Efficient zinc initiators supported by NNO-tridentate ketiminate ligands for cyclic esters polymerization

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 51, Issue 5, 2013, Pages 1185-1196

  Chuang, Hui Ju ^a   Chen, Hsiao Li ^a   Huang, Bor Hunn ^a   Tsai, Tsung En ^a   Huang, Pei Ling ^a   Liao, Tzu Ting ^a   Lin, Chu Chieh ^a  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

Author keywords

butyrolactone; caprolactone; decalactone; catalysts; L lactide; polyethers; ring opening polymerization (ROP); zinc

Indexed keywords

BUTYROLACTONES; CAPROLACTONE; CYCLIC ESTERS; DINUCLEAR; FIRST ORDER REACTIONS; KINETIC STUDY; L-LACTIDE; LACTIDES; METAL CENTERS; OXYGEN ATOM; PLLA; X-RAY CRYSTAL STRUCTURAL;

CATALYSTS; CRYSTAL ATOMIC STRUCTURE; ETHERS; LIGANDS; METAL COMPLEXES; POLYETHERS; SYNTHESIS (CHEMICAL); ZINC;

POLYMERIZATION;

EID: 84872894094     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.26486     Document Type: Article

References (94)

1. (a), B. Jeong, Y. H. Bae, D. S. Lee, S. W. Kim, Nature (Lond.) 1997, 388, 860-862
2. (b), R. A. Gross, B. Kalra, Science, 2002, 297, 803-807
3. (c), Y. Y. Li, F. Cunin, J. R. Link, T. Gao, R. E. Betts, S. Reiver, H. V. Chin, S. N. Bhatia, M. J. Sailor, Science, 2003, 299, 2045-2047
4. (d), R. E. Drumright, P. R. Gruber, D. E. Henton, Adv. Mater. 2000, 12, 1841-1846.
5. (a), B. J. O'Keefe, H. A. Hillmyer, W. B. Tolman, J. Chem. Soc. Dalton Trans. 2001, 30, 2215-2224
6. (b), O. Dechy-Cabaret, B. Martin-Vaca, D. Bourissou, Chem. Rev. 2004, 104, 6147-6176
7. (c), J. Wu, T. L. Yu, C. T. Chen, C. C. Lin, Coord. Chem. Rev. 2006, 250, 602-626
8. (d), R. H. Platel, L. M. Hodgson, C. K. Williams, Polym. Rev. 2008, 48, 11-63
9. (e), C. M. Thomas, Chem. Soc. Rev. 2010, 39, 165-173
10. (f), M. H. Chisholm, Pure Appl. Chem. 2010, 82, 1647-1662.
11. (a), 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
12. (b), M. H. Chisholm, J. Gallucci, K. Phomphrai, Inorg. Chem. 2002, 41, 2785-2794
13. (c), C. K. Williams, Chem. Soc. Rev. 2007, 36, 1573-1580
14. (d), C. A. Wheaton, P. G. Hayes, B. J. Ireland, Dalton Trans. 2009, 38, 4832-4846.
15. (a) Example for Aluminum complexes:, C. P. Radano, G. L. Bake, M. R. Smith, J. Am. Chem. Soc. 2000, 122, 1552-1553
16. (b), Y.-C. Liu, B.-T. Ko, C.-C. Lin, Macromolecules 2001, 34, 6196-6201
17. (c), T. M. Ovitt, G. W. Coates, J. Am. Chem. Soc. 2002, 124, 1316-1326
18. (d), Z. Zhong, P. J. Dijkstra, J. Feijen, J. Am. Chem. Soc. 2003, 125, 11291-11298
19. (e), L. M. Alcazar-Roman, B. J. O'Keefe, M. A. Hillmyer, W. B. Tolman, Dalton Trans. 2003, 33, 3082-3087
20. (f), K. Majerska, A. Duda, J. Am. Chem. Soc. 2004, 126, 1026-1027
21. (g), M. H. Chisholm, N. J. Patmore, Z. Zhou, Chem. Commun. 2005, 41, 127-129
22. (h), X. Pang, H.-Z. Du, X.-S. Chen, X.-H. Wang, X.-B. Jing, Chem. Eur. J. 2008, 14, 3126-3136
23. (i), M. Bouyahyi, T. Roisnel, J. F. Carpentier, Organometallics 2010, 29, 491-500
24. (j), D. J. Darensbourg, O. Karroonnirun, Organometallics, 2010, 29, 5627-5634
25. (k), J. Koller, R. G. Bergman, Organometallics 2011, 30, 3217-3224
26. (l), C.-Y. Li, C.-Y. Tsai, C.-H. Lin, B.-T. Ko, Dalton Trans. 2011, 40, 1880-1887.
27. (a) Example for Tin complexes:, H. R. Kricheldorf, M. V. Sumbbl, I. K. Saunders, Macromolecules 1991, 24, 1944-1949
28. (b), K. B. Aubrecht, M. A. Hillmyer, W. B. Tolman, Macromolecules 2002, 35, 644-650
29. (c), B. Amsden, S. Wang, U. Wyss, Biomacromolecules 2004, 5, 1399-1404
30. (d), N. Nimitsiriwat, E. L. Marshall, V. C. Gibson, M. R. J. Elsegood, S. H. Dale, J. Am. Chem. Soc. 2004, 126, 13598-13599
31. (e), 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
32. (f), W. A. Ma, Z. X. Wang, Dalton Trans. 2011, 40, 1778-1786
33. (g), A. Ishii, K. Asajima, T. Toda, N. Nakata, Organometallics 2011, 30, 2947-2956
34. (h), J.-C. Buffet, J. Okuda, Chem. Commun. 2011, 47, 4796-4798.
35. (a) Example for Lanthanide complexes:, W. M. Stevels, M. T. Ankone, P. J. Dijkstra, J. Feijen, Macromolecules 1996, 29, 3332-3333
36. (b), V. Simic, N. Spassky, I. G. Hubert-Pfalzgraf, Macromolecules 1997, 30, 7338-7340
37. (c), X. Deng, M. Yuan, C. Xiong, X. J. Li, Appl. Polym. Sci. 1999, 1401-1408
38. (d), S. A. Schuetz, C. M. Silvernail, C. D. Incarvito, A. L. Rheingold, J. L. Clark, V. W. Day, J. A. Belot, Inorg. Chem. 2004, 43, 6203-6214
39. (e), H. Ma, T. P. Spaniol, J. Okuda, Inorg. Chem. 2008, 47, 3328-3339
40. (f), P. I. Binda, E. E. Delbridge, H. B. Abrahamson, B. W. Skelton, Dalton Trans. 2009, 38, 2777-2787
41. (g), M. Q. Xue, R. Jiao, Y. Zhang, Y. M. Yao, Q. Shen, Eur. J. Inorg. Chem. 2009, 2009, 4110-4118
42. (h), R. H. Platel, A. J. P. White, C. K. Williams, Inorg. Chem. 2011, 50, 7718-7728
43. (i), T.-P.-A. Cao, A. Buchard, X. F. L. Goff, A. Auffrant, C. K. Williams, Inorg. Chem. 2012, 51, 2157-2169.
44. (a) Example for Iron complexes:, B. J. O'Keefe, L. E. Breyfogle, M. A. Hillmyer, W. B. Tolman, J. Am. Chem. Soc. 2002, 124, 4384-4393
45. (b), P. Dobrzynski, J. Kasperczyk, M. Janeczek, M. Bero, Polymer 2002, 43, 2595-2601
46. (c), X. Wang, K. Liao, D. Quan, Q. Wu, Macromolecules 2005, 38, 4611-4617
47. (d), V. C. Gibson, E. L. Marshall, D. N. Llobet, A. J. P. White, D. J. Williams, J. Chem. Soc., Dalton Trans. 2002, 4321-4322
48. (e), M.-Z. Chen, H.-M. Sun, W.-F. Li, Z.-G. Wang, Q. Shen, Y. Zhang, J. Organom. Chem. 2006, 691, 2489-2494
49. (f), J. Chen, J. L. Gorczynski, C. L. Fraser, Macromol. Chem. Phys. 2010, 211, 1272-1279.
50. (a) Example for Magnesium complexes:, M. H. Chisholm, N. W. Eilerts, J. C. Huffman, S. S. Iyer, M. Pacold, K. Phomphrai, J. Am. Chem. Soc. 2000, 122, 11845-11854
51. (b), E. L. Marshall, V. C. Gibson, H. S. Rzepa, J. Am. Chem. Soc. 2005, 127, 6048-6051
52. (c), L. E. Breyfogle, C. K. Williams, V. G. Young, Jr., M. A. Hillmyer, W. B. Tolman, Dalton Trans. 2006, 35, 928-936
53. (d), L. Wang, H. Ma, Macromolecules 2010, 43, 6535-6537
54. (e), F. Drouin, T. J. J. Whitehorne, F. Schaper, Dalton Trans. 2011, 40, 1396-1400
55. (f), A. Grala, J. Ejfler, L. B. Jerzykiewicz, P. Sobota, Dalton Trans. 2011, 40, 4042-4044
56. (g), C.-Y. Sung, C.-Y. Li, J.-K. Su, T.-Y. Chen, C.-H. Lin, B.-T. Ko, Dalton Trans. 2012, 41, 953-961
57. (h), V. Poirier, T. Roisnel, J.-F. Carpentier, Y. Sarazin, Dalton Trans. 2011, 40, 523-534.
58. (a) Example for Zinc complexes:, M. Cheng, A. B. Attygalle, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 1999, 121, 11583-11584
59. (b), C. M. Silvernail, L. J. Yao, L. M. R. Hill, M. A. Hillmyer, W. B. Tolman, Inorg. Chem. 2007, 46, 6565-6574
60. (c), D. J. Darensbourg, O. Karroonnirun, Inorg. Chem. 2010, 49, 2360-2371
61. (d), M.-T. Chen, C.-T. Chen, Dalton Trans. 2011, 40, 12886-12894
62. (e), R. M. Haak, A. Decortes, E. C. Escudero-Adán, M. Martínez Belmonte, E. Martin, J. A. Benet-Buchholz, W. Kleij, Inorg. Chem. 2011, 50, 7934-7936.
63. (a), R.-C. Yu, C.-H. Hung, J.-H. Huang, H.-Y. Lee, J.-T. Chen, Inorg. Chem. 2002, 41, 6450-6455
64. (b), J. Kido, Y. Okamoto, Chem. Rev. 2002, 102, 2357-2368
65. (c), F. Marchetti, C. C. Pettinari, R. Pettinari, Coord. Chem. Rev. 2005, 249, 2909-2945
66. (d), 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, 1131-1137
67. (e), B.-L. Lin, K. X. Bhattacharyya, J. A. Labinger, J. E. Bercaw, Organometallics 2009, 28, 4400-4405.
68. (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
69. (b), H.-Y. Tang, H.-Y. Chen, C.-C. Lin, Macromolecules 2007, 40, 8855-8860
70. (c), W.-C. Hung, Y. Huang, C.-C. Lin, J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 6466-6476
71. (d), J. Wu, X. Pan, N. Tang, C.-C. Lin, Eur. Polym. J. 2007, 43, 5040-5046
72. (e), A. F. Douglas, B. O. Patrick, P. Mehrkhodavandi, Angew. Chem., Int. Ed. Engl. 2008, 47, 2290-2293
73. (f), G. Labourdette, D. J. Lee, B. O. Patrick, M. B. Ezhova, P. Mehrkhodavandi, Organometallics 2009, 28, 1309-1319
74. (g), W.-C. Hung, C.-C. Lin, Inorg. Chem. 2009, 48, 728-734
75. (h), L. Wang, H. Ma, Dalton Trans. 2010, 39, 7897-7910
76. (i), C.-Y. Sung, C.-Y. Li, J.-K. Su, T.-Y. Chen, C.-H. Lin, B.-T. Ko, Dalton Trans. 2012, 41, 953-961
77. (j), C. Xu, I. Yu, P. Mehrkhodavandi, Chem. Commun. 2012, 48, 6806-6808.
78. (a), Huang, Y.,;, Hung, W.-C.,;, Liao, M.-Y.,;, Tsai, T.-E.,;, Peng, Y.-L.,;, Lin, C.-C., J. Polym. Sci. Part A: Polym. Chem., 2009, 47, 2318-2329
79. (b), Chuang, H.-J.,;, Su, Y.-C.,;, Ko, B.-T.,;, Lin, C.-C., Inorg. Chem. Commun., 2012, 18, 38-42.
80. (a), B. S. Jensen, Acta Chem. Scand. 1959, 13, 1668-1670
81. (b), W. Holzer, R. M. Claramunt, M. Perez-Torralba, D. Guggi, T. H. Brehmer, J. Org. Chem. 2003, 68, 7943-7950.
82. G. M. Sheldrick, SHELXTL-Plus, NT Crystallographic System, Release 5.1; Bruker Analytical X-ray Systems: Madison, WI, 1998.
83. (a), H.-Y. Chen, B.-H. Huang, C.-C. Lin, Macromolecules 2005, 38, 5400-5405
84. (b), F. Drouin, P. O. Oguadinma, T. J. J. Whitehorne, R. E. Prud'homme, F. Schaper, Organometallics 2010, 29, 2139-2147.
85. M. Cheng, D. R. Moore, J. J. Reckzek, B. M. Chamberlain, E. B. Lobkovsky, G. W. Coates, J. Am. Chem. Soc. 2001, 123, 8738-8749.
86. H.-Y. Chen, Y.-L. Peng, T.-H. Huang, A. K. Sutar, S. A. Miller, C.-C. Lin, J. Mol. Catal. A 2011, 339, 61-71.
87. (a), M. Frezza, S. S. Hindo, D. Tomco, M. Q. Allard, C. Cui, M. J. Heeg, D. Chen, Q. P. Dou, C. N. Verani, Inorg. Chem. 2009, 48, 5928-5973
88. (b), M. Wałȩsa-Chorab, H. B. Szcześniak, V. Patroniak, M. Kubicki, Z. Hnatejko, J. Harrowfield, A. R. Stefankiewicz, Polyhedron 2010, 29, 178-187.
89. A. W. Addison, T. N. Rao, J. Reedijk, J. V. Rijn, G. C. Verschoor, J. Chem. Soc., Dalton Trans. 1984, 14, 1349-1355.
90. n of polylactide. (a), J. Baran, A. Duda, A. Kowalski, R. Szymanski, S. Penczek, Macromol. Rapid Commun. 1997, 18, 325-333
91. (b), T. Biela, A. Duda, S. Penczek, Macromol. Symp. 2002, 183, 1-10
92. (c), M. Save, M. Schappacher, A. Soum, Macromol. Chem. Phys. 2002, 203, 889-899.
93. (a), J. C. Wu, B. H. Huang, M. L. Hsueh, Polymer 2005, 46, 9784-9792
94. (b), H.-Y. Chen, H.-Y. Tang, C.-C. Lin, Macromolecules 2006, 39, 3745-3752.