Metal-free catalyzed ring-opening polymerization of β-lactones: Synthesis of amphiphilic triblock copolymers based on poly(dimethylmalic acid)

Macromolecules

Volumn 39, Issue 12, 2006, Pages 4001-4008

  Coulembier, Olivier ^a   Mespouille, Laetitia ^a   Hedrick, James L ^b   Waymouth, Robert M ^c   Dubois, Philippe ^a  

^a UNIVERSITY OF MONS   (Belgium)

^b IBM ALMADEN RESEARCH CENTER   (United States)

^c STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIPHILIC TRIBLOCK COPOLYMERS; DIMETHYL BENZYL; ETHYLENE GLYCOL; GEL-SOL TRANSITION;

CATALYSTS; GELATION; GLYCOLS; HYDROGENATION; INITIATORS (CHEMICAL); NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHASE DIAGRAMS; RING OPENING POLYMERIZATION; SOL-GELS; SOLVENTS; SYNTHESIS (CHEMICAL); TOLUENE;

COPOLYMERS;

EID: 33745792993     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma060552n     Document Type: Article

References (60)

1. Pitt, C. G.; Gratzl, M. M.; Himmel, G. L.; Surles, J.; Schindler, A. Biomaterials 1981, 2, 215.
2. Kaetsu, I.; Yoshida, M.; Asano, M.; Yamanaka, H.; Imai, K.; Yuasa, H.; Mashimo, T.; Susuki, K.; Katakai, R.; Oya, M. J. Controlled Release 1987, 6, 249.
3. Fitzgerald, J. F.; Corrigan, O. I. J. Controlled Release 1996, 42, 125.
4. Schakenraad, J. M.; Oosterbaan, J. A.; Nieuwenhuis, P.; Molenaar, I.; Olijslager, J.; Potman, W.; Eenink, M. J. D.; Feijen, J. Biomaterials 1988, 9, 116.
5. Sanders, L. M.; Kent, J. S.; McRae, G. I.; Vickery, B. H.; Tice, T. M.; Lewis, D. H. J. Pharm. Sci. 1984, 73, 1294.
6. Arshady, R. J. Bioact. Compat. Polym. 1990, 5, 315.
7. Kyo, M.; Hyon, S. H.; Ikada, Y. J. Controlled Release 1995, 35, 73.
8. Takada, S.; Uda, Y.; Toguchi, H.; Ogawa, Y. J. Pharm. Sci. Technol. 1995, 49, 180.
9. Li, S.; Vert, M. In The Encyclopedia of Controlled Drug Delivery; Mathiowitz, E., Ed.; Wiley & Sons: New York, 1999, p 71.
10. Hoffman, A. S. Adv. Drug Delivery Rev. 2002, 54, 3.
11. Dunn, R. L. In Biomedical Applications of Synthetic Biodegradable Polymers; Hollinger, J. O., Ed.; CRC Press: Boca Raton, FL, 1995; p 17.
12. Li, S. J. Biomed. Mater. Res. 1999, 48, 342.
13. Ouhib, F.; Randriamahefa, S.; Guérin, Ph.; Barbaud, Ch. Des. Monomers Polym. 2005, 1, 25.
14. Magee, P. T.; Snell, E. E. Biochemistry 1966, 5, 409.
15. (a) Ovitt, T. M.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 4072.
16. (b) O'Keefe, B. J.; Hillmyer, M. A.; Tolman, W. B. J. Chem. Soc., Dalton Trans. 2001, 15, 2215.
17. (c) Dechy-Cabaret, O.; Martin-Vaca, B.; Bourissou, D. Chem. Rev. 2004, 104, 6147.
18. (d) Wu, J.; Yu, T.-L.; Chen, C.-T.; Lin, C.-C. Coord. Chem. Rev. 2006, 205, 602.
19. (e) Hadjichristidis, N.; Pitskalis, M.; Pispas, S.; Latrou, H. Chem. Rev. 2001, 101, 3747.
20. (f) Coulembier, O.; Degée, Ph.; Hedrick, J. L.; Dubois, Ph. Prog. Polym. Sci. 2006, submitted.
21. (a) Borman, S. Chem. Eng. News 2002, 80, 33.
22. (b) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894.
23. (c) Hodous, B. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 1578.
24. (d) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F. J. Am. Chem. Soc. 2002, 124, 1842.
25. (e) Wang, L.; Luis, L. A.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402.
26. (f) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243.
27. (g) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874-9875.
28. (h) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370-4371.
29. (i) Fu, G. C. Acc. Chem. Res. 2000, 33, 412-420.
30. (j) Arai, S.; Bellemin-Laponnaz, S.; Fu, G. C. Angew. Chem., Int. Ed. 2001, 40, 234.
31. (k) Dong, V. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 113, 240.
32. (l) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874.
33. (m) Nederberg, F.; Connor, E. F.; Glauser, T.; Hedrick, J. L. Chem. Commun. 2001, 2066.
34. (n) List, B.; Lerner, R. A.; Barbas, C. A. J. Am. Chem. Soc. 2000, 122, 2395.
35. (o) Myers, M.; Connor, E.; Nyce, G.; Glauser, T.; Mock, A.; Hedrick, J. L. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 844.
36. For example, see: (a) Nyce, G. W.; Lamboy, J. A.; Connor, E. F.; Waymouth, R. M.; Hedrick, J. L. Org. Lett. 2002, 4, 3587.
37. (b) Grasa, G. A.; Kissling, R. M.; Nolan, S. P. Org. Lett. 2002, 4, 3583.
38. (c) Wanzlick, H. W.; Kleiner, H. J. Angew. Chem., Int. Ed. Engl. 1997, 73, 4493.
39. (d) Denk, M. K.; Thadani, A.; Hatano, K.; Lough, A. J. Angew. Chem., Int. Ed. Engl. 1997, 109, 2719.
40. (e) Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. 1995, 34, 1021.
41. (f) Kerr, M. S.; De Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298.
42. (g) Chow, K. Y. K.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 8126.
43. (h) Reynolds, N. T.; de Alaniz, J. R.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518.
44. (i) Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370.
45. (a) Nederberg, F.; Connor, E. F.; Moller, M.; Glauser, T.; Hedrick, J. L. Angew. Chem., Int. Ed. 2001, 40, 2712.
46. (b) Nyce, G. W.; Glauser, Th.; Connor, E. F.; Mock, A.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2003, 125, 3046.
47. (c) Nyce, G. W.; Csihony, S.; Waymouth, R. M.; Hedrick, J. L. Chem.-Eur. J. 2004, 10, 4073.
48. (d) Csihony, S.; Sentman, A. C.; Dove, A. P.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2005, 127, 9079.
49. (e) Coulembier, O.; Dove, A. P.; Pratt, R. C.; Sentman, A. C.; Culkin, D. A.; Mespouille, L.; Dubois, Ph.; Waymouth, R. M.; Hedrick, J. L. Angew. Chem., Int. Ed. Engl. 2005, 44, 4964.
50. (f) Coulembier, O.; Lohmeijer, B. G. G.; Dove, A. P.; Pratt, R. C.; Culkin, D. A.; Mespouille, L.; Dubois, Ph.; Waymouth, R. M.; Hedrick, J. L. Macromolecules, submitted for publication.
51. Gross, R. A.; Williams, S. J. J. Chem. Soc., Chem. Commun. 1995, 12, 1267.
52. Fineman, M.; Ross, S. D. J. Polym. Sci. 1950, 5, 259.
53. See for example: (a) Wanzlick, H. W.; Ahrens, H. Chem. Ber. 1966, 99, 1580.
54. (b) Wanzlick, H. W.; Kleiner, A. Chem. Ber. 1963, 96, 3024.
55. (c) Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Liebigs Ann. 1996, 2019.
56. Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem. 1995, 107, 1119.
57. Coulembier, O.; Degée, Ph.; Cammas-Marion, S.; Guérin, Ph.; Dubois, Ph. Macromolecules 2002, 35, 9896.
58. Jeong, B.; Lee, D. S.; Shon, J.; Bae, Y. H.; Kim, S. W. J. Polym. Sci., Part A 1999, 37, 751.
59. Malmsten, M.; Lindman, B. Macromolecules 1992, 25, 5440.
60. Lee, D. S.; Shim, M. S.; Kim, S. W.; Lee, H.; Park, I.; Chang, T. Macromol. Rapid Commun. 2001, 22, 587.