Ultrafast synthesis of ultrahigh molar mass polymers by metal-catalyzed living radical polymerization of acrylates, methacrylates, and vinyl chloride mediated by SET at 25 °C

Journal of the American Chemical Society

Volumn 128, Issue 43, 2006, Pages 14156-14165

  Percec, Virgil ^a   Guliashvili, Tamaz ^a   Ladislaw, Janine S ^a   Wistrand, Anna ^a   Stjerndahl, Anna ^a   Sienkowska, Monika J ^a   Monteiro, Michael J ^a   Sahoo, Sangrama ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; NITROGEN; POLYMERIZATION; POLYVINYL CHLORIDES; SOLVENTS; SYNTHESIS (CHEMICAL);

ATOM TRANSFER RADICAL POLYMERIZATION (ATRP); DIPOLAR APROTIC SOLVENTS; METHACRYLATES; RADICAL POLYMERIZATION; ULTRAFAST SYNTHESIS;

ACRYLICS;

ACRYLIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; ALKYL GROUP; COPPER; ETHYLENE; HALIDE; IONIC LIQUID; LIGAND; METHACRYLIC ACID DERIVATIVE; NITROGEN; POLYMER; PROPYLENE CARBONATE; RADICAL; SELENIUM DERIVATIVE; SOLVENT; SULFUR; TELLURIUM; VINYL CHLORIDE; WATER;

ARTICLE; ATOM TRANSFER RADICAL POLYMERIZATION; CATALYSIS; ELECTRON TRANSPORT; MOLECULAR WEIGHT; POLYMERIZATION; RADICAL REACTION; ROOM TEMPERATURE; SINGLE ELECTRON TRANSFER; SYNTHESIS;

EID: 33750445950     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065484z     Document Type: Article

References (97)

1. (a) Kato, M.; Kamigaito, M.; Sawamoto, M.; Higashimura, T. Macromolecules 1995, 28, 1721-1723.
2. (b) Wang, J. S.; Matyjaszewski, K. J. Am. Chem. Soc. 1995, 117, 5614-5615.
3. (c) Matyjaszewski, K.; Xia, J. Chem. Rev. 2001, 101, 2921-2990.
4. (d) Kamigaito, M.; Ando, T.; Sawamoto, M. Chem. Rev. 2001, 101, 3689-3746.
5. (e) Limer, A.; Haddleton, D. M. Prog. React. Kinet. 2004, 29, 187-241.
6. (f) Matyjaszewski, K. Macromol. Symp. 1998, 134, 105-118.
7. (g) Taube, H. Myers, H. J. Am. Chem. Soc. 1954, 76, 2103-2111.
8. (g) Taube, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 329-339.
9. (a) Percec, V.; Barboiu, B. Macromolecules 1995, 28, 7970-7972.
10. (b) Percec, V.; Barboiu, B.; Kim, H.-J. J. Am. Chem. Soc. 1998, 120, 305-316.
11. (c) Grigoras, C.; Percec, V. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 319-330.
12. (d) Percec, V.; Grigoras, C. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 3920-3931.
13. Percec, V.; Grigoras, C. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 5283-5299.
14. (a) Percec, V.; Grigoras, C. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 5609-5619.
15. (b) Kubisa, P. J. Prog. Polym. Sci. 2004, 29, 3-12.
16. (b) Kubisa, P. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 4675-4683.
17. Wayland, B. B.; Poszmik, G.; Mukerjee, S. L.; Fryd, M. J. Am. Chem. Soc. 1994, 116, 7943-7944.
18. Barboiu, B.; Percec, V. Macromolecules 2001, 34, 8626-8636.
19. (a) Percec, V.; Barboiu, B.; Grigoras, C.; Bera, T. K. J. Am. Chem. Soc. 2003, 125, 6503-6516.
20. (b) Percec, V.; Grigoras, C.; Kim, H.-J. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 505-513.
21. (c) Percec, V.; Grigoras, C.; Bera, T. K.; Barboiu, B.; Bissel, P. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 4894-4906.
22. (a) Fischer, H. Chem. Rev. 2001, 101, 3581-3610.
23. (b) Studer, A. Chem.-Eur. J. 2001, 7, 1159-1164.
24. Queffelec, J.; Gaynor, S. G.; Matyjaszewski, K. Macromolecules 2000, 33, 8629-8639.
25. (a) Stockland, R. A.; Jordan, R. F. J. Am. Chem. Soc. 2000, 122, 6315-6316.
26. (b) Stockland, R. A.; Foley, S. R.; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 796-809.
27. (c) Foley, S. R.; Stockland, R. A.; Shen, H.; Jordan, R. F. J. Am. Chem. Soc. 2003, 125, 4350-4361.
28. (a) Percec, V.; Popov, A. V.; Ramirez-Castillo, E.; Monteiro, M.; Barboiu, B.; Weichold, O.; Asandei, A. D.; Mitchell, C. M. J. Am. Chem. Soc. 2002, 124, 4940-4941.
29. (b) Percec, V.; Popov, A. V.; Ramirez-Castillo, E.; Weichold, O. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 3283-3299.
30. (c) Bunnett, J. F.; Scamehorn, R. G.; Traber, R. P. J. Org. Chem. 1976, 41, 3677-3682.
31. (d) Jordan, R. B. Reaction Mechanisms of Inorganic and Organometalic Systems; Oxford University Press: Oxford, U.K., 1991; pp 168 and 183.
32. (a) Luther, R. Z. Physik. Chem. 1901, 36, 385.
33. (b) Fenwick, F. J. Am. Chem. Soc. 1926, 48, 860-870.
34. (c) Tindall, G. W.; Bruckenstein, S. Anal. Chem. 1968, 40, 1402-1404.
35. (d) Ciavatta, L.; Ferri, D.; Palombari, R. J. Inorg. Nucl. Chem. 1980, 42, 593-598.
36. (e) Solari, E.; Latronico, M.; Blech, P.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Inorg. Chem. 1996, 35, 4526-4528.
37. (f) Hataway, B. J. In Comprehensive Coordination Chemistry, Wikinson, G., Gillard, R. B., McCleverty, J. A., Eds.; Pergamon: Oxford, U.K., 1987; Vol. 5, pp 533-774.
38. (g) Shriver, D.; Atkins, P. Inorganic Chemistry, 3rd ed.; Freeman, New York, 1999; pp 195-196.
39. (a) Kong, J. et al. J. Comput. Chem. 2000, 21, 1532-1548.
40. (b) Gillies, M. B.; Matyjaszewski, K.; Norrby, P.-O.; Pintauer, T.; Poli, R.; Richard, P. Macromolecules 2003, 36, 8551-8559.
41. (a) Chen, Q.-Y. Isr. J. Chem. 1999, 39, 179-192.
42. (b) Sato, K.; Nakazato, S.; Enko, H.; Tsujita, H.; Yamamoto, T.; Omote, M.; Ando, A.; Kumadaki, I. J. Fluorine Chem. 2003, 121, 105-107.
43. (c) Sato, K.; Ogawa, Y.; Tamura, M.; Harada, M.; Ohara, T.; Omote, M.; Ando, A.; Kumadaki, I. Collect. Czech. Chem. Commun. 2002, 67, 1285-1295.
44. (d) Brace, N. O. J. Fluorine Chem. 2001, 108, 147-175.
45. (a) Percec, V.; Barboiu, B.; van der Sluis, M. Macromolecules 1998, 31, 4053-4053.
46. (b) Percec, V.; Asandei, A. D.; Asgarzadeh, F.; Bera, T. K.; Barboiu, B. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 3839-3843.
47. (c) Percec, V.; Barboiu, B.; Bera, T. K.; van der Sluis, M.; Grubbs, R. B.; Fréchet, J. M. J. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 4776-4791.
48. (d) van der Sluis, M.; Barboiu, B.; Pesa, N.; Percec, V. Macromolecules 1998, 31, 9409-9412.
49. (e) Percec, V.; Kim, H.-J.; Barboiu, B. Macromolecules 1997, 30, 6702-6705.
50. (f) Robello, D. R.; André, A.; McCovic, T. A.; Krana, A.; Mourey, T. H. Macromolecules 2002, 35, 9334-9344.
51. Haddleton, D. M.; Jasieczek, C. B.; Hannon, M. J.; Shooter, A. J. Macromolecules 1997, 30, 2190-2193.
52. (a) Howes, K. R.; Bakac, A.; Espenson, J. H. Inorg. Chem. 1988, 27, 3147-3151.
53. (b) Matyjaszewski, K.; Paik, H.-j.; Zhou, P.; Diamanti, S. J. Macromolecules 2001, 34, 5125-5131.
54. Marzilli, L. G.; Marzilli, P. A.; Halpern, J. J. Am. Chem. Soc. 1970, 92, 5752-5753.
55. (a) Matyjaszewski, K.; Coca, S.; Gaynor, S. G.; Wei, M.; Woodworth, B. E. Macromolecules 1997, 30, 7348-7350.
56. (b) Woodworth, B. E.; Metzner, Z.; Matyjaszewski, K. Macromolecules 1998, 31, 7999-8004.
57. (c) Cheng, G. L.; Hu, C. P.; Ying, S. K. J. Mater. Catal. A: Chem. 1999, 144, 357-362.
58. (d) Johnson, R. M.; Ng, C.; Samson, C. C. M.; Fraser, C. L. Macromolecules 2000, 33, 8618-8628.
59. (a) Xue, L.; Agarwal, U. S.; Lemstra, P. J. Macromolecules 2002, 35, 8650-8652.
60. (b) Wayland, B. B.; Basickes, L.; Mukerjee, S.; Wei, M.; Fryd, M. Macromolecules 1997, 30, 8109-8112.
61. (c) Percec, V.; Ramirez-Castillo, E.; Popov, A. V.; Hinojosa-Falcon, L.; Guliashvili, T. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 2178-2184.
62. (a) Farcet, C.; Belleney, J.; Charleux, B.; Pirri, R. Macromolecules 2002, 335, 4912-4918.
63. (b) Plessis, C.; Arzamendi, G.; Alberdi, J. M.; van Herk, A. M.; Leiza, J. R.; Asua, J. M. Makromol. Chem., Rapid Commun. 2003, 24, 173-177.
64. (a) Boyle, R. E. J. Org. Chem. 1966, 31, 3880-3882.
65. (b) Gurr, P. A.; Mills, M. F.; Qiao, G. G.; Solomon, D. H. Polymer 2005, 46, 2097-2104.
66. (a) Pause, L.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2000, 122, 9829-9835.
67. (b) Cardinale, A.; Isse, A. A.; Gennaro, A.; Rosset, M.; Savéant, J.-M. J. Am. Chem. Soc. 2002, 124, 13533-13539.
68. (c) Costentin, C.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2003, 125, 10729-10739.
69. (a) Robinson, K. L.; Khan, M. A.; de Paz Banez, M. V.; Wang, X. S.; Armes, S. P. Macromolecules 2001, 34, 3155-3158.
70. (b) Wang, X.-S.; Armes, S. P. Macromolecules 2000, 33, 6640-6647.
71. (c) Wang, X.-S.; Lascelles, S. F.; Jackson, R. A.; Armes, S. P. Chem. Commun. 1999, 1817-1818.
72. (d) Wang, X.-S.; Jackson, R. A.; Armes, S. P. Macromolecules 2000, 33, 255-257.
73. (e) Zeng, F.; Shen, Y.; Zhu, S. S.; Pelton, R. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 3821 -3827.
74. (f) Bontempo, D.; Maynard, H. D. J. Am. Chem. Soc. 2005, 127, 6508-6509.
75. (g) Lobb, E. J.; Ma, I.; Billingham, N. C.; Armes, S. P. J. Am. Chem. Soc. 2001, 123, 7913-7914.
76. (h) McDonald, S.; Rannard, S. P. Macromolecules 2001, 34, 8600-8602.
77. (i) Kimani, S. M.; Moratti, S. C. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 1588-1598.
78. (j) Bontempo, D.; Heredia, K. L.; Fish, B. A.; Maynard, H. D. J. Am. Chem. Soc. 2004, 126, 15372-15373.
79. (k) Perrier, S.; Gemici, H.; Li, S. Chem. Commun. 2004, 604-605.
80. (l) Percec, V.; Guliashvili, T.; Popov, A. V. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 1948-1954.
81. (m) Percec, V.; Guliashvili, T.; Popov, A. V.; Ramirez-Castillo, E. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 1935-1947.
82. (n) Percec, V.; Guliashvili, T.; Popov, A. V.; Ramirez-Castillo, E.; Hinojosa-Falcon, L. A. Polym. Sci., Part A: Polym. Chem. 2005, 43, 1660-1669.
83. (o) Percec, V.; Guliashvili, T.; Popov, A. V.; Ramirez-Castillo, E.; Coelho, J. F. J.; Hinojosa-Falcon, L. A. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 1649-1659.
84. (p) Bontempo, D.; Li, R. C.; Ly, T.; Brubaker, C. E.; Maynard, H. D. Chem. Commun. 2005, 4702-4704.
85. (q) Monge, S.; Darcos, V.; Haddleton, D. M. J. Polym. Sci. Part A: Polym. Chem. 2004, 42, 6299-6308.
86. (r) Mao, B. W.; Gan, L. H.; Gan, Y. Y. Polymer 2006, 47, 3017-3020.
87. (a) Bellus, D. Pure Appl. Chem. 1985, 57, 1287-1838.
88. (b) Pirrung, F. O. H.; Hiemstra, H.; Speckamp, W. N.; Kaptein, B.; Schoemaker, H. E. Synthesis 1995, 458-472.
89. (c) Iqbal, J.; Bhatia, B.; Navyar, N. K. Chem. Rev. 1994, 94, 519-564.
90. (d) Kamigata, N.; Shimizu, T. Rev. Heteroat. Chem. 1997, 17, 1-50.
91. (e) Gossage, R. A.; van de Kuil, L. A.; van Koten, G. Acc. Chem. Res. 1998, 31, 423-431.
92. (f) Clark, A. J. Chem. Soc. Rev. 2002, 31, 1-11.
93. (g) Delaude, L.; Demonceau, A.; Noels, A. F. Top. Organomet. Chem. 2004, 11, 155-171.
94. (h) Severin, K. Curr. Org. Chem. 2006, 10, 217-224.
95. (i) Quebatte, L.; Thommes, K.; Severin, K. J. Am. Chem. Soc. 2006, 128, 7440-7441.
96. (a) Min, K.; Gao, H.; Matyjaszewski, K. J. Am. Chem. Soc. 2005, 127, 3825-3830.
97. (b) Jakubowski, W.; Min, K.; Matyjaszewski, K. Macromolecules 2006, 39, 39-45.