High-speed living polymerization of polar vinyl monomers by self-healing silylium catalysts

Chemistry - A European Journal

Volumn 16, Issue 34, 2010, Pages 10462-10473

  Zhang, Yuetao ^a   Lay, Frank ^b   García García, Pilar ^b   List, Benjamin ^b   Chen, Eugene Y X ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Anions; Br ; Nsted acids; Polar vinyl monomers; Polymerization; Silicon

Indexed keywords

ANIONS; C-C BOND FORMATION; CATALYST LOADINGS; CHAIN EXTENSION; DEGREE OF CONTROL; EFFECTS OF ACID; HIGH-SPEED; IN-SITU; INDUCTION PERIODS; KETENE ACETALS; LINEAR GROWTH; LIVING POLYMERIZATION SYSTEMS; METHYL METHACRYLATES; MONOMER CONVERSIONS; MONOMER STRUCTURES; N-BUTYL ACRYLATE; NARROW MOLECULAR WEIGHT DISTRIBUTIONS; NSTED ACIDS; NUMBER-AVERAGE; OXONIUM ACIDS; POLYMERIZATION SYSTEMS; QUANTITATIVE EFFICIENCY; RATE LIMITING; REACTION TEMPERATURE; SELF-HEALING; SELF-REPAIR; STRONG ACIDS; TERMINATION REACTIONS; TURNOVER FREQUENCY; VINYL MONOMERS;

ACIDS; ACRYLIC MONOMERS; BLOCK COPOLYMERS; CATALYSTS; CHAIN LENGTH; CHEMICAL ACTIVATION; ESTERS; FREE RADICAL POLYMERIZATION; MOLECULAR WEIGHT DISTRIBUTION; NEGATIVE IONS; POLYMERS; SILICON; SYNTHESIS (CHEMICAL); WELL DRILLING;

LIVING POLYMERIZATION;

EID: 77956447655     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000961     Document Type: Article

References (77)

1. E. Y.-X. Chen, Chem. Rev. 2009, 109, 5157-5214.
2. H. L. Hsieh, R. P. Quirk, Anionic Polymerization. Principles and Practical Applications, Marcel Dekker, New York, 1996.
3. A. Rodriguez-Delgado, E. Y.-X. Chen, J. Am. Chem. Soc. 2005, 127, 961-974.
4. Selected comprehensive reviews: a) D. Baskaran, Prog. Polym. Sci. 2003, 28, 521-5811;
5. b) P. Vlèek, L. Lochmann, Prog. Polym. Sci. 1999, 24, 793-973;
6. c) C. Zune, R. Jérôme, Prog. Polym. Sci. 1999, 24, 631-664;
7. d) K. Hatada, T. Kitayama, K. Ute, Prog. Polym. Sci. 1988, 13, 189-276;
8. e) M. Van Beylen, S. Bywater, G. Smets, M. Szwarc, D. J. Worsfold, Adv. Polym. Sci. 1988, 86, 87-143.
9. O. W. Webster, W. R. Hertler, D. Y. Sogah, W. B. Farnham, T. V. RajanBabu, J. Am. Chem. Soc. 1983, 105, 5706-5708.
10. O. W. Webster, Adv. Polym. Sci. 2004, 167, 1-34.
11. a) A. H. E. Müller, G. Litvinenko, D. Yan, Macromolecules 1996, 29, 2346-2353;
12. b) R. P. Quirk, J.-S. Kim, J. Phys. Org. Chem. 1995, 8, 242-248;
13. c) R. P. Quirk, G. P. Bidinger, Polym. Bull. 1989, 22, 63-70.
14. T. Mukaiyama, Angew. Chem. 2004, 116, 5708-5733;
15. Angew. Chem. Int. Ed. 2004, 43, 5590-5614.
16. D. Y. Sogah, W. R. Hertler, O. W. Webster, G. M. Cohen, Macromolecules 1987, 20, 1473-1488.
17. a) J. Raynaud, Y. Gnanou, D. Taton, Macromolecules 2009, 42, 5996-6005;
18. b) J. Raynaud, A. Ciolino, A. Baceiredo, M. Destarac, F. Bonnette, T. Kato, Y. Gnanou, D. Taton, Angew. Chem. 2008, 120, 5470-5473;
19. Angew. Chem. Int. Ed. 2008, 47, 5390-5393;
20. c) M. D. Schölten, J. L. Hedrick, R. M. Waymouth, Macromolecules 2008, 41, 7399-7404.
21. W. R. Hertler, D. Y. Sogah, O. W. Webster, B. M. Trost, Macromolecules 1984, 17, 1415-1417.
22. Y. Zhang, E. Y.-X. Chen, Macromolecules 2008, 41, 36-42.
23. J. B. Lambert, S. Zhang, C. L. Stern, J. C. Huffman, Science 1993, 260, 1917-1918.
24. Y. Zhang, E. Y.-X. Chen, Macromolecules 2008, 41, 6353-6360.
25. a) H. Yamamoto, Tetrahedron 2007, 63, 8377-8412;
26. b) M. B. Boxer, H. Yamamoto, J. Am. Chem. Soc. 2006, 128, 48-49;
27. c) K. Ishihara, Y. Hiraiwa, H. Yamamoto, Synlett 2001, 1851-1854.
28. T. Akiyama, Chem. Rev. 2007, 107, 5744-5758.
29. P. Jutzi, C. Müller, A. Stammler, H. Stammler, Organometallics 2000, 19, 1442-1444.
30. a) E. B. Tjaden, D. C. Swenson, R. F. Jordan, Organometallics 1995, 14, 371-386;
31. b) H. W. Turner, G.G. Hlatky, R. R. Eckman, U.S. Patent 5, 198, 401, 1993.
32. P. García-García, F. Lay, P. García-García, C. Rabalakos, B. List, Angew. Chem. 2009, 127, 4427-4430;
33. Angew. Chem. Int. Ed. 2009, 48, 4363-4366.
34. R. Kakuchi, K. Chiba, K. Fuchise, R. Sakai, T. Satoh, T. Kakuchi, Macromolecules 2009, 42, 8747-8750.
35. B. Mathieu, L. Ghosez, Tetrahedron Lett. 1997, 38, 5497-5500.
36. K. Ute, H. Ohnuma, T. Kitayama, Polym. J. 2000, 32, 1060-1062.
37. R. Zhuang, A. H. X. Müller, Macromolecules 1995, 28, 8035-8042;
38. R. Zhuang, A. H. X. Müller, Macromolecules 1995, 28, 8043-8050.
39. K. Ute, H. Ohnuma, I. Shimizu, T. Kitayama, Polym. J. 2006, 38, 999-1003.
40. E. Y.-X. Chen, T. J. Marks, Chem. Rev. 2000, 100, 1391-1434.
41. Y. Zhang, Y. Ning, L. Caporaso, L. Cavallo, E. Y.-X. Chen, J. Am. Chem. Soc. 2010, 132, 2695-2709.
42. I. Krossing, I. Raabe, Angew. Chem. 2004, 116, 2116-2142;
43. Angew. Chem. Int. Ed. 2004, 43, 2066-2090.
44. Selected examples: a) C. A. Reed, Acc. Chem. Res. 2010, 43, 121-128;
45. b) H.F.T. Klare, M. Oestreich, Dalton Trans. 2010, DOI: 10.1039/c003097;
46. d) G. M. Miyake, Y. Zhang, E. Y.-X. Chen, Macromolecules 2010, 43, 4902-4908;
47. e) H. F. T. Klare, K. Bergander, M. Oestreich, Angew. Chem. 2009, 121, 9241;
48. Angew. Chem. Int. Ed. 2009, 48, 9077-9079;
49. e) C. Douvris, O. V. Ozerov, Science 2008, 321, 1188-1190;
50. f) Y. Zhang, K. Huynh, I. Manners, C.A. Reed, Chem. Commun. 2008, 494-496;
51. g) S. Duttwyler, Q.-Q. Do, A. Linden, K. K. Baldridge, J. S. Siegel, Angew. Chem. 2008, 120, 1743;
52. Angew. Chem. Int. Ed. 2008, 47, 1719-1722;
53. h) K.-C. Kim, C.A. Reed, D. W. Elliott, L. J. Mueller, F. Tham, L. Lin, J. B. Lambert, Science 2002, 297, 825-827;
54. i) C.A. Reed, Acc. Chem. Res. 1998, 31, 325-332.
55. J. Lacour, V. Hebbe-Viton, Angew. Chem. 2009, 121, 4427;
56. Angew. Chem. Int. Ed. 2009, 48, 4363-4366.
57. a) S. Mukherjee, B. List, J. Am. Chem. Soc. 2007, 129, 11336-11337;
58. b) G. L. Hamilton, E. J. Kang, M. Mba, D. Toste, Science 2007, 317, 496-499.
59. K. Hensen, T. Zengerly, P. Pickel, G. Klebe, Angew. Chem. 1983, 95, 739-739;
60. Angew. Chem. Int. Ed. Engl. 1983, 22, 725-726.
61. Z. Xie, D. J. Liston, T. Jelinek, V. Mitro, R. Bau, C. A. Reed, J. Chem. Soc. Chem. Commun. 1993, 384-386.
62. C. A. Reed, Z. Xie, R. Bau, A. Benesi, Science 1993, 262, 402-404.
63. T. Küppers, E. Bernhardt, R. Eujen, H. Willner, C. W. Lehmann, Angew. Chem. 2007, 119, 6462-6465;
64. Angew. Chem. Int. Ed. 2007, 46, 6346-6349.
65. R. D. Allen, T. E. Long, J. E. McGrath, Polym. Bull. 1986, 15, 127-134.
66. A. G. Massey, A. J. Park, J. Organomet. Chem. 1964, 2, 245-250.
67. SHELXTL, Version 6.12, Bruker Analytical X-ray Solutions, Madison, WI, 2001.
68. A. Rodriguez-Delgado, E. Y.-X. Chen, Macromolecules 2005, 38, 2587-2594.
69. a) A.D. Bolig, E. Y-X. Chen, J. Am. Chem. Soc. 2004, 126, 4897-4906;
70. b) A. Rodriguez-Delgado, W. R. Mariott, E. Y-X. Chen, Macromolecules 2004, 37, 3092-3100;
71. c) F. A. Bovey, P. A. Mirau, NMR of Polymers, Academic Press, San Diego, 1996;
72. d) R. Chújô, K. Hatada, R. Kitamaru, T. Kitayama, H. Sato, Y. Tanaka, Polym. J. 1987, 19, 413-424
73. a) W. R. Mariott, E. Y.-X. Chen, Macromolecules 2005, 38, 6822-6832;
74. b)W. R. Mariott, E. Y.-X. Chen, Macromolecules 2004, 37, 4741-4743;
75. c) M. Kobayashi, S. Okuyama, T. Ishizone, S. Nakahama, Macromolecules 1999, 32, 6466-6477;
76. d) X. Xie, T. E. HogenEsch, Macromolecules 1996, 29, 1746-1752;
77. e) A. Bulai, M. L. Jimeno, A.-A. de Queiroz, A. Gallardo, J. S. Roman, Macromolecules 1996, 29, 3240-3246.