Organocatalytic ring opening polymerization of trimethylene carbonate

Biomacromolecules

Volumn 8, Issue 1, 2007, Pages 153-160

  Nederberg, Fredrik ^a,b   Lohmeijer, Bas G G ^a,b   Leibfarth, Frank ^a   Pratt, Russell C ^a   Choi, Jeongsoo ^a   Dove, Andrew P ^c   Waymouth, Robert M ^b   Hedrick, James L ^a  

^a IBM ALMADEN RESEARCH CENTER   (United States)

^b UNIVERSITY OF WARWICK   (United Kingdom)

^c STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIFUNCTIONAL INITIATORS; ORGANOCATALYSTS; POLYDISPERSITIES; TRIMETHYLENE CARBONATE;

BLOCK COPOLYMERS; MOLECULAR WEIGHT; MONOMERS; POLYCARBONATES;

RING OPENING POLYMERIZATION;

1,3 BIS(2,6 DIISOPROPYLPHENYL)IMIDAZOL 2 YLIDENE; 1,3 DIISOPROPYL 4,5 DIMETHYLIMIDAZOL 2 YLIDENE; 1,5,7 TRIAZABICYCLO[4.4.0]DEC 5 ENE; 1,8 DIAZABICYCLO[5.4.0]UNDEC 7 ENE; 7 METHYL 1,5,7 TRIAZABICYCLO[4.4.0]DEC 5 ENE; AMIDINE; CARBENOID; CARBONIC ACID DERIVATIVE; COPOLYMER; CYCLOPROPANE DERIVATIVE; GUANIDINE DERIVATIVE; MONOMER; POLYCARBONATE; THIOUREA DERIVATIVE; TRIMETHYLENE CARBONATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL PROCEDURES; CHEMICAL REACTION; CONTROLLED STUDY; DISPERSION; HYDROGEN BOND; MOLECULAR WEIGHT; POLYMERIZATION; PRIORITY JOURNAL; RING OPENING; RING OPENING POLYMERIZATION;

BIOCHEMISTRY; CATALYSIS; CHEMISTRY, ANALYTICAL; DIOXANES; HYDROGEN BONDING; MACROMOLECULAR SUBSTANCES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR CONFORMATION; POLYMERS; TEMPERATURE; TIME FACTORS;

EID: 33846413167     PISSN: 15257797     EISSN: None     Source Type: Journal    
DOI: 10.1021/bm060795n     Document Type: Article

References (82)

1. (a) Andronova, N.; Albertsson, A. C. Biomacromolecules 2006, 7, 1489.
2. (b) Kricheldorf, H. R.; Rost, S. Macromolecules 2005, 38, 8220.
3. (c) Feng, J.; He, F.; Zhuo, R. Macromolecules 2002, 35, 7175.
4. (d) Kim, C.; Lee, S. C.; Shin, J. H.; Yoon, J. S. Macromolecules 2000, 33, 7448-7452.
5. (e) Al-Azemi, T. F.; Harmon, J. P.; Bisht, K. S. Biomacromolecules 2000, 1, 493.
6. Rokicki, G. Prog. Polym. Sci. 2000, 25, 259-342.
7. (a) Kricheldorf, H. R.; Dunsing, R.; Serra, A. Makromol. Chem 1987, 188, 2453.
8. (b) Albertsson, A.-C.; Sjoeling, M. J. Macromol. Sci., Pure Appl. Chem. 1992, 29, 43.
9. (c) Ariga, T.; Takata, T.; Endo, T. Macromolecules 1997, 30, 737.
10. (a) Keul, H.; Baecher, R.; Hoecker, H. Makromol. Chem. 1986, 187, 2579.
11. (b) Matsuo, J.; Aoki, K.; Sanda, F.; Endo, T. Macromolecules 1998, 31, 4432.
12. (a) Kricheldorf, H. R.; Jenssen, J.; Kreiser-Sanders, I. Makromol. Chem. 1992, 2391.
13. (b) Carter, K. R.; Richter, R.; Kricheldorf, H. R.; Hedrick, J. L. Macromolecules 1997, 30, 6074.
14. (c) Dobrzynski, P.; Kasperczyk, J. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 3184.
15. (a) Bisht, K. S.; Svirkin, Y. Y.; Henderson, L. A.; Gross, R. A.; Kaplan, D. L.; Swik G. Macromolecules 1997, 30, 7735.
16. (b) Kricheldorf, H. R.; Lee, S.-R.; Weegen-Schulz, B. Macromol. Chem. Phys. 1996, 197, 1043.
17. (c) Varma, I. K.; Albertsson, A.-C.; Rajkhowa, R.; Srivastava, R. K. Prog. Polym. Sci. 2005, 30, 949.
18. Darensbourg, D. J.; Choi, W.; Ganguly, P.; Richers, C. P. Macromolecules 2006, 39, 4374.
19. Hermans, T. M.; Choi, J.; Lohmeijer, B. G. G.; Dubois, G.; Pratt, R. C.; Kim, H.-C.; Waymouth, R. M.; Hedrick, J. L. Angew. Chem, Int. Ed. 2006, in press.
20. Nederberg, F.; Connor, E. F.; Moeller, M.; Glausser, T.; Hedrick, J. L. Angew. Chem., Int. Ed. 2001, 40, 2712.
21. Myers, M.; Connor, E. F.; Glausser, T.; Moeck, A.; Nyce, G. W.; Hedrick, J. L. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 844.
22. (a) Connor, E. F.; Nyce, G. W.; Myers, M.; Moeck, A.; Hedrick, L. J. Am Chem. Soc. 2002, 124, 914.
23. (b) Coulembier, O.; Dove, A. P.; Pratt, R. C.; Sentman, A. C.; Culkin, D. A.; Mespouille, L.; Dubois, P.; Waymouth, R. M.; Hedrick, J. L. Angew. Chem, Int. Ed. 2005, 44, 4964.
24. (c) Dove, A. P.; Pratt, R. C.; Lohmeijer, B. G. G.; Culkin, D. A.; Hagberg, E. C.; Nyce, G. W.; Waymouth, R. M.; Hedrick, J. L. Polymer 2006, 47, 4018.
25. Dove, A. P.; Pratt, R. C.; Lohmeijer, B. G. G.; Waymouth, R. M.; Hedrick, J. L. J. Am Chem. Soc. 2005, 127, 13798.
26. Pratt, R. C.; Lohmeijer, B. G. G.; Long, D. A.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem Soc. 2006, 128, 4556.
27. Lohmeijer, B. G. G.; Dubois, G.; Leibfarth, F.; Nederberg, F.; Pratt, R. C.; Nelson, A.; Choi, J.; Wade, C.; Waymouth. R. M., Hedrick, J. L. Org. Lett. 2006, in press.
28. (a) Schreiner, P. R.; Chem Soc. Rev. 2003, 32, 289.
29. (b) Taylor, M. S.; Jacobsen, E. N. Angew. Chem, Int. Ed. 2006, 45, 1520.
30. (c) Marigo, M.; Jørgensen, K. A. Chem Commun. 2006, 2001.
31. Kaljurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I. A. J. Org. Chem 2005, 70, 1019.
32. Magill, A. M.; Cacell, K. J.; Yates, B. F. J. Am. Chem. Soc. 2004 126, 8717.
33. (a) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279.
34. (b) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
35. (c) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.
36. (d) Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 10558.
37. (e) Joly, G. D.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 4102.
38. (f) Fuerst, D. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127, 8964.
39. (g) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672.
40. (h) Okino, T.; Nakamura, S.; Furukawa, T.; Takemoto, Y. Org. Lett. 2004, 6, 625.
41. (i) Hoashi, Y.; Okino, T.; Takemoto, Y. Angew. Chem, Int. Ed. 2005 44, 4100.
42. (j) Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. J. Am Chem Soc. 2005, 127, 199.
43. (k) Berkessel, A.; Mukherjee, S.; Cleemann, F.; Muller, T. N.; Lex, J. Chem. Commun. 2005, 1898.
44. (l) Berkessel, A.; Mukherjee, S.; Cleemann, F.; Muller, T. N.; Lex J. Angew. Chem, Int. Ed. 2005, 44, 807.
45. Zhang, Z.; Zou, S.; Vancso, G. J.; Grijpma, D. W.; Feijen, J. Biomacromolecules 2005, 6, 3404.
46. (a) Pego, A. P.; Zhong, Z.; Dijkstra, P. J.; Grijpma, D. W.; Feijen J. Macromol. Chem. Phys. 2003, 204, 747.
47. (b) Kricheldorf, H. R.; Stricker, A. Macromol. Chem. Phys. 1999, 200, 1726.
48. (c) Albertsson, A. C.; Eklund, M. J. Polym. Sci., Part A: Polym. Chem 1994, 32, 265.
49. Kricheldorf, H. R. Makromol. Chem. 1979, 2133.
50. Fox, T. G. Bull. Am. Phys. Soc. 1956, 1, 123.
51. (a) Matyjaszewski, K.; Xia, J. Chem. Rev. 2001, 101, 2921.
52. (b) Hawker, C. J.; Bosman, A. W.; Harth, E. Chem. Rev. 2001, 101 3661.
53. (c) Kamigaito, M.; Ando, T.; Sawamoto, M. Chem. Rev. 2001, 101, 3689.
54. (d) Moad, G.; Thang, S. H.; Rizzardo, E. Aust. J. Chem. 2005, 58, 379.
55. (a) Bosman, A. W.; Vestberg, R.; Heumann, A.; Frechet, J. M. J.; Hawker, C. J. J. Am. Chem. Soc. 2003, 125, 715.
56. (b) Thang, S. H.; Chong, Y. K.; Mayadunne, R. T. A.; Moad, G.; Rizzardo, E. Tetrahedron Lett. 1999, 40, 2435.
57. Benoit, D.; Chaplinski, V.; Breslau, R.; Hawker, C. J. J. Am. Chem. Soc. 1999, 121, 3904.
58. (a) Le, T. P. T.; Moad, G.; Rizzardo, E.; Thang, S. H. PCT Int. WO 98/ 01478.
59. (b) Chiefari, J.; Chong, Y. K.; Ercole, F.; Krstina, J Jeffery, J.; Le, T. P. T.; Mayadunne, R. T. A.; Meijs, G. F.; Moad, C. L.; Moad, G.; Rizzardo, E.; Thang, S. H. Macromolecules 1998 31, 5559.
60. (c) Convertine, A. J.; Sumerlin, B. S.; Thomas, D. B.; Lowe, A. B.; McCormick, C. L. Macromolecules 2003, 36, 4679.
61. (d) McCormick, C. L.; Lowe, A. B. Acc. Chem. Res. 2004, 37, 312.
62. (a) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719.
63. (b) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298.
64. (c) Enders, D.; Kallfass, U. Angew. Chem, Int. Ed. 2002, 41, 1743.
65. (d) Teles, J.; Melder, J.; Ebel, K.; Enders, D.; Breuer, J. H. Helv. Chim. Acta 1996, 79, 61.
66. (e) Grasa, G. A.; Kissling, R. M.; Nolan, S. P. Org. Lett. 2002, 4, 3583.
67. (f) Nyce, G. W.; Lamboy, J. A.; Connors, E. F.; Waymouth, R. M.; Hedrick. J. L. Org. Lett. 2002, 4, 3587.
68. Movassaghi, M.; Schmidt, M. A. Org. Lett. 2005, 7, 2453.
69. Kaljurand, I.; Roodima, T.; Pihl, A.; Mäemets, V.; Leito, I.; Koppel, I. A.; Mishima, M. J. Org. Chem. 2003, 68, 9988.
70. Boczon, W.; Jasiewicz, B. Collect. Czech. Chem. Commun. 2003, 68, 696.
71. (a) connors, K. A. Binding Constants: The Measurement of Molecular Complex Stability; Wiley-Interscience: New York, 1987; Ch. 5, pp 189-215.
72. (b) Bisson, A. P.; Hunter, C. A.; Morales, J. C.; Young, K. Chem. - Eur. J. 1998, 4, 845.
73. (c) The program was downloaded from http://www.chris-hunter.staff.shef.ac.uk/soft.html.
74. Lohmeijer, B. G. G.; Pratt, R. C.; Leibfarth, F.; Logan, J. W.; Long, D. A.; Dove, A. P.; Nederberg, F.; Choi, J.; Waymouth, R. M.; Hedrick, J. L., manuscript submitted.
75. Kuhn, N.; Kratz, T. Synthesis 1993, 561.
76. Arduengo, A. J., III; Krafczyk, R.; Schmutzler, R.; Craig, H.; Goerlich, J. R.; Marshall. W. J.; Unverzagt, M. Tetrahedron 1999, 55, 14523.
77. Bosman, A. W.; Vestberg, R.; Heumann, A.; Frechet, J. M. J.; Hawker, C. J. J. Am. Chem. Soc. 2003, 125, 715.
78. Thang, S. H.; Chong, Y. K.; Mayadunne, R. T. A.; Moad. G.; Rizzardo, E. Tetrahedron Lett. 1999, 40, 2435.
79. (a) Le, T. P. T.; Moad, G.; Rizzardo, E.; Thang, S. H. PCT Int. WO 98/ 01478.
80. (b) Chiefari, J.; Chong, Y. K.; Ercole, F.; Krstina, J.; Jeffery, J.; Le, T. P. T.; Mayadunne, R. T. A.; Meijs, G. F.; Moad, C. L.; Moad, G.; Rizzardo, E.; Thang, S. H. Macromolecules 1998, 31, 5559.
81. (a) Convertine, A. J.; Sumerlin, B. S.; Thomas, D. B.; Lowe, A. B.; McCormick, C. L. Macromolecules 2003, 36, 4679.
82. (b) McCormick, C. L.; Lowe, A. B. Acc. Chem. Res. 2004, 37, 312.