Use of ascorbic acid as reducing agent for synthesis of well-defined polymers by ARGET ATRP

Macromolecules

Volumn 40, Issue 6, 2007, Pages 1789-1791

  Min, Ke ^a   Gao, Haifeng ^a   Matyjaszewski, Krzysztof ^a  

^a CARNEGIE MELLON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASCORBIC ACID; HOMOGENEOUS REACTION; N,N-DIMETHYLFORMAMIDE (DMF);

AMINES; ATOM TRANSFER RADICAL POLYMERIZATION; ELECTRON TRANSITIONS; REDUCING AGENTS; SOLUBILITY; SYNTHESIS (CHEMICAL);

CARBOXYLIC ACIDS;

EID: 33947693699     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma0702041     Document Type: Article

References (36)

1. Wang, J.-S.: Matyjaszewski, K. J. Am. Chem. Soc. 1995, 117, 5614-5615.
2. Kato, M.; Kamigaito, M.; Sawamoto, M.: Higashimura. T. Macromolecules 1995, 28, 1721-1723.
3. Matyjaszewski, K.; Xia, J. Chem. Rev. 2001, 101, 2921-2990.
4. Gao, H.: Tsarevsky, N. V.; Matyjaszewski, K. Macromolecules 2005, 38, 5995-6004.
5. Davis, K. A.; Matyjaszewski, K. Adv. Polym. Sci. 2002, 159, 1-166.
6. Coessens, V.: Pintauer, T.; Matyjaszewski, K. Prog. Polym. Sci. 2001, 26, 337-377.
7. Edmondson, S.; Osborne. V. L.; Huck. W. T. S. Chem. Soc. Rev. 2004, 33, 14-22.
8. Pyun, J.; Kowalewski, T.; Matyjaszewski, K. Macromol. Rapid Commun. 2003, 24, 1043-1059.
9. von Werne, T.; Patten. T. E. J. Am. Chem. Soc. 2001, 123, 7497-7505.
10. Yu, W. H.; Kang, E. T.; Neoh, K. G.: Zhu, S. J. Phys. Chem. B 2003, 107, 10198-10205.
11. Kong, H.;Gao. C.; Van, D. J. Am. Chem. Soc. 2004, 126, 412-413.
12. Becker, M. L.; Liu, J.: Wooley, K. L. Biomacromolecules 2005, 6, 220-228.
13. Ohno, K.; Morinaga, T.; Koh, K.; Tsujii. Y.; Fukuda, T. Macromolecules 2005, 38, 2137-2142.
14. Cai, Q. J.; Fu, G. D.; Zhu. F. R.; Kang, E.-T.: Neoh, K.-G. Angew. Chem., Int. Ed. 2005, 44, 1104-1107.
15. Li. D.; Jones, G. L.: Dunlap. J. R.; Hua. F.; Zhao. B. Langmuir 2006, 22, 3344-3351.
16. Azzaroni, O.: Brown, A. A.; Huck. W. T. S. Angew. Chem., Int. Ed. 2006, 45, 1770-1774.
17. Licciardi, M.; Tang, Y.; Billingham, N. C.; Armes, S. P.; Lewis. A. L. Biomacromolecules 2005, 6, 1085-1096.
18. Bontempo, D.; Heredia, K. L.; Fish, B. A.; Maynard, H. D. J. Am. Chem. Soc. 2004, 126, 15372-15373.
19. Mei, Y.; Beers, K. L.; Byrd, H. C. M.; VanderHart, D. L.; Washburn, N. R. J. Am. Chem. Soc. 2004, 126, 3472-3476.
20. Tao, L.; Mantovani, G.; Lecolley, F.; Haddleton, D. M. J. Am. Chem. Soc. 2004, 126, 13220-13221.
21. Bontempo, D.; Li Ronald, C.; Ly, T.; Brubaker, C. E.; Maynard, H. D. Chem. Commun. 2005, 4702-4704.
22. Heredia, K. L.; Bontempo, D.; Ly, T.; Byers, J. T.; Halstenberg, S.; Maynard, H. D. J. Am. Chem. Soc. 2005, 127, 16955-16960.
23. Sen Gupta, S.; Raja, K. S.; Kaltgrad, E.; Strahle, E.; Finn, M. G. Chem. Commun. 2005, 4315-4317.
24. Chen, G.; Huynh, D.; Felgner, P. L.; Guan, Z. J. Am. Chem. Soc. 2006, 128, 4298-4302.
25. Min, K.; Gao, H.; Matyjaszewski, K. J. Am. Chem. Soc. 2005, 127, 3825-3830.
26. Jakubowski, W.; Matyjaszewski, K. Macromolecules 2005, 38, 4139-4146.
27. Jakubowski, W.; Min, K.; Matyjaszewski, K. Macromolecules 2006. 39, 39-45.
28. Jakubowski, W.; Matyjaszewski, K. Angew. Chem. 2006, 118, 4594-4598.
29. Matyjaszewski, K.; Jakubowski, W.; Min, K.; Tang, W.; Huang, J.; Braunecker, W. A.; Tsarevsky, N. V. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 15309-15314.
30. Min, K.; Matyjaszewski, K. Macromolecules 2005, 38, 8131-8134.
31. Hizal, G.; Tunca, U.; Aras, S.; Mert, H. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 77-87.
32. Min, K.; Jakubowski, W.; Matyjaszewski, K. Macromol Rapid Commun. 2006, 27, 594-598.
33. Min, K.; Gao, H.; Matyjaszewski, K. J. Am. Chem. Soc. 2006, 128, 10521-10526.
34. Oh, J. K.; Tang, C.; Gao, H.; Tsarevsky, N. V.; Matyjaszewski, K. J. Am. Chem. Soc. 2006, 128, 5578-5584.
35. A precise solubility of ascorbic acid in the reaction mixture is difficult to determine because the solubility is extremely low, and it varies with temperature, monomer concentration, and monomer conversion during polymerization. The solubility of ascorbic acid in anisole was qualitatively evaluated by mixing 5 mg of ascorbic acid and 500 mL of anisole. After stirring the mixture for 24 hours at RT, the insoluble solid ascorbic acid powder was clearly observed. Based on the observation, the solubility of ascorbic acid in anisole at RT should be lower than 1.0 mg/100 mL.
36. Percec, V.; Guliashvili, T.; Ladislaw, J. S.; Wistrand, A.; Stjerndahl, A.; Sienkowska, M. J.; Monteiro, M. J.; Sahoo, S. J. Am. Chem. Soc. 2006, 128, 14156-14165.