Controlled radical polymerization of a styrenic sulfonium monomer and post-polymerization modifications

Polymer Chemistry

Volumn 4, Issue 6, 2013, Pages 2115-2124

  Borguet, Yannick P ^a   Tsarevsky, Nicolay V ^a  

^a SOUTHERN METHODIST UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; BLOCK COPOLYMERS; CHLORINE COMPOUNDS; FREE RADICAL POLYMERIZATION; IONIC LIQUIDS; MOLECULAR WEIGHT DISTRIBUTION; MONOMERS; POLYMERS; POLYSTYRENES; SODIUM;

ALKYL BROMIDES; BENZYLIC; BUILDING BLOCKES; CHAIN TRANSFER AGENTS; CHAIN-ENDS; CONTROLLED RADICAL POLYMERIZATION; EPOXIDE GROUPS; INITIATION EFFICIENCY; LOSS OF CONTROL; METHYLENE GROUPS; MONOMER CONVERSIONS; NARROW MOLECULAR WEIGHT DISTRIBUTIONS; POLYMERIZATION CONDITIONS; POST-POLYMERIZATION; REACTION MIXTURE; REVERSIBLE ADDITION FRAGMENTATION CHAIN TRANSFER; SODIUM AZIDE; SULFONIUM SALTS; TETRAFLUOROBORATES; TETRAHYDROTHIOPHENE; THIOETHERS; TRITHIOCARBONATE;

ATOM TRANSFER RADICAL POLYMERIZATION;

EID: 84874090308     PISSN: 17599954     EISSN: 17599962     Source Type: Journal    
DOI: 10.1039/c2py21106h     Document Type: Article

References (68)

1. A. von Oefele Justus Liebigs Ann. Chem. 1864 132 82 86
2. A. Cahours Compt. Rend. 1865 60 1147 1151
3. The Chemistry of the Sulphonium Group, ed., C. J. M. Stirling, Wiley, Chichester, 1981
4. Synthetic Applications of Sulfonium Salts and Sulfonium Ylides, ed., E. Block, 1981
5. K. Umemura H. Matsuyama N. Kamigata Bull. Chem. Soc. Jpn. 1990 63 2593 2600
6. J. Forrester R. V. H. Jones L. Newton P. N. Preston Tetrahedron 2001 57 2871 2884
7. B. M. Trost and L. S. Melvin, Jr, Organic Chemistry, Vol. 31: Sulfur Ylides, Emerging Synthetic Intermediates, Academic, 1975
8. Nitrogen, Oxygen and Sulfur Ylide Chemistry: A Practical Approach in Chemistry, ed., J. S. Clark, Oxford University Press, 2002
9. E. J. Corey M. Chaykovsky J. Am. Chem. Soc. 1962 84 3782 3783
10. E. J. Corey M. Chaykovsky J. Am. Chem. Soc. 1965 87 1353 1364
11. Y. G. Gololobov V. P. Lysenko I. E. Boldeskul Tetrahedron 1987 43 2609
12. J. V. Crivello Adv. Polym. Sci. 1984 62 1 48
13. J. V. Crivello J. Polym. Sci., Part A: Polym. Chem. 1999 37 4211 4254
14. T. Endo H. Uno J. Polym. Sci., Polym. Lett. Ed. 1985 23 359 363
15. H. Uno T. Endo Chem. Lett. 1986 15 1869 1870
16. H. Uno T. Takata T. Endo J. Polym. Sci., Part A: Polym. Chem. 1989 27 1675 1685
17. T. Endo H. Arita Makromol. Chem., Rapid Commun. 1985 6 137 139
18. K. Morio H. Murase H. Tsuchiya T. Endo J. Appl. Polym. Sci. 1986 32 5727 5732
19. A. Kikkawa T. Takata T. Endo Makromol. Chem. 1991 192 655 662
20. H. C. Kolb M. G. Finn K. B. Sharpless Angew. Chem., Int. Ed. 2001 40 2004 2021
21. C. R. Becer R. Hoogenboom U. S. Schubert Angew. Chem., Int. Ed. 2009 48 4900 4908
22. C. Barner-Kowollik F. E. Du Prez P. Espeel C. J. Hawker T. Junkers H. Schlaad W. Van Camp Angew. Chem., Int. Ed. 2011 50 60 62
23. M. F. Hoover J. Macromol. Sci., Part A 1970 4 1327 1418
24. Y. J. Kim H. Kang M. Leolukman P. F. Nealey P. Gopalan Chem. Mater. 2009 21 3030 3032
25. R. Kakuchi P. Theato Macromolecules 2012 45 1331 1338
26. W. A. Braunecker K. Matyjaszewski Prog. Polym. Sci. 2007 32 93 146
27. Controlled Radical Polymerization (ACS Symp. Ser. 685), ed., K. Matyjaszewski, ACS, Washington, DC, 1998
28. Controlled/Living Radical Polymerization. Progress in ATRP, NMP, and RAFT (ACS Symp. Ser. 768), ed., K. Matyjaszewski, ACS, Washington, DC, 2000
29. Advances in Controlled/Living Radical Polymerization (ACS Symp. Ser. 854), ed., K. Matyjaszewski, ACS, Washington, DC, 2003
30. Controlled/Living Radical Polymerization. From Synthesis to Materials (ACS Symp. Ser. 944), ed., K. Matyjaszewski, ACS, Washington, DC, 2006
31. Progress in Controlled Radical Polymerization: Mechanisms and Techniques (ACS Symp. Series 1100), ed., K. Matyjaszewski, B. S. Sumerlin, and, N. V. Tsarevsky, ACS, Washington, DC, 2012
32. Progress in Controlled Radical Polymerization: Materials and Applications (ACS Symp. Series 1101), ed., K. Matyjaszewski, B. S. Sumerlin, and, N. V. Tsarevsky, ACS, Washington, DC, 2012
33. Y. P. Borguet N. V. Tsarevsky Polym. Chem. 2012 3 2487 2494
34. K. Matyjaszewski W. Jakubowski K. Min W. Tang J. Huang W. A. Braunecker N. V. Tsarevsky Proc. Natl. Acad. Sci. U. S. A. 2006 103 15309 15314
35. T. Pintauer K. Matyjaszewski Chem. Soc. Rev. 2008 37 1087 1097
36. G. Moad E. Rizzardo S. H. Thang Aust. J. Chem. 2005 58 379 410
37. G. Moad Y. K. Chong A. Postma E. Rizzardo S. H. Thang Polymer 2005 46 8458 8468
38. S. Perrier P. Takolpuckdee J. Polym. Sci., Part A: Polym. Chem. 2005 43 5347 5393
39. Handbook of RAFT Polymerization, ed., C. Barner-Kowollik, Wiley-VCH, Weinheim, 2008
40. K. Skrabania A. Laschewsky H. v. Berlepsch C. Böttcher Langmuir 2009 25 7594 7601
41. J. U. Lind C. Acikgöz A. E. Daugaard T. L. Andresen S. Hvilsted M. Textor N. B. Larsen Langmuir 2012 28 6502 6511
42. W. T. Eckenhoff A. B. Biernesser T. Pintauer Inorg. Chem. 2012 51 11917 11929
43. H. Tagoshi T. Endo J. Polym. Sci., Part C: Polym. Lett. 1988 26 77 81
44. R. B. Sandin Chem. Rev. 1943 32 249 276
45. N. V. Tsarevsky K. Matyjaszewski Chem. Rev. 2007 107 2270 2299
46. S. R. Woodruff B. J. Davis N. V. Tsarevsky ACS Symp. Ser. 2012 1100 99 113
47. H. Tang J. Tang S. Ding M. Radosz Y. Shen J. Polym. Sci., Part A: Polym. Chem. 2005 43 1432 1443
48. N. V. Tsarevsky W. A. Braunecker S. J. Brooks K. Matyjaszewski Macromolecules 2006 39 6817 6824
49. C. Barner-Kowollik, in Handbook of RAFT Polymerization, Wiley-VCH Verlag GmbH & Co. KGaA, 2008, pp. 1-4
50. A. B. Lowe B. S. Sumerlin M. S. Donovan D. B. Thomas P. Hennaux C. L. McCormick ACS Symp. Ser. 2003 854 586 602
51. G. Moad E. Rizzardo S. H. Thang Aust. J. Chem. 2006 59 669 692
52. G. Moad E. Rizzardo S. H. Thang Aust. J. Chem. 2009 62 1402 1472
53. G. Moad E. Rizzardo S. H. Thang Aust. J. Chem. 2012 65 985 1076
54. C. L. McCormick A. B. Lowe Acc. Chem. Res. 2004 37 312 325
55. A. Gregory M. H. Stenzel Prog. Polym. Sci. 2012 37 38 105
56. A. B. Lowe C. L. McCormick Prog. Polym. Sci. 2007 32 283 351
57. K. K. Stokes J. A. Orlicki F. L. Beyer Polym. Chem. 2011 2 80 82
58. H. Willcock R. K. O'Reilly Polym. Chem. 2010 1 149 157
59. G. Moad E. Rizzardo S. H. Thang Polym. Int. 2011 60 9 25
60. M. A. Harvison P. J. Roth T. P. Davis A. B. Lowe Aust. J. Chem. 2011 64 992 1006
61. N. V. Tsarevsky K. Matyjaszewski Macromolecules 2002 35 9009 9014
62. J. M. Spruell B. A. Levy A. Sutherland W. R. Dichtel J. Y. Cheng J. F. Stoddart A. Nelson J. Polym. Sci., Part A: Polym. Chem. 2009 47 346 356
63. H. F. Gilbert Methods Enzymol. 1984 107 330 351
64. J. S. Carlson M. R. Hill T. Young P. J. Costanzo Polym. Chem. 2010 1 1423 1426
65. W. W. Cleland Biochemistry 1964 3 480 482
66. D. R. Edwards P. Montoya-Peleaz C. M. Crudden Org. Lett. 2007 9 5481 5484
67. A.-H. Li L.-X. Dai V. K. Aggarwal Chem. Rev. 1997 97 2341 2372
68. V. K. Aggarwal C. L. Winn Acc. Chem. Res. 2004 37 611 620