Acrylamide-based copolymers bearing photoreleasable thiols for subsequent thiol-ene functionalization

Macromolecules

Volumn 45, Issue 4, 2012, Pages 1792-1802

  Delaittre, Guillaume ^a   Pauloehrl, Thomas ^a   Bastmeyer, Martin ^a   Barner Kowollik, Christopher ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLAMIDES; CO-MONOMER; CONTROLLED/LIVING RADICAL POLYMERIZATION; DEPROTECTION; FUNCTIONALIZATIONS; H NMR SPECTROSCOPY; HYDROPHOBIC BLOCKS; MALEIMIDES; N ,N-DIMETHYLACRYLAMIDE; N-ISOPROPYLACRYLAMIDES; POLYMERIZATION KINETICS; PROTECTING GROUP; QUANTITATIVE YIELDS; RADICAL POLYMERS; RAFT-MEDIATED POLYMERIZATION; REVERSIBLE ADDITION-FRAGMENTATION TRANSFERS; THERMO SENSITIVE; THIOL SPECIES; THIOL-ENES; WATER SOLUBLE COPOLYMERS; WATER-SOLUBLE BLOCK;

AMIDES; BLOCK COPOLYMERS; FREE RADICAL POLYMERIZATION; POLYSTYRENES;

ACRYLIC MONOMERS;

EID: 84857515108     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma202670d     Document Type: Article

References (92)

1. Hawker, C. J.; Wooley, K. L. Science 2005, 309, 1200
2. Binder, W. H.; Sachsenhofer, R. Macromol. Rapid Commun. 2007, 28, 15
3. Barner-Kowollik, C.; Inglis, A. J. Macromol. Chem. Phys. 2009, 210, 987
4. Iha, R. K.; Wooley, K. L.; Nystrom, A. N.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Chem. Rev. 2009, 109, 5620
5. Golas, P. L.; Matyjaszewski, K. Chem. Soc. Rev. 2010, 39, 1338
6. Sumerlin, B. S.; Vogt, A. P. Macromolecules 2010, 43, 1
7. Barner-Kowollik, C.; Du Prez, F. E.; Espeel, P.; Hawker, C. J.; Junkers, T.; Schlaad, H.; Van Camp, W. Angew. Chem., Int. Ed. 2011, 50, 60
8. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004
9. Meldal, M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952
10. Lutz, J.-F. Angew. Chem., Int. Ed. 2007, 46, 1018
11. Dirks, A. J.; Cornelissen, J. J. L. M.; van Delft, F. L.; van Hest, J. C. M.; Nolte, R. J. M.; Rowan, A. E.; Rutjes, F. P. J. T. QSAR Comb. Sci. 2007, 26, 1200
12. Meldal, M. Macromol. Rapid Commun. 2008, 29, 1016
13. Lundberg, P.; Hawker, C. J.; Hult, A.; Malkoch, M. Macromol. Rapid Commun. 2008, 29, 998
14. Aragão-Leoneti, V.; Campo, V. L.; Gomes, A. S.; Field, R. A.; Carvalho, I. Tetrahedron 2010, 66, 9475
15. Hoyle, C. E.; Bowman, C. N. Angew. Chem., Int. Ed. 2010, 49, 1540
16. Hoogenboom, R. Angew. Chem., Int. Ed. 2010, 49, 3415
17. Hoyle, C. E.; Lowe, A. B.; Bowman, C. N. Chem. Soc. Rev. 2010, 39, 1355
18. Sinnwell, S.; Inglis, A. J.; Davis, T. P.; Stenzel, M. H.; Barner-Kowollik, C. Chem. Commun. 2008, 2052
19. Inglis, A. J.; Sinnwell, S.; Stenzel, M. H.; Barner-Kowollik, C. Angew. Chem., Int. Ed. 2009, 48, 2411
20. Nebhani, L.; Gerstel, P.; Atanasova, P.; Bruns, M.; Barner-Kowollik, C. J. Polym. Sci., Polym. Chem. 2009, 47, 7090
21. Paulöhrl, T.; Inglis, A. J.; Barner-Kowollik, C. Adv. Mater. 2010, 22, 2788
22. Inglis, A. J.; Nebhani, L.; Altintas, O.; Schmidt, F.-G.; Barner-Kowollik, C. Macromolecules 2010, 43, 5515
23. Goldmann, A. S.; Tischer, T.; Barner, L.; Bruns, M.; Barner-Kowollik, C. Biomacromolecules 2011, 12, 1137
24. Ott, C.; Hoogenboom, R.; Schubert, U. S. Chem. Commun. 2008, 3516
25. Becer, C. R.; Babiuch, K.; Pilz, D.; Hornig, S.; Heinze, T.; Gottschaldt, M.; Schubert, U. S. Macromolecules 2009, 42, 2387
26. Babiuch, K.; Becer, C. R.; Gottschaldt, M.; Delaney, J. T.; Weisser, J.; Beer, B.; Wyrwa, R.; Schnabelrauch, M.; Schubert, U. S. Macromol. Biosci. 2011, 11, 535
27. Li, R. C.; Broyer, R. M.; Maynard, H. D. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 5004
28. Heredia, K. L.; Maynard, H. D. Org. Biomol. Chem. 2007, 5, 45
29. Heredia, K. L.; Tolstyka, Z. P.; Maynard, H. D. Macromolecules 2007, 40, 4772
30. Kopping, J. T.; Tolstyka, Z. P.; Maynard, H. D. Macromolecules 2007, 40, 8593
31. Christman, K. L.; Broyer, R. M.; Schopf, E.; Kolodziej, C. M.; Chen, Y.; Maynard, H. D. Langmuir 2011, 27, 4715
32. Singh, I.; Zarafshani, Z.; Lutz, J.-F.; Heaney, F. Macromolecules 2009, 42, 5411
33. Singh, I.; Zarafshani, Z.; Heaney, F.; Lutz, J.-F. Polym. Chem. 2011, 2, 372
34. Tsarevsky, N. V.; Bencherif, S. A.; Matyjaszewski, K. Macromolecules 2007, 40, 4439
35. Kade, M. J.; Burke, D. J.; Hawker, C. J. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 743
36. Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzzo, R. G.; Whitesides, G. M. Chem. Rev. 2005, 105, 1103
37. Ueda, A.; Nagai, S. In Polymer Handbook, 4 th ed.; Brandrup, J.; Immergut, E. H.; Grulke, E. A., Eds.; Wiley: New York, 1999; p II/97.
38. Chiefari, J.; Rizzardo, E. In Handbook of Radical Polymerization, 2 nd ed.; Matyjaszewski, K.; Davis, T. P., Eds.; John Wiley and Sons: New York, 2002; p 629.
39. Nagel, B.; Gajovic-Eichelmann, N.; Scheller, F. W.; Katterle, M. Langmuir 2010, 26, 9088
40. Crownover, E. F.; Convertine, A. J.; Stayton, P. S. Polym. Chem. 2011, 2, 1499
41. Bontempo, D.; Heredia, K. L.; Fish, B. A.; Maynard, H. D. J. Am. Chem. Soc. 2004, 126, 15372
42. Heredia, K. L.; Bontempo, D.; Ly, T.; Byers, J. T.; Halstenberg, S.; Maynard, H. D. J. Am. Chem. Soc. 2005, 127, 16955
43. Iwasaki, Y.; Omichi, Y.; Iwata, R. Langmuir 2008, 24, 8427
44. Vázquez-Dorbatt, V.; Tolstyka, Z. P.; Chang, C.-W.; Maynard, H. D. Biomacromolecules 2009, 10, 2207
45. Liu, J.; Bulmus, V.; Barner-Kowollik, C.; Stenzel, M. H.; Davis, T. P. Macromol. Rapid Commun. 2007, 28, 303
46. Boyer, C.; Liu, J.; Wong, L.; Tippett, M.; Bulmus, V.; Davis, T. P. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 7207
47. Chang, C.-W.; Nguyen, T. H.; Maynard, H. D. Macromol. Rapid Commun. 2010, 31, 1691
48. van Dijk-Wolthuis, W. N. E.; van de Wetering, P.; Hinrichs, W. L. J.; Hofmeyer, L. J. F.; Liskamp, R. M. J.; Crommelin, D. J. A.; Hennink, W. E. Bioconjug. Chem. 1999, 10, 687
49. Tsarevsky, N. V.; Matyjaszewski, K. Macromolecules 2002, 35, 9009
50. Li, L.; Jiang, X.; Zhuo, R. J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 5989
51. Carrot, G.; Hilborn, J.; Hedrick, J. L.; Trollsås, M. Macromolecules 1999, 32, 5171
52. Ye, M.; Zhang, D.; Han, L.; Tejada, J.; Ortiz, C. Soft Matter 2006, 2, 243
53. Javakhishvili, I.; Hvilsted, S. Biomacromolecules 2009, 10, 74
54. Hill, N. L.; Jarvis, J. L.; Pettersson, F.; Braslau, R. React. Funct. Polym. 2008, 68, 361
55. Barner, L.; Perrier, S. In Handbook of RAFT Polymerization; Barner-Kowollik, C.; Wiley-VCH: Weinheim, 2008; p 455.
56. Willcock, H.; O'Reilly, R. K. Polym. Chem. 2010, 1, 149
57. Moad, G.; Rizzardo, E.; Thang, S. H. Polym. Int. 2011, 60, 9
58. Garamszegi, L.; Donzel, C.; Carrot, G.; Nguyen, T. Q.; Hilborn, J. React. Funct. Polym. 2003, 55, 179
59. Uygun, M.; Tasdelen, M. A.; Yagci, Y. Macromol. Chem. Phys. 2010, 211, 103
60. Boyer, C.; Soeriyadi, A. H.; Roth, P. J.; Whittaker, M. R.; Davis, T. P. Chem. Commun. 2011, 47, 1318
61. Liras, M.; García, O.; Quijada-Garrido, I.; París, R. Macromolecules 2011, 44, 1335
62. Greene's Protective Groups in Organic Synthesis; Wuts, P. G. M.; Greene, T. W., Eds.; John Wiley and Sons: New York, 2007.
63. Pauloehrl, T.; Delaittre, G.; Bastmeyer, M.; Barner-Kowollik, C. Polym. Chem. 2012, 10.1039/C1PY00372K
64. Kostiainen, M. A.; Smith, D. K.; Ikkala, O. Angew. Chem., Int. Ed. 2007, 46, 7600-7604
65. Kostiainen, M. A.; Kasyutich, O.; Cornelissen, J. J. L. M.; Nolte, R. J. M. Nature Chem. 2010, 2, 394-399
66. Braun, F.; Eng, L.; Trogisch, S.; Voit, B. Macromol. Chem. Phys. 2003, 204, 1486
67. Ryan, D.; Parviz, B. A.; Linder, V.; Semetey, V.; Sia, S. K.; Su, J.; Mrksich, M.; Whitesides, G. M. Langmuir 2004, 20, 9080
68. Brown, A. A.; Azzaroni, O.; Huck, W. T. S. Langmuir 2009, 25, 1744
69. Aoyagi, B.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 3702
70. Bivigou-Koumba, A. M.; Kristen, J.; Laschewsky, A.; Mueller-Buschbaum, P.; Papadakis, C. M. Macromol. Chem. Phys. 2009, 210, 565
71. Clevenger, R. C.; Turnbull, K. D. Synth. Commun. 2000, 30, 1379
72. Gosh, S.; Tochtrop, G. P. Tetrahedron Lett. 2009, 50, 1723
73. Strazielle, C.; Benoit, H.; Vogl, O. Eur. Polym. J. 1978, 14, 331
74. Bajpai, U. D. N.; Bajpai, A. K.; Bajpai, J. J. Appl. Polym. Sci. 1991, 42, 2005
75. Schumers, J.-M.; Fustin, C.-A.; Can, A.; Hoogenboom, R.; Schubert, U. S.; Gohy, J.-F. J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 6504-6513
76. Greene, A. C.; Grubbs, R. B. Macromolecules 2010, 43, 10320
77. Nakayama, Y.; Matsuda, T. Langmuir 1999, 15, 5560
78. Il'ichev, Y. V.; Schwörer, M. A.; Wirz, J. J. Am. Chem. Soc. 2004, 126, 4581
79. Marriott, G.; Miyata, H.; Kinosita, K. Biochem. Int. 1992, 26, 943
80. Nagasaki, Y.; Okada, T.; Scholz, C.; Iijima, M.; Kato, M.; Kataoka, K. Macromolecules 1998, 31, 1473
81. Lu, J.; Shi, M.; Shoichet, M. S. Bioconjugate Chem. 2008, 20, 87
82. Nicolas, N.; Bensaid, F.; Desmaële, D.; Grogna, M.; Detrembleur, C.; Andrieux, K.; Couvreur, P. Macromolecules 2008, 41, 8418
83. Bae, J. W.; Lee, E.; Park, K. M.; Park, K. D. Macromolecules 2009, 42, 3437
84. Delaittre, G.; Justribó-Hernández, G.; Nolte, R. J. M.; Cornelissen, J. J. L. M. Macromol. Rapid Commun. 2011, 32, 19
85. Opsteen, J. A.; Brinkhuis, R. P.; Teeuwen, R. L. M.; Löwik, D. W. P. M.; van Hest, J. C. M. Chem. Commun. 2007, 3136
86. Meng, Z.; Hendrickson, G. R.; Lyon, L. A. Macromolecules 2009, 42, 7664
87. Delaittre, G.; Rieger, J.; Charleux, B. Macromolecules 2011, 44, 462 and references therein
88. Teodorescu, M.; Matyjaszewski, K. Macromolecules 1999, 32, 4826
89. Rademacher, J. T.; Baum, M.; Pallack, M. E.; Brittain, W. J.; Simonsick, W. J. Macromolecules 1999, 33, 284
90. Xia, Y.; Yin, X.; Burke, N. A. D.; Stöver, H. D. H. Macromolecules 2005, 38, 5937
91. Moad, G.; Rizzardo, E.; Thang, S. H. Aust. J. Chem. 2005, 58, 379
92. Favier, A.; Charreyre, M.-T. Macromol. Rapid Commun. 2006, 27, 653