Alternating copolymerization by nitroxide-mediated polymerization and subsequent orthogonal functionalization

Angewandte Chemie - International Edition

Volumn 54, Issue 17, 2015, Pages 5054-5059

  Tesch, Matthias ^a   Hepperle, Johannes A M ^a   Klaasen, Henning ^a   Letzel, Matthias ^a   Studer, Armido ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

active esters; alternating polymerization; nitroxide mediated polymerization; orthogonal functionalization; thiol ene reactions

Indexed keywords

COPOLYMERS; LIBRARIES; POLYMERIZATION; POLYMERS;

ACTIVE ESTERS; ALTERNATING COPOLYMER; ALTERNATING COPOLYMERIZATION; FUNCTIONALIZATIONS; NITROXIDE MEDIATED POLYMERIZATION; POLYMER ANALOGOUS REACTION; THIOL-ENE CLICK REACTIONS; THIOL-ENE REACTIONS;

COPOLYMERIZATION;

ACRYLIC ACID; ACRYLIC ACID DERIVATIVE; NITROGEN OXIDE; NITROXYL; POLYMER; THIOL DERIVATIVE; VINYL DERIVATIVE; VINYL ETHER;

CHEMISTRY; CLICK CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; SYNTHESIS;

ACRYLATES; CLICK CHEMISTRY; MAGNETIC RESONANCE SPECTROSCOPY; NITROGEN OXIDES; POLYMERIZATION; POLYMERS; SULFHYDRYL COMPOUNDS; VINYL COMPOUNDS;

EID: 84927758592     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201412206     Document Type: Article

References (70)

1. N. Badi, J.-F. Lutz, Chem. Soc. Rev. 2009, 38, 3383-3390
2. J.-F. Lutz, Nat. Chem. 2010, 2, 84-85
3. J.-F. Lutz, Polym. Chem. 2010, 1, 55-62
4. M. Ouchi, N. Badi, J.-F. Lutz, M. Sawamoto, Nat. Chem. 2011, 3, 917-924
5. J.-F. Lutz, M. Ouchi, D. R. Liu, M. Sawamoto, Science 2013, 341, 628-637.
6. S. Pfeifer, J.-F. Lutz, J. Am. Chem. Soc. 2007, 129, 9542-9543
7. S. Ida, T. Terashima, M. Ouchi, M. Sawamoto, J. Am. Chem. Soc. 2009, 131, 10808-10809
8. M. L. McKee, P. J. Milnes, J. Bath, E. Stulz, A. J. Turberfield, R. K. O'Reilly, Angew. Chem. Int. Ed. 2010, 49, 7948-7951
9. Angew. Chem. 2010, 122, 8120-8123
10. Y. Hibi, M. Ouchi, M. Sawamoto, Angew. Chem. Int. Ed. 2011, 50, 7434-7437
11. Angew. Chem. 2011, 123, 7572-7575
12. A. H. Soeriyadi, C. Boyer, F. Nyström, P. B. Zetterlund, M. R. Whittaker, J. Am. Chem. Soc. 2011, 133, 11128-11131
13. N. Baradel, S. Fort, S. Halila, N. Badi, J.-F. Lutz, Angew. Chem. Int. Ed. 2013, 52, 2335-2339
14. Angew. Chem. 2013, 125, 2391-2395
15. J. Vandenbergh, G. Reekmans, P. Adriaensens, T. Junkers, Chem. Commun. 2013, 49, 10358-10360
16. D. Yamamoto, A. Matsumoto, Macromolecules 2013, 46, 9526-9536
17. M. Hisano, T. Takashima, Z. Jin, A. Shiibashi, A. Matsumoto, Macromol. Chem. Phys. 2013, 214, 1612-1620
18. S. C. Solleder, M. A. R. Meier, Angew. Chem. Int. Ed. 2014, 53, 711-714
19. Angew. Chem. 2014, 126, 729-732.
20. C. J. Hawker, A. W. Bosman, E. Harth, Chem. Rev. 2001, 101, 3661-3688
21. K. Matyjaszewski, J. Xia, Chem. Rev. 2001, 101, 2921-2990
22. C. Barner-Kowollik, T. P. Davis, J. P. A. Heuts, M. H. Stenzel, P. Vana, M. Whittaker, J. Polym. Sci. Polym. Chem. 2003, 41, 365-375
23. A. Studer, Chem. Soc. Rev. 2004, 33, 267-273
24. A. Studer, T. Schulte, Chem. Rec. 2005, 5, 27-35
25. M. K. Brinks, A. Studer, Macromol. Rapid Commun. 2009, 30, 1043-1057
26. L. Tebben, A. Studer, Angew. Chem. Int. Ed. 2011, 50, 5034-5068
27. Angew. Chem. 2011, 123, 5138-5174
28. R. B. Grubbs, Polym. Rev. 2011, 51, 104-137.
29. D. Benoit, C. J. Hawker, E. E. Huang, Z. Lin, T. P. Russell, Macromolecules 2000, 33, 1505-1507
30. G.-Q. Chen, Z.-Q. Wu, J.-R. Wu, Z.-C. Li, F.-M. Li, Macromolecules 1999, 32, 232-234
31. E. Chernikova, P. Terpugova, C. Bui, B. Charleux, Polymer 2003, 44, 4101-4107; see also Ref. [2 h]
32. S. Niu, M. Ding, M. Chen, T. Feng, L. Zhang, L. Wei, Z. Cheng, X. Zu, J. Polym. Sci. Polym. Chem. 2013, 51, 5263-5269
33. E. G. L. Williams, B. Fairbanks, G. Moad, R. G. Mulder, E. Rizzardo, S. H. Thang, Polym. Chem. 2015, 6, 228-232.
34. B. Kbox drawings light down and leftrcbox drawings light down and left, J.-F. Lutz, K. Matyjaszewski, Macromolecules 2002, 35, 2448-2451.
35. E. Mishima, S. Yamago, Macromol. Rapid Commun. 2011, 32, 893-898
36. E. Mishima, S. Yamago, J. Polym. Sci. Part A 2012, 50, 2254-2264.
37. I. I. Yilmaz, M. Arslan, A. Sanyal, Macromol. Rapid Commun. 2012, 33, 856-862
38. J. Budhathoki-Uprety, J. F. Reuther, B. M. Novak, Macromolecules 2012, 45, 8155-8165; for a review, see
39. K. A. Günay, P. Theato, H.-A. Klok, J. Polym. Sci. Part A 2013, 51, 1-28.
40. A. C. Engler, J. M. W. Chan, D. J. Coady, J. M. O'Brien, H. Sardon, A. Nelson, D. P. Sanders, Y. Y. Yang, J. L. Hedrick, Macromolecules 2013, 46, 1283-1290
41. K. Nilles, P. Theato, J. Polym. Sci. Part A 2010, 48, 3683-3692
42. K. A. Günay, N. Schüwer, H.-A. Klok, Polym. Chem. 2012, 3, 2186-2192.
43. C. E. Hoyle, C. N. Bowman, Angew. Chem. Int. Ed. 2010, 49, 1540-1573
44. Angew. Chem. 2010, 122, 1584-1617
45. A. Dondoni, Angew. Chem. Int. Ed. 2008, 47, 8995-8997
46. Angew. Chem. 2008, 120, 9133-9135; for recent examples, see
47. K. Kempe, R. Hoogenboom, M. Jaeger, U. S. Schubert, Macromolecules 2011, 44, 6424-6432
48. S. Tempelaar, L. Mespouille, P. Dubois, A. P. Dove, Macromolecules 2011, 44, 2084-2091
49. A. Gress, A. Völkel, H. Schlaad, Macromolecules 2007, 40, 7928-7933.
50. S. De Sarkar, A. Studer, Org. Lett. 2010, 12, 1992-1995
51. R. C. Samanta, S. De Sarkar, R. Fröhlich, S. Grimme, A. Studer, Chem. Sci. 2013, 4, 2177-2184
52. J. A. M. Hepperle, R. C. Samanta, A. Studer, Synlett 2013, 1233-1237.
53. S. Miele, P. Nesvadba, A. Studer, Macromolecules 2009, 42, 2419-2427
54. J. A. M. Hepperle, H. Luftmann, A. Studer, J. Polym. Sci. Part A 2012, 50, 2150-2160.
55. C. N. McEwen, P. M. Peacock, Anal. Chem. 2002, 74, 2743-2748
56. I. C. Wienhöfer, H. Luftmann, A. Studer, Macromolecules 2011, 44, 2510-2523
57. M. W. F. Nielen, Mass Spectrom. Rev. 1999, 18, 309-344
58. G. Hart-Smith, C. Barner-Kowollik, Macromol. Chem. Phys. 2010, 211, 1507-1529
59. G. Montaudo, F. Samperi, M. S. Montaudo, Prog. Polym. Sci. 2006, 31, 277-357
60. A. H. Soeriyadi, M. R. Whittaker, C. Boyer, T. P. Davis, J. Polym. Sci. Part A 2013, 51, 1475-1505.
61. C. Barner-Kowollik, F. E. De Prez, P. Espeel, C. J. Hawker, T. Junkers, H. Schlaad, W. Van Camp, Angew. Chem. Int. Ed. 2011, 50, 60-62
62. Angew. Chem. 2011, 123, 61-64.
63. M. Buback, A. Feldermann, C. Barner-Kowollik, I. Lacik, Macromolecules 2001, 34, 5439-5448.
64. S. Marque, H. Fischer, E. Baier, A. Studer, J. Org. Chem. 2001, 66, 1146-1156. Indeed, a model compound mimicking a polymer bearing a NBVE moiety as the ultimate monomer did not undergo C-O bond homolysis at 100 °C (see the Supporting Information).
65. The reason for the difference in the kinetic properties of the saturated and unsaturated systems could not be elucidated thus far. We hypothesize that it might be caused by a change in the monomer aggregation state. This is known for acrylate monomers, but has not be reported for vinyl ethers; see:, A. P. Haehnel, M. Schneider-Baumann, L. Arens, A. M. Misske, F. Fleischhaker, C. Barner-Kowollik, Macromolecules 2014, 47, 3483-3496.
66. K. Yamada, T. Nakano, Y. Okamoto, J. Polym. Sci. Part A 1999, 37, 2677-2683
67. Y. Isobe, K. Yamada, T. Nakano, Y. Okamoto, J. Polym. Sci. Part A 2000, 38, 4693-4703
68. K. Koumura, K. Satoh, M. Kamigaito, Macromolecules 2009, 42, 2497-2504
69. E. Mishima, T. Tamura, S. Yamago, Macromolecules 2012, 45, 2989-2994
70. E. Mishima, T. Tamura, S. Yamago, Macromolecules 2012, 45, 8998-9003.