Postfunctionalization of polyoxanorbornene via sequential Michael addition and radical thiol-ene click reactions

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 50, Issue 15, 2012, Pages 3116-3125

  Durmaz, Hakan ^a   Butun, Muge ^a   Hizal, Gurkan ^a   Tunca, Umit ^a  

^a ISTANBUL TECHNICAL UNIVERSITY   (Turkey)

Author keywords

click reactions; Michael addition; nitroxide radical coupling reaction (NRC); NMR; photoinduced radical thiol ene reaction; poly(oxanorbornene imide) (PONB); ROMP; triple detection GPC (TD GPC)

Indexed keywords

CLICK REACTION; MICHAEL ADDITIONS; NITROXIDE RADICALS; POLY(OXANORBORNENE IMIDE) (PONB); ROMP; THIOL-ENE REACTIONS; TRIPLE DETECTION GPC (TD-GPC);

NUCLEAR MAGNETIC RESONANCE; RING OPENING POLYMERIZATION;

ADDITION REACTIONS;

EID: 84862732952     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.26098     Document Type: Article

References (61)

1. Sinnwell, S.,;, Inglis, A. J.,;, Stenzel, M. H.,;, Barner-Kowollik, C., In Click Chemistry for Biotechnology and Materials Science;, Lahann, J., Ed.; Wiley: Chichester, 2009; pp 89-117.
2. Lutz, J.-F., Angew. Chem. Int. Ed. 2007, 46, 1018-1025.
3. Meldal, M.,;, Tornoe, C. W., Chem. Rev. 2008, 108, 2952-3015.
4. Ouchi, M.,;, Terashima, T.,;, Sawamoto, M., Chem. Rev. 2009, 109, 4963-5050.
5. Iha, R. K.,;, Wooley, K. L.,;, Nystrom, A. M.,;, Burke, D. J.,;, Kade, M. J.,;, Hawker, C. J., Chem. Rev. 2009, 109, 5620-5686.
6. Becer, C. R.,;, Hoogenboom, R.,;, Schubert, U. S., Angew. Chem. Int. Ed. 2009, 48, 4900-4908.
7. Gao, H. F.,;, Matyjaszewski, K., Prog. Polym. Sci. 2009, 34, 317-350.
8. Sumerlin, B. S.,;, Vogt, A. P., Macromolecules 2010, 43, 1-13.
9. Altintas, O.,;, Tunca, U., Chem. Asian J. 2011, 6, 2584-2591.
10. (a), Hizal, G.,;, Tunca, U.,;, Sanyal, A., J. Polym. Sci. Part A: Polym. Chem. 2011, 49, 4103-4120
11. (b), Durmaz, H.,;, Sanyal, A.,;, Hizal, G.,;, Tunca, U., Polym. Chem. DOI: 10.1039/C1PY00471A.
12. Altintas, O.,;, Vogt, A. P.,;, Barner-Kowollik, C.,;, Tunca, U., Polym. Chem. 2012, 3, 34-45.
13. Kempe, K.,;, Krieg, A.,;, Becer, C. R.,;, Schubert, U. S., Chem. Soc. Rev. 2012, 41, 176-191.
14. (a), Dondoni, A., Angew. Chem. Int. Ed. 2008, 47, 8995-8997
15. (b), Hoyle, C. E.,;, Bowman, C. N., Angew. Chem. Int. Ed. 2010, 49, 1540-1573
16. (c), Hoogenboom, R., Angew. Chem. Int. Ed. 2010, 49, 3415-3417
17. (d), Hoyle, C. E.,;, Lowe, A. B.,;, Bowman, C. N., Chem. Soc. Rev. 2010, 39, 1355-1387
18. (e), Lowe, A. B., Polym. Chem. 2010, 1, 17-36
19. (f), Hall, D. J.,;, Van Den Berghe, H. M.,;, Dove, A. P., Polym. Int. 2011, 60, 1149-1157
20. (g), Kade, M. J.,;, Burke, D. J.,;, Hawker, C. J., J. Polym. Sci. Part A: Polym. Chem. Ed. 2010, 48, 743
21. (h), Uygun, M.,;, Tasdelen, M. A.,;, Yagci, Y., Macromol. Chem. Phys. 2010, 211, 103-110
22. (i), Roth, P. J.,;, Boyer, C.,;, Lowe, A. B.,;, Davis, T. P., Macromol. Rapid Commun. 2011, 32, 1123-1143.
23. Bielawski, C. W.,;, Grubbs, R. H., Prog. Polym. Sci. 2007, 32, 1-29.
24. Quemener, D.,;, Heroguez, V.,;, Gnanou, Y., In Macromolecular Engineering Precise Synthesis, Materials Properties, Applications, Matyjaszewski, K.,;, Gnanou, Y.,;, Leibler, L., Eds.; Wiley-VCH Verlag GmbH and Co. KGaA: Weinheim, Germany, 2007; Vol. 1, Chapter 7, pp 249-293.
25. Wallace, K. C.,;, Schrock, R. R., Macromolecules 1987, 20, 448-450.
26. Schrock, R. R.,;, Feldman, J.,;, Cannizzo, L. F.,;, Grubbs, R. H., Macromolecules 1987, 20, 1169-1172.
27. Cannizzo, L. F.,;, Grubbs, R. H., Macromolecules 1988, 21, 1961-1967.
28. Bazan, G. C.,;, Khosravi, E.,;, Schrock, R. R.,;, Feast, W. J.,;, Gibson, V. C., Polym. Commun. 1989, 30, 258-260.
29. Grubbs, R. H.,;, Tumas, W., Science 1989, 243, 907-915.
30. Bazan, G. C.,;, Khosravi, E.,;, Schrock, R. R.,;, Feast, W. J.,;, Gibson, V. C.,;, O'Regan, M. B.,;, Thomas, J. K.,;, Davis, W. M., J. Am. Chem. Soc. 1990, 112, 8378-8387.
31. Bazan, G. C.,;, Schrock, R. R., Macromolecules 1991, 24, 817-823.
32. Bielawski, C. W.,;, Morita, T.,;, Grubbs, R. H., Macromolecules 2000, 33, 678-680.
33. Owen, R. M.,;, Gestwicki, J. E.,;, Young, T.,;, Kiessling, L. L., Org. Lett. 2002, 4, 2293-2296.
34. Murphy, J.,;, Kawasaki, T.,;, Fujiki, M.,;, Nomura, K., Macromolecules 2005, 38, 1075-1083.
35. O'Reilly, R. K.,;, Joralemon, M. J.,;, Hawker, C. J.,;, Wooley, K. L., J. Polym. Sci. Part A: Polym. Chem. Ed. 2006, 44, 5203-5217.
36. Ma, J.,;, Cheng, C.,;, Sun, G. R.,;, Wooley, K. L., J. Polym. Sci. Part A: Polym. Chem. Ed. 2008, 46, 3488-3498.
37. Ma, J.,;, Cheng, C.,;, Sun, G. R.,;, Wooley, K. L., Macromolecules 2008, 41, 9080-9089.
38. Ma, J.,;, Cheng, C.,;, Wooley, K. L., Macromolecules 2009, 42, 1565-1573.
39. Jing, F.,;, Hillmyer, M. A., J. Am. Chem. Soc. 2008, 130, 13826-13827.
40. Kobayashi, S.,;, Pitet, L. M.,;, Hillmyer, M. A., J. Am. Chem. Soc. 2011, 133, 5794-5797.
41. (a), Kluger, C.,;, Binder, W. H., J. Polym. Sci. Part A: Polym. Chem. Ed. 2007, 45, 485-499
42. (b), Yang, S. K.,;, Weck, M., Macromolecules 2008, 41, 346-351
43. (c), Hilf, S.,;, Hanik, N.,;, Kilbinger, A. F. M., J. Polym. Sci. Part A: Polym. Chem. Ed. 2008, 46, 2913-2921
44. (d), Le, D.,;, Montembault, V.,;, Soutif, J.-C.,;, Rutnakornpituk, M.,;, Fontaine, L., Macromolecules 2010, 43, 5611-5617.
45. Xia, Y.,;, Kornfield, J. A.,;, Grubbs, R. H., Macromolecules 2009, 42, 3761-3766.
46. Le, D.,;, Montembault, V.,;, Soutif, J.-C.,;, Rutnakornpituk, M.,;, Fontaine, L., Macromolecules 2010, 43, 5611-5617.
47. (a), Gozgen, A.,;, Dag, A.,;, Durmaz, H.,;, Sirkecioglu, O.,;, Hizal, G.,;, Tunca, U., J. Polym. Sci. Part A: Polym. Chem. Ed. 2009, 47, 497-504
48. (b), Dag, A.,;, Durmaz, H.,;, Sirkecioglu, O.,;, Hizal, G.,;, Tunca, U., J. Polym. Sci. Part A: Polym. Chem. Ed. 2009, 47, 2344-2351.
49. Kolb, H. C.,;, Finn, M. G.,;, Sharpless, K. B., Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
50. Koo, S. P. S.,;, Stamenovic, M. M.,;, Prasath, R. A.,;, Inglis, A. J.,;, Du Prez, F. E.,;, Barner-Kowollik, C.,;, Van Camp, W.,;, Junkers, T., J. Polym. Sci. Part A: Polym. Chem. Ed. 2010, 48, 1699-1713.
51. Mather, B. D.,;, Viswanathan, K.,;, Miller, K. M.,;, Long, T. E., Prog. Polym. Sci. 2006, 31, 487-531.
52. (a), Durmaz, H.,;, Dag, A.,;, Cerit, N.,;, Sirkecioglu, O.,;, Hizal, G.,;, Tunca, U., J. Polym. Sci. Part A: Polym. Chem. Ed. 2010, 48, 5982-5991
53. (b), Dag, A.,;, Sahin, H.,;, Durmaz, H.,;, Hizal, G.,;, Tunca, U., J. Polym. Sci. Part A: Polym. Chem. Ed. 2011, 49, 886-892.
54. Cerit, N.,;, Cakir, N.,;, Dag, A.,;, Sirkecioglu, O.,;, Durmaz, H.,;, Hizal, G.,;, Tunca, U., J. Polym. Sci. Part A: Polym. Chem. Ed. 2011, 49, 2850-2858.
55. Wolfberger, A.,;, Rupp, B.,;, Kern, W.,;, Griesser, T.,;, Slugovc, C., Macromol. Rapid Commun. 2011, 32, 518-522.
56. Ma, J.,;, Cheng, C.,;, Wooley, K. L., Aust. J. Chem. 2009, 62, 1507-1519.
57. Stamenovic, M. M.,;, Espeel, P.,;, Van Camp, W.,;, Du Prez, F. E., Macromolecules 2011, 44, 5619-5630.
58. Mantovani, G.,;, Lecolley, F.,;, Tao, L.,;, Haddleton, D. M.,;, Clerx, J.,;, Cornellisen, J. J. L. M.,;, Velonia, K., J. Am. Chem. Soc. 2005, 127, 2966-2973.
59. Jia, Z.,;, Bell, C. A.,;, Monteiro, M. J., Macromolecules 2011, 44, 1747-1751.
60. Li, A.,;, Ma, J.,;, Wooley, K. L., Macromolecules 2009, 42, 5433-5436.
61. Kulis, J.,;, Bell, C. A.,;, Micallef, A. S.,;, Monteiro, M. J., J. Polym. Sci. Part A: Polym. Chem. Ed. 2010, 48, 2214-2223.