Copolymerization of amino acid functionalized norbomene monomers. Synthesis of amphiphilic block copolymers forming reverse micelles

Macromolecules

Volumn 41, Issue 2, 2008, Pages 305-311

  Sutthasupa, Sutthira ^a   Sanda, Fumio ^a   Masuda, Toshio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIPHILES; BLOCK COPOLYMERS; HOMOPOLYMERIZATION; MICELLES; MONOMERS;

HYDROPHILIC CORES; HYDROPHOBIC SHELLS; RUTHENIUM CATALYSTS;

AMINO ACIDS;

EID: 38949210634     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma7022233     Document Type: Article

References (35)

1. Biagini, S. C. G.; Coles, M. P.; Gibson, V. C.; Giles, M. R.; Marshall, E. L.; North, M. Polymer 1998, 39, 1007-1014.
2. Maynard, H. D.; Okada, S. Y.; Grubbs, R. H. Macromolecules 2000, 33, 6239-6248.
3. Maynard, H. D.; Okada, S. Y.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 1275-1279.
4. Sanda, F.; Endo, T. Macromol. Chem. Phys. 1999, 200, 2651-2661.
5. Grubbs, R. H.; Tumas, W. Science 1989, 243, 907-915.
6. Schrock, R. R. Acc. Chem. Res. 1990, 23, 158-165.
7. Bazan, G. C.; Shrock, R. R.; Khosravi, E.; Feast, W. J.; Gibson, V. C.; O'Regan, M. B.; Tomas, J. K.; Davis, W. M. J. Am. Chem. Soc. 1990, 112, 8378-8387.
8. Feast, W. J.; Gibson, V. C.; Marshall, E. L. J. Chem. Soc., Chem. Commun. 1992, 1157-1158.
9. Lodge, T. P. Macromol, Chem. Phys. 2003, 204, 265-273.
10. Froster, S.; Plantenberg, T. Angew. Chem., Int. Ed. 2002, 41, 689-714.
11. Hamley, I. W.; Castelletto, V. Prog. Polym. Sci. 2004, 29, 909-948.
12. Gohy, J. F. Adv. Polym. Sci. 2005, 190, 65-136.
13. Rodriguez-Hernandez, J.; Checot, F.; Gnanou, Y.; Lecommandoux, S. Prog. Polym. Sci. 2005, 30, 691-724.
14. Wang, C.; Huang, J.; Tang, S.; Zhu, B. Langmuir 2001, 17, 6389-6392.
15. Xu, H.; Gall, N. L.; Jia, L. ACS Polym. Prepr. 2004, 45 (2), 624-625.
16. Li, B. S.; Cheuk, K. K. L.; Yang, D.; Lam, J. W. Y.; Wan, L. J.; Bai, C.; Tang, B. Z. Macromolecules 2003, 36, 5447-5450.
17. Ahmed, S. R.; Bullock, S. E.; Cresce, A. V.; Kofinas, P. Polymer 2003, 44, 4943-4948.
18. Ahmed, S. R.; Kofinas, P. Macromolecules 2002, 35, 3338-3341.
19. Saunders, R. S.; Cohen, R. E.; Wong, S. J.; Schrock, R. R. Macromolecules 1992, 25, 2055-2057.
20. Stubenrauch, K.; Moitzi, C.; Fritz, G.; Glatter, O.; Trimmel, G.; Stelzer, F. Macromolecules 2006, 39, 5865-5874.
21. Sutthasupa, S.; Terada, K.; Sanda, F.; Masuda, T. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 5337-5343.
22. Sutthasupa, S.; Terada, K.; Sanda, F.; Masuda, T. Polymer 2007, 48, 3026-3032.
23. Kiessling, L. L.; Owen, R. M. In In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; Vol. 3; Chapter 3.6.
24. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
25. Choi, T-L.; Grubbs, R. H. Angew. Chem., Int. Ed. 2003, 42, 1743-1746.
26. Romero, P. E.; Piers, W. E.; Mcdonald, R. Angew. Chem., Int. Ed. 2004, 43, 6161-6165.
27. We polymerized monomer 1 first and then 2 in the synthesis of block copolymers, because we thought that the carboxylic acid moieties of monomer 2 might interact with the catalyst to retard the polymerization as described in the Introduction. If this occurs, the order in the present study is better than that of 2 first and then 1 for obtaining the block copolymer more efficiently, because the quantitative conversion of the first monomer is important. In fact, the rate of polymerization of monomer 1 was higher than that of 2 (see Supporting Information).
28. 6, we could determine the H/D exchange rate and discuss the possibility much more.
29. Bakshi, M. S.; Singh, J.; Singh, K.; Kaur, G. Colloids Surf. A: Physicochem. Eng. Asp. 2004, 237, 61-71.
30. Zhang, J. X.; Qiu, L. Y.; Jin, Y.; Zhu, K. J. Colloids Surf. B: Biointerfaces 2005, 43, 123-130.
31. Huang, C. J.; Shieu, F. S. Colloid Polym. Sci. 2005, 284, 192-202.
32. Halacheva, S.; Rangelov, S.; Tsvetanov, C. Macromolecules 2006, 39, 6845-6852.
33. Lee, E. S.; Shin, H. J.; Na, K.; Bae, Y. H. J. Controlled Release 2003, 90, 363-374.
34. Hamley, I. W. In Introduction to Soft Matter: Polymers, Colloids, Amphiphiles and Liquid Crystals; Wiley-VCH: Weinheim, Germany, 2000; Chapter 4.6, page 217.
35. Liaw, D. J.; Huang, C. C.; Kang, E. T. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 2901-2911.