Spatial and temporal control of thiol-michael addition via photocaged superbase in photopatterning and two-stage polymer networks formation

Macromolecules

Volumn 47, Issue 18, 2014, Pages 6159-6165

  Xi, Weixian ^a   Peng, Haiyan ^a,b   Aguirre Soto, Alan ^a   Kloxin, Christopher J ^c   Stansbury, Jeffery W ^a   Bowman, Christopher N ^a  

^a UCB 450   (United States)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^c UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; POLYMERS;

EXTERNAL CONTROL; MICHAEL ADDITIONS; PHOTO PATTERNING; PHOTOCHEMICAL PROCESS; POLYMER NETWORKS; POLYMER SYNTHESIS; SURFACE PATTERNING; TEMPORAL CONTROLS;

PHOTOCHEMICAL REACTIONS;

EID: 84918546787     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/ma501366f     Document Type: Article

References (51)

1. Kolb, H. C; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.
2. (a) Golas, P. L.; Matyjaszewski, K. Chem. Soc. Rev. 2010, 39, 1338.
3. (b) Iha, R. K.; Wooley, K. L.; Nystrom, A. M.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Chem. Rev. 2009, 109, 5620.
4. (c) Xi, W.; Scott, T. F.; Kloxin, C. J.; Bowman, C. N. Adv. Funct. Mater. 2014, 24, 2572.
5. (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
6. (b) Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
7. (a) Lowe, A. B. Polym. Chem. 2010, 1, 17.
8. (b) Hoyle, C. E.; Bowman, C. N. Angew. Chem., Int. Ed. 2010, 49, 1540.
9. Nair, D. P.; Podgorski, M.; Chatani, S.; Gong, T.; Xi, W. X.; Fenoli, C. R.; Bowman, C. N. Chem. Mater. 2014, 26, 724.
10. Li, H. B.; Yu, B.; Matsushima, H.; Hoyle, C. E.; Lowe, A. B. Macromolecules 2009, 42, 6537.
11. Tasdelen, M. A.; Yagci, Y. Angew. Chem., Int. Ed. 2013, 52, 5930.
12. (a) Tasdelen, M. A.; Yagci, Y. Tetrahedron lett. 2010, 51, 6945.
13. (b) Adzima, B. J.; Tao, Y.; Kloxin, C. J.; DeForest, C. A.; Anseth, K. S.; Bowman, C. N. Nat. Chem. 2011, 3, 256.
14. Poloukhtine, A. A.; Mbua, N. E.; Wolfert, M. A.; Boons, G. J.; Popik, V. V. J. Am. Chem. Soc. 2009, 131, 15769.
15. (a) Wang, Y. Z.; Song, W. J.; Hu, W. J.; Lin, Q. Angew. Chem., Int. Ed. 2009, 48, 5330.
16. (b) Song, W.; Wang, Y.; Qu, J.; Lin, Q. J. Am. Chem. Soc. 2008, 130, 9654.
17. (c) Song, W.; Wang, Y.; Qu, J.; Madden, M. M.; Lin, Q. Angew. Chem., Int. Ed. 2008, 47, 2832.
18. (a) Arumugam, S.; Popik, V. V. J. Am. Chem. Soc. 2012, 134, 8408.
19. (b) Arumugam, S.; Orski, S. V.; Locklin, J.; Popik, V. V. J. Am. Chem. Soc. 2012, 134, 179.
20. (c) Arumugam, S.; Popik, V. V. J. Am. Chem. Soc. 2011, 133, 15730.
21. Pauloehrl, T.; Delaittre, G.; Bruns, M.; Meissler, M.; Borner, H. G.; Bastmeyer, M.; Barner-Kowollik, C. Angew. Chem., Int. Ed. 2012, 51, 9181.
22. (a) Blasco, E.; Pinol, M.; Oriol, L.; Schmidt, B. V. K. J.; Welle, A.; Trouillet, V.; Bruns, M.; Barner-Kowollik, C. Adv. Funct. Mater. 2013, 23, 4011.
23. (b) Rodriguez-Emmenegger, C.; Preuss, C. M.; Yameen, B.; Pop-Georgievski, O.; Bachmann, M.; Mueller, J. O.; Bruns, M.; Goldmann, A. S.; Bastmeyer, M.; Barner-Kowollik, C. Adv. Mater. 2013, 25, 6123.
24. (c) Dietrich, M.; Delaittre, G.; Blinco, J. P.; Inglis, A. J.; Bruns, M.; Barner-Kowollik, C. Adv. Funct. Mater. 2012, 22, 304.
25. (d) Gupta, N.; Lin, B. F.; Campos, L.; Dimitriou, M. D.; Hikita, S. T.; Treat, N. D.; Tirrell, M. V.; Clegg, D. O.; Kramer, E. J.; Hawker, C. J. Nat. Chem. 2010, 2, 138.
26. (e) Kloxin, C. J.; Scott, T. F.; Park, H. Y.; Bowman, C. N. Adv. Mater. 2011, 23, 1977.
27. (a) Gruendling, T.; Oehlenschlaeger, K. K.; Frick, E.; Glassner, M.; Schmid, C.; Barner-Kowollik, C. Macromol. Rapid Commun. 2011, 32, 807.
28. (b) Oehlenschlaeger, K. K.; Mueller, J. O.; Heine, N. B.; Glassner, M.; Guimard, N. K.; Delaittre, G.; Schmidt, F. G.; Barner-Kowollik, C. Angew. Chem., Int. Ed. 2013, 52, 762.
29. (a) Valkevich, E. M.; Guenette, R. G.; Sanchez, N. A.; Chen, Y. C.; Ge, Y.; Strieter, E. R. J. Am. Chem. Soc. 2012, 134, 6916.
30. (b) Bauer, D. M.; Rogge, A.; Stolzer, L.; Barner-Kowollik, C.; Fruk, L. Chem. Commun. 2013, 49, 8626.
31. (a) Pauloehrl, T.; Welle, A.; Bruns, M.; Linkert, K.; Borner, H. G.; Bastmeyer, M.; Delaittre, G.; Barner-Kowollik, C. Angew. Chem., Int. Ed. 2013, 52, 9714.
32. (b) Pauloehrl, T.; Welle, A.; Oehlenschlaeger, K. K.; Barner-Kowollik, C. Chem. Sci. 2013, 4, 3503.
33. (c) Tischer, T.; Claus, T. K.; Bruns, M.; Trouillet, V.; Linkert, K.; Rodriguez-Emmenegger, C.; Goldmann, A. S.; Perrier, S.; Borner, H. G.; Barner-Kowollik, C. Biomacromolecules 2013, 14, 4340.
34. (d) Pauloehrl, T.; Delaittre, G.; Winkler, V.; Welle, A.; Bruns, M.; Borner, H. G.; Greiner, A. M.; Bastmeyer, M.; Barner-Kowollik, C. Angew. Chem., Int. Ed. 2012, 51, 1071.
35. (a) Tucker-Schwartz, A. K.; Farrell, R. A.; Garrell, R. L. J. Am. Chem. Soc. 2011, 133, 11026.
36. (b) Altintas, O.; Willenbacher, J.; Wuest, K. N. R.; Oehlenschlaeger, K. K.; Krolla-Sidenstein, P.; Gliemann, H.; Barner-Kowollik, C. Macromolecules 2013, 46, 8092.
37. (c) Stolzer, L.; Ahmed, I.; Rodriguez-Emmenegger, C.; Trouillet, V.; Bockstaller, P.; Barner-Kowollik, C.; Fruk, L. Chem. Commun. 2014, 50, 4430.
38. (a) Ning, X. H.; Guo, J.; Wolfert, M. A.; Boons, G. J. Angew. Chem., Int. Ed. 2008, 47, 2253.
39. (b) Shafiq, Z.; Cui, J. X.; Pastor-Perez, L.; San Miguel, V.; Gropeanu, R. A.; Serrano, C.; del Campo, A. Angew. Chem., Int. Ed. 2012, 51, 4332.
40. Gong, T.; Adzima, B. J.; Baker, N. H.; Bowman, C. N. Adv. Mater. 2013, 25, 2024.
41. (a) Chan, J. W.; Hoyle, C. E.; Lowe, A. B.; Bowman, M. Macromolecules 2010, 43, 6381.
42. (b) Xi, W.; Wang, C.; Kloxin, C. J.; Bowman, C. N. ACS Macro Lett. 2012, 1, 811.
43. (a) Dietliker, K.; Husler, R.; Birbaum, J. L.; Ilg, S.; Villeneuve, S.; Studer, K.; Jung, T.; Benkhoff, J.; Kura, H.; Matsumoto, A.; Oka, H. Prog. Org. Coat. 2007, 58, 146.
44. (b) Liang, Y. K.; Kiick, K. L. Polym. Chem. 2014, 5, 1728.
45. Stoll, R. S.; Hecht, S. Angew. Chem., Int. Ed. 2010, 49, 5054.
46. Xi, W.; Krieger, M.; Kloxin, C. J.; Bowman, C. N. Chem. Commun. 2013, 49, 4504.
47. (a) Ishikawa, T.; Kumamoto, T. Synthesis 2006, 5, 737.
48. (b) Bochet, C. G. J. Chem. Soc., Perkin Trans. 1 2002, 1, 125.
49. Hasan, A.; Stengele, K. P.; Giegrich, H.; Cornwell, P.; Isham, K. R.; Sachleben, R. A.; Pfleiderer, W.; Foote, R. S. Tetrahedron 1997, 53, 4247.
50. Cramer, N. B.; Bowman, C. N. J. Polym. Sci., Polym. Chem. 2001, 39, 3311.
51. Li, G. Z.; Randev, R. K.; Soeriyadi, A. H.; Rees, G.; Boyer, C.; Tong, Z.; Davis, T. P.; Becer, C. R.; Haddleton, D. M. Polym. Chem. 2010, 1, 1196.