Ring-opening polymerization of lactides catalyzed by magnesium complexes coordinated with NNO-tridentate pyrazolonate ligands

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 51, Issue 3, 2013, Pages 696-707

  Chuang, Hui Ju ^a   Chen, Hsiao Li ^a   Ye, Jian Li ^a   Chen, Zn Yun ^a   Huang, Pei Ling ^a   Liao, Tzu Ting ^a   Tsai, Tsung En ^a   Lin, Chu Chieh ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

catalysts; kinetics (polym.); polyesters; ring opening polymerization

Indexed keywords

ANCILLARY LIGANDS; DINUCLEAR; ELECTRON-DONATING SUBSTITUENTS; ELECTRONIC EFFECTS; KINETIC STUDY; KINETICS(POLYM.); L-LACTIDE; LACTIDES; MAGNESIUM COMPLEXES; METAL CENTERS; OXYGEN ATOM; PHENYL RINGS; POLY LACTIDE; POLYDISPERSITY INDICES; POLYMER CHAINS; POLYMERIZATION RATES; RAC-LACTIDE; X-RAY CRYSTAL STRUCTURAL;

BIOGRAPHIES; CATALYSTS; CRYSTAL ATOMIC STRUCTURE; MAGNESIUM; METAL COMPLEXES; POLYESTERS; RING OPENING POLYMERIZATION; SYNTHESIS (CHEMICAL);

LIGANDS;

EID: 84872867397     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.26426     Document Type: Article

References (87)

1. (a), B. Jeong, Y. H. Bae, D. S. Lee, S. W. Kim, Nature (London) 1997, 388, 860-862
2. (b), R. E. Drumright, P. R. Gruber, D. E. Henton, Adv. Mater. 2000, 12, 1841-1846
3. (c), R. A. Gross, B. Kalra, Science 2002, 297, 803-807
4. (d), Y. Y. Li, F. Cunin, J. R. Link, T. Gao, R. E. Betts, S. H. Reiver, V. Chin, S. N. Bhatia, M. J. Sailor, Science 2003, 299, 2045-2047
5. (e), R. Auras, B. Harte, S. Selke, Macromol. Biosci. 2004, 4, 835-864.
6. (a), B. J. O'Keefe, M. A. Hillmyer, W. B. Tolman, J. Chem. Soc., Dalton Trans, 2001, 2215-2224
7. (b), D. C. Odile, M. V. Blanca, B. Didier, Chem. Rev. 2004, 104, 6147-6176
8. (c), R. H. Platel, L. M. Hodgson, C. K. Williams, Polym. Rev. 2008, 48, 11-63
9. (d), S. Dutta, W.-C. Hung, B.-H. Huang, C.-C. Lin, Adv. Polym. Sci. 2012, 245, 219-284.
10. (a), C. K. Williams, L. E. Breyfogle, S. K. Choi, W. Nam, V. G. Young, Jr., M. A. Hillmyer, W. B. Tolman, J. Am. Chem. Soc. 2003, 125, 11350-11359
11. (b), L. E. Breyfogle, C. K. Williams, V. G. Young, Jr., M. A. Hillmyer, W. B. Tolman, Dalton Trans. 2006, 928-936
12. (c), C. A. Wheaton, P. G. Hayes, B. J. Ireland, Dalton Trans. 2009, 4832-4846
13. (d), G. Labourdette, D. J. Lee, O. Patrick, M. B. Ezhova, P. Mehrkhodavandi, Organometallics 2009, 28, 1309-1319
14. (e), L. Wang, H. Ma, Macromolecules 2010, 43, 6535-6537
15. (f), D. J. Darensbourg, O. Karroonnirun, Inorg. Chem. 2010, 49, 2360-2371
16. (g), L. Wang, H. Ma, Dalton Trans. 2010, 39, 7897-7910.
17. (a), M.-L. Shieuh, S.-L. Lai, C.-C. Lin, Polymer 2005, 46, 9784-9792
18. (b), H.-Y. Chen, H.-Y. Tang, C.-C. Lin, Macromolecules 2006, 39, 3745-3752
19. (c), J. Wu, X. Pan, N. Tang, C.-C. Lin, Eur. Polym. J. 2007, 43, 5040-5046
20. (d), G. Labourdette, D. J. Lee, B. O. Patrick, M. B. Ezhova, P. Mehrkhodavandi, Organometallics 2009, 28, 1309-1319
21. (e), W.-C. Hung, C.-C. Lin, Inorg. Chem. 2009, 48, 728-734
22. (f), X. Pang, H. H. Du, X. Chen, X. M. Wang, X. Jing, Chem. Eur. J. 2008, 14, 3126-3136
23. (g), D. J. Darensbourg, O. Karroonnirun, Organometallics 2010, 29, 5627-5634
24. (h), D. J. Darensbourg, O. Karroonnirun, Inorg. Chem. 2010, 49, 2360-2371.
25. (a), R.-C. Yu, C.-H. Hung, J.-H. Huang, H.-Y. Lee, J.-T. Chen, Inorg. Chem. 2002, 41, 6450-6455
26. (b), B.-L. Lin, K. X. Bhattacharyya, J. A. Labinger, J. E. Bercaw, Organometallics 2009, 28, 4400-4405
27. (c), W.-Y. Lee, H.-H. Hsieh, C.-C. Hsieh, H.-M. Lee, G.-H. Lee, J.-H. Huang, T.-C. Wu, S.-H. Chuang, J. Organomet. Chem. 2007, 692, 1131-113 7
28. (d), H.-Y. Tang, H.-Y. Chen, C.-C. Lin, Macromolecules 2007, 40, 8855-8860
29. (e), B. Sedai, M. J. Heeg, C. H. Winter, Organometallics 2009, 28, 1032-1038
30. (f), F. Drouin, P. O. Oguadinma, T. J. J. Whitehorne, R. E. Prud'homme, F. Schaper, Organometallics 2010, 29, 2139-2147.
31. (a), F. Marchetti, C. Pettinari, R. Pettinari, Coord. Chem. Rev. 2005, 249, 2909-2945
32. (b), B. A. Uzoukwd, K. Gloe, P. U. Adiukwu, Synth. React. Inorg. Met.-Org. Chem. 2000, 20, 433-443.
33. (a), M. H. Chisholm, J. C. Gallucci, K. Phomphrai, Chem. Commun. 2003, 48-49
34. (b), M. H. Chisholm, J. C. Gallucci, K. Phomphrai, Inorg. Chem. 2004, 43, 6717-6725
35. (c), S. Milione, F. Grisi, R. Centore, A. Tuzi, Organometallics 2006, 25, 266-274
36. (d), C. Zhang, Z.-X. Wang, J. Organomet. Chem. 2008, 693, 3151-3158
37. (e), Z. Zheng, G. Zhao, R. Fablet, M. Bouyahyi, C. M. Thomas, T. Roisnel, O. Casagrande, Jr., J.-F. Carpentier, New J. Chem. 2008, 32, 2279-2291
38. (f), K.-F. Peng, C.-T. Chen, Dalton Trans. 2009, 9800-9806.
39. (a), S. Li, Macromol. Biosci. 2003, 3, 657-661
40. (b), H. Urayama, T. Kanamori, K. Fukushima, Y. Kimura, Polymer 2003, 44, 5635-5641
41. (c), K. Paakinaho, V. Ellä, S. Syrjälä, M. Kellomäki, Polym. Degrad. Stab. 2009, 94, 438-442
42. (d), H. Tsuji, S. Kamo, F. Horii, Polymer 2010, 51, 2215-2220
43. (e), J. Sun, H. Yu, X. Zhuang, X. Chen, X. Jing, J. Phys. Chem. B 2011, 115, 2864-2869.
44. (a), M. Wisniewski, A. L. Borgne, N. Spassky, Macromol. Chem. Phys. 1997, 198, 1227-1238
45. (b), C. P. Radano, G. L. Baker, M. R. Smith, III, J. Am. Chem. Soc. 2000, 122, 1552-1553
46. (c), T. M. Ovitt, G. W. Coates, J. Polym. Sci. Part A: Polym. Chem. 2000, 38, 4686-4692.
47. (a), M. H. Chisholm, N. J. Patmore, Z. Zhou, Chem. Commun. 2005, 127, 127-129
48. (b), M. H. Chisholm, J. C. Gallucci, K. T. Quisenberry, Z. Zhou, Inorg. Chem. 2008, 47, 2613-2624
49. (c), Z. Zhong, P. J. Dijkstra, J. Feijen, Angew. Chem. Int. Ed. 2002, 41, 4510-4513
50. (d), Z. Y. Zhong, P. J. Dijkstra, J. Feijen, J. Am. Chem. Soc. 2003, 125, 11291-11298
51. (e), N. Nomura, R. Ishii, M. Akakura, K. Aoi, J. Am. Chem. Soc. 2002, 124, 5938-5939
52. (f), N. Nomura, R. Ishii, Y. Yamamoto, T. Kondo, Chem. Eur. J. 2007, 13, 4433-4451
53. (g), E. L. Marshall, V. C. Gibson, R. I. Pugh, A. J. P. White, Proc. Natl. Acad. Sci. USA 2006, 103, 15343-15348
54. (h), H.-L. Chen, S. Dutta, P.-Y. Huang, C.-C. Lin, Organometallics 2012, 31, 2016-2025.
55. P. Hormnirun, E. L. Marshall, V. C. Gibson, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 2004, 126, 2688-2689.
56. (a), M. Cheng, A. B. Attygalle, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 1999, 121, 11583-11584
57. (b), B. M. Chamberlain, M. Cheng, D. R. Moore, T. M. Ovitt, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 2001, 123, 3229-3238
58. (c), M. H. Chisholm, J. Gallucci, K. Phomphrai, Inorg. Chem. 2002, 41, 2785-2794
59. (d), M. H. Chisholm, J. C. Gallucci, K. Phomphrai, Inorg. Chem. 2005, 44, 8004-8010.
60. (a), X. Liu, X. Shang, T. Tang, N. Hu, F. Pei, D. Cui, X. Chen, X. Jing, Organometallics 2007, 26, 2747-2757
61. (b), A. Amgoune, C. M. Thomas, J.-F. Carpentier, Macromol. Rapid Commun. 2007, 28, 693-697
62. (c), M. Bouyahyi, N. Ajellal, E. Kirillov, C. M. Thomas, J.-F. Carpentier, Chem. Eur. J. 2011, 17, 1872-1883
63. (d), W. Zhao, D. Cui, X. Liu, X. Chen, Macromolecules 2010, 43, 6678-6684
64. (e), K. Nie, X. Gu, Y. Yao, Y. Zhang, Q. Shen, Dalton Trans. 2010, 39, 6832-6840.
65. (a), H. Y. Ma, T. P. Spaniol, J. Okuda, Angew. Chem. Int. Ed. 2006, 45, 7818-7821
66. (b), H. Ma, T. P. Spaniol, J. Okuda, Inorg. Chem. 2008, 47, 3328-3329.
67. M. H. Chisholm, J. Gallucci, K. Phomphrai, Chem. Commun. 2003, 48-49.
68. (a), A. Pietrangelo, M. A. Hillmyer, W. B. Tolman, Chem. Commun. 2009, 2736-2737
69. (b), A. Pietrangelo, S. C. Knight, A. K. Gupta, L. J. Yao, M. A. Hillmyer, W. B. Tolman, J. Am. Chem. Soc. 2010, 132, 11649-11657.
70. (a), Y. Huang, W.-C. Hung, M.-Y. Liao, T.-E. Tsai, Y.-L. Peng, C.-C. Lin, J. Polym. Sci. Part A: Polym. Chem. 2009, 47, 2318-2329
71. (b), H.-J. Chuang, Y.-C. Su, B.-T. Ko, C.-C. Lin, Inorg. Chem. Commun. 2012, 18, 38-42.
72. (a), B. S. Jensen, Acta. Chem. Scand. 1959, 13, 1668-1670
73. (b), W. Holzer, R. M. Claramunt, M. D. Perez-Torralba, D. Guggi, T. H. Brehmer, J. Org. Chem. 2003, 68, 7943-7950.
74. (a), G. Wider, V. Dötsch, K. Wüthrich, J. Magn. Reson. 1994, 108A, 255-258
75. (b), M. Valentini, P. S. Pregosin, H. Rüegger, Organometallics 2000, 19, 2551-2555
76. (c), J. P. Stamps, B. Ottink, J. M. Visser, J. P. M. Duynhoven, R. Hulst, J. Magn. Reson. 2001, 151, 28-31
77. (d), R. Crimmin, M. S. Hill, J. R. Lachs, M. F. Mahon, P. A. Procopiou, Inorg. Chem. 2009, 48, 4445-4453.
78. G. M. Sheldrick, SHELXTL-Plus, NT Crystallographic System, release 5.1; Bruker Analytical X-ray Systems: Madison, WI, 1998.
79. A. W. Addison, T. N. Rao, J. Reedijk, J. V. Rijn, G. C. Verschoor, J. Chem. Soc., Dalton Trans. 1984, 1349-1356.
80. (a), J. Baran, A. Duda, A. Kowalski, R. Szymanski, S. Penczek, Macromol. Rapid Commun. 1997, 18, 325-333
81. (b), T. Biela, A. Duda, S. Penczek, Macromol. Symp. 2002, 183, 1-10
82. (c), M. Save, M. Schappacher, A. Soum, Macromol. Chem. Phys. 2002, 203, 889-899.
83. (a), J. E. Kasperczyk, Macromolecules 1995, 28, 3937-3939
84. (b), J. Coudane, C. Ustariz-Peyret, G. Schwach, M. Vert, J. Polym. Sci. Part A: Polym. Chem. 1997, 35, 1651-1658.
85. H.-J. Chuang, H.-L. Chen, T.-E. Tsai, P.-L. Huang, T.-T. Liao, C.-C. Lin, unpublished work.
86. (a), A. P. Dove, V. C. Gibson, E. L. Marshall, H. S. Rzepa, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 2006, 128, 9834-9843
87. (b), M. H. Chisholm, N. W. Eilerts, J. C. Huffman, S. S. Iyer, M. Pacold, K. Phomphrai, J. Am. Chem. Soc. 2000, 122, 11845-11854.