Organo-catalyzed ring opening polymerization of a 1,4-dioxane-2,5-dione deriving from glutamic acid

Biomacromolecules

Volumn 11, Issue 8, 2010, Pages 1921-1929

  Du Boullay, Olivier Thillaye ^a,b   Saffon, Nathalie ^a   Diehl, Jean Pierre ^c   Martin Vaca, Blanca ^a,b   Bourissou, Didier ^a,b  

^a UNIVERSITÉ PAUL SABATIER   (France)

^b CNRS   (France)

^c Université Paul Sabatier ^*  (France)

Author keywords

[No Author keywords available]

Indexed keywords

4-DIMETHYLAMINOPYRIDINE; CATALYZED RING OPENING POLYMERIZATION; DICHLOROMETHANE SOLUTIONS; EQUATORIAL POSITIONS; ESTER GROUPS; GLUTAMIC ACID; HYDROXYACIDS; LACTIDES; MALDI TOF MS; MATRIX-ASSISTED LASER DESORPTION IONIZATION; N-PENTANOL; NUMBER-AVERAGE; OH GROUP; PENDANT FUNCTIONAL GROUP; RANDOM DISTRIBUTION; RING OPENING; SIX-MEMBERED RINGS; SUBSTITUTION PATTERNS; TIME OF FLIGHT;

ACETYLATION; BROMINE COMPOUNDS; CARBOXYLIC ACIDS; DESORPTION; DICHLOROMETHANE; ESTERS; ETHERS; FUNCTIONAL GROUPS; FUNCTIONAL POLYMERS; MASS SPECTROMETRY; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC ACIDS; POLYDISPERSITY; POLYMERS; RESONANCE; SIZE EXCLUSION CHROMATOGRAPHY; THIOUREAS; UREA; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

RING OPENING POLYMERIZATION;

2 HYDROXYACID; 4 DIMETHYLAMINOPYRIDINE; [(BENZYLOXYCARBONYL)ETHYL] 1,4 DIOXANE 2,5 DIONE; ACETIC ACID DERIVATIVE; BROMINE DERIVATIVE; BROMOACETYL BROMIDE; CARBOXYLIC ACID DERIVATIVE; DIOXANE DERIVATIVE; ESTER DERIVATIVE; FUNCTIONAL GROUP; GLUTAMIC ACID DERIVATIVE; HYDROXYL GROUP; ORGANIC COMPOUND; PENTANOL; SPARTEINE; THIOUREA; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; GEL PERMEATION CHROMATOGRAPHY; HETERONUCLEAR MULTIPLE BOND CORRELATION; HYDROGENOLYSIS; MASS; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; X RAY DIFFRACTION;

CATALYSIS; CHROMATOGRAPHY, GEL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIOXANES; GLUTAMIC ACID; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; POLYMERS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; X-RAY DIFFRACTION;

EID: 77955575348     PISSN: 15257797     EISSN: 15264602     Source Type: Journal    
DOI: 10.1021/bm100433c     Document Type: Article

References (77)

1. For general reviews dealing with the applications of PLA, see
2. Jain, R. A. Biomaterials 2000, 21, 2475-2490
3. Drumright, R. E.; Gruber, P. R.; Henton, D. E. Adv. Mater. 2000, 12, 1841-1846
4. Albertsson, A.-C.; Varma, I. K. Biomacromolecules 2003, 4, 1466-1486
5. Auras, R.; Harte, B.; Selke, S. Macromol. Biosci. 2004, 4, 835-864
6. Mecking, S. Angew. Chem., Int. Ed. 2004, 43, 1078-1086
7. Gupta, A. P.; Kumar, V. Eur. Polym. J. 2007, 43, 4053-4074
8. For reviews dealing with the preparation of PLA, see
9. O'Keefe, B. J.; Hillmyer, M. A.; Tolman, W. B. J. Chem. Soc., Dalton Trans. 2001, 2215-2224
10. Wu, J.; Yu, T. L.; Chen, T. C.; Lin, C. C. Coord. Chem. Rev. 2006, 250, 602-626
11. Wheaton, C. A.; Hayes, P. G.; Ireland, B. J. Dalton Trans. 2009, 4832-4846
12. Dechy-Cabaret, O.; Martin-Vaca, B.; Bourissou, D. Chem. Rev. 2004, 104, 6147-6176
13. Dechy-Cabaret, O.; Martin-Vaca, B.; Bourissou, D. In Handbook of Ring-Opening Polymerization; Dubois, P.; Coulembier, O.; Raquez, J.-M., Eds.; Wiley-VCH: Weinheim, 2009; pp 255 - 286.
14. Bourissou, D.; Moebs-Sanchez, S.; Martin-Vaca, B. C. R. Chim. 2007, 10, 775-794
15. Kamber, N. E.; Jeong, W.; Waymouth, R. M.; Pratt, R. C.; Lohmeijer, B. G. G.; Hedrick, J. L. Chem. Rev. 2007, 107, 5813-5840
16. Kiesewetter, M. K.; Shin, E. J.; Hedrick, J. L.; Waymouth, R. M. Macromolecules 2010, 43, 2093-2107
17. For recent reviews, see refs 2e,2f and Baker, G. L.; Vogel, E. B.; Smith, M. R. Polym. Rev 2008, 48, 64-84
18. Pounder, R. J.; Dove, A. P. Polym. Chem. 2010, 1, 260-271
19. Yin, M.; Baker, G. L. Macromolecules 1999, 32, 7711-7718
20. Simmons, T. L.; Baker, G. L Biomacromolecules 2001, 2, 658-663
21. Liu, T.; Simmons, T. L.; Bohnsack, D. A.; Mackay, M. E.; Smith, M. R., III; Baker, G. L. Macromolecules 2007, 40, 6040-6047
22. Jing, F.; Smith, M. R., III; Baker, G. L. Macromolecules 2007, 40, 9304-9312
23. Marcincinova-Benabdillah, K.; Coudane, J.; Boustta, M.; Engel, R.; Vert, M. Macromolecules 1999, 32, 8774-8780
24. Marcincinova-Benabdillah, K.; Boustta, M.; Coudane, J.; Vert, M. Biomacromolecules 2001, 2, 1279-1284
25. Saulnier, B.; Coudane, J.; Garreau, H.; Vert, M. Polymer 2006, 47, 1921-1929
26. For related 1,4-dioxane-2,5-diones deriving from l-ascorbic and d-isoascorbic acids, see
27. Bueno, M.; Molina, I.; Galbis, J. A. Carbohydr. Res. 2009, 344, 2100-2104
28. Yang, J. Y.; Yu, J.; Pan, H. Z.; Gu, Z. W.; Cao, W. X.; Feng, X. D. Chin. J. Polym. Sci. 2001, 19, 509-516
29. Leemhuis, M.; van Steenis, J. H.; van Uxem, M. J.; van Nostrum, C. F.; Hennink, W. E. Eur. J. Org. Chem. 2003, 3344-3349
30. Leemhuis, M.; van Nostrum, C. F.; Kruijtzer, J. A. W.; Zhong, Z. Y.; ten Breteler, M. R.; Dijkstra, P. J.; Feijen, J.; Hennink, W. E. Macromolecules 2006, 39, 3500-3508
31. Gerhardt, W. W.; Noga, D. E.; Hardcastle, K. I.; Garcia, A. J.; Collard, D. M.; Weck, M. Biomacromolecules 2006, 7, 1735-1742
32. Loontjens, C. A. M.; Vermonden, T.; Leemhuis, M.; van Steenbergen, M. J.; van Nostrum, C. F.; Hennink, W. E. Macromolecules 2007, 40, 7208-7216
33. Kimura, Y.; Shirotani, K.; Yamane, H.; Kitao, T. Macromolecules 1988, 21, 3338-3340
34. Kimura, Y.; Shirotani, K.; Yamane, H.; Kitao, T. Polymer 1993, 34, 1741-1748
35. Yamaoka, T.; Hotta, Y.; Kobayashi, K.; Kimura, Y. Int. J. Biol. Macromol. 1999, 25, 265-271
36. For the related symmetric 1,4-dioxane-2,5-dione featuring two pendant carboxybenzylmethyl groups, see
37. Ouchi, T.; Fujino, A. Makromol. Chem. 1989, 190, 1523-1530
38. 2: Tetsuya, Y.; Takashi, K. WO2005121904, 2005.
39. For 1,4-dioxane-2,5-diones featuring allyl, propargyl, and oligo(ethylene oxide) pendant groups, see
40. Jiang, X.; Vogel, E. B.; Smith, M. R., III; Baker, G. L. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 5227-5236
41. Leemhuis, M.; Akeroyd, N.; Kruijtzer, J. A. W.; van Nostrum, C. F.; Hennink, W. E. Eur. Polym. J. 2008, 44, 308-317
42. Jiang, X.; Vogel, E. B.; Smith, M. R., III; Baker, G. L. Macromolecules 2008, 41, 1937-1944
43. Jiang, X.; Smith, M. R., III; Baker, G. L. Macromolecules 2008, 41, 318-324
44. Leemhuis, M.; Kruijtzer, J. A. W.; van Nostrum, C. F.; Hennink, W. E. Biomacromolecules 2007, 8, 2943-2949
45. Noga, D. E.; Petrie, T. A.; Kumar, A.; Weck, M.; Garcia, A. J.; Collard, D. M. Biomacromolecules 2008, 9, 2056-2062
46. Ghassemi, A. H.; van Steenbergen, M. J.; Talsma, H.; van Nostrum, C. F.; Jiskoot, W.; Hennink, W. E. J. Controlled Release 2009, 138, 57-63
47. Li, Y.; Li, Q.; Li, F.; Zhang, H.; Jia, L.; Yu, J.; Fang, Q.; Cao, A. Biomacromolecules 2006, 7, 224-231
48. Coulembier, O.; Kiesewetter, M. K.; Mason, A.; Dubois, P.; Hedrick, J. L.; Waymouth, R. M. Angew. Chem., Int. Ed. 2007, 46, 4719-4721
49. Fukushima, K.; Pratt, R. C.; Nederberg, F.; Tan, J. P. K.; Yang, Y. Y.; Waymouth, R. M.; Hedrick, J. L. Biomacromolecules 2008, 9, 3051-3056
50. Pounder, R. J.; Stanford, M. J.; Brooks, P.; Richards, S. P.; Dove, A. P. Chem. Commun. 2008, 5158-5160
51. Dove, A. P. Chem. Commun. 2008, 6446-6470
52. Kim, S. H;; Tan, J. P. K.; Nederberg, F.; Fukushima, K.; Yang, Y. Y.; Waymouth, R. M.; Hedrick, J. L. Macromolecules 2009, 42, 25-29
53. Misaka, H.; Kakuchi, R.; Zhang, C.; Sakai, R.; Satoh, T.; Kakuchi, T. Macromolecules 2009, 42, 5091-5096
54. Nederberg, F.; Appel, E.; Tan, J. P. K.; Kim, S. H.; Fukushima, K.; Sly, J.; Miller, R. D.; Waymouth, R. M.; Yang, Y. Y.; Hedrick, J. L. Biomacromolecules 2009, 10, 1460-1468
55. Thillaye du Boullay, O.; Marchal, E.; Martin-Vaca, B.; Cossio, F. P.; Bourissou, D. J. Am. Chem. Soc. 2006, 128, 16442-16443
56. Bonduelle, C.; Martín-Vaca, B.; Cossío, F. P.; Bourissou, D. Chem.-Eur. J. 2008, 14, 5304-5312
57. Thillaye du Boullay, O.; Bonduelle, C.; Martin-Vaca, B.; Bourissou, D. Chem. Commun. 2008, 1786-1788
58. Jing, F.; Hillmyer, M. A. J. Am. Chem. Soc. 2008, 130, 13826-13827
59. Pratt, R. C.; Lohmeijer, B. G. G.; Long, D. A.; Pontus Lundberg, P. N.; Dove, A. P.; Li, H.; Wade, C. G.; Waymouth, R. M.; Hedrick, J. L. Macromolecules 2006, 39, 7863-7871
60. Vitrant, A.-M.; Ferruccio, L. EP1439166 (A1), 2004.
61. Deechongkit, S.; You, S.-L.; W; Kelly, J Org. Lett. 2004, 6, 497-500
62. SADABS, version 2.10, Program for data correction, Bruker-AXS, 2003.
63. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467
64. Sheldrick, G. M. SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen, Germany, 1997.
65. Van Hummel, G. J.; Harkema, S.; Kohn, F. E.; Feijen, J. Acta Crystallogr. 1982, B38, 1679-1681
66. Lynch, V. W.; Pojman, J.; Whitesell, J. K.; Davis, B. E. Acta Crystallogr. 1990, C46, 1125-1127
67. Bolte, M.; Beck, H.; Nieger, M.; Egert, E. Acta Crystallogr. 1994, C50, 1717-1721
68. Chisholm, M. H.; Eilerts, N. W.; Huffman, J. C.; Iyer, S. S.; Pacold, M.; Phomphrai, K. J. Am. Chem. Soc. 2000, 122, 11845-11854
69. Kooijman, H.; Leemhuis, M.; van Nostrum, C. F.; Hennink, W. E.; Spek, A. L Acta Crystallogr. 2005, E61, o898-900 o901-903, and o3480-3481
70. Nederberg, F.; Connor, E. F.; Möller, M.; Glauser, T.; Hedrick, J. L. Angew. Chem., Int. Ed. 2001, 40, 2712-2715
71. Dove, A. P.; Pratt, R. C.; Lohmeijer, B. G. G.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2005, 127, 13798-13799
72. Zhu, R.-X.; Wang, R.-X.; Zhang, D.-J.; Liu, C.-B. Aust. J. Chem. 2009, 62, 157-164
73. Baran, J.; Duda, A.; Penczek, S.; Kowalski, A.; Szymanski, R. Macromol. Rapid Commun. 1997, 18, 325-333
74. Kowalski, A.; Libiszowski, J.; Duda, A.; Penczek, S. Macromolecules 2000, 33, 1964-1971
75. Thillaye du Boullay, O.; Martin-Vaca, B.; Bourissou, D.; Diehl, J.-P. FR09/01051, 2009.
76. For the DBU-catalyzed ROP of lactide, see
77. Lohmeijer, B. G. G.; Pratt, R. C.; Leibfarth, F.; Logan, J. W.; Long, D. A.; Dove, A. P.; Nederberg, F.; Choi, J.; Wade, C.; Waymouth, R. M.; Hedrick, J. L. Macromolecules 2006, 39, 8574-8583