibly due to complex entanglement accompanied by intermolecular hydrogen bonds at many points of the polymer chains.
21. j. As a result, a DB value is given by this equation.