Reactive polymer coatings: A general route to thiol-ene and thiol-yne click reactions

Macromolecular Rapid Communications

Volumn 33, Issue 10, 2012, Pages 922-927

  Wu, Jyun Ting ^a   Huang, Chi Hui ^a   Liang, Wei Chieh ^a   Wu, Yen Lin ^a   Yu, Jiashing ^a   Chen, Hsien Yeh ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

chemical vapor deposition; click chemistry; reactive polymer coatings; thiol ene coupling; thiol yne coupling

Indexed keywords

BIOLOGICAL FUNCTIONS; BULK PROPERTIES; CELL ATTACHMENTS; CLICK CHEMISTRY; CLICK REACTION; POLYMERIZATION PROCESS; PROTEIN ADSORPTION; SUBSTRATE MATERIAL; SURFACE DESIGN; SURFACE FUNCTIONS; THIOL-ENE COUPLING; THIOL-ENES;

CHEMICAL VAPOR DEPOSITION; MATERIALS PROPERTIES; POLYETHYLENE GLYCOLS; POLYMERS; VAPORS;

PLASTIC COATINGS;

ALEXA FLUOR 546; ALKENE; ALKYNE; FIBRINOGEN; POLYMER; QUINOLINE DERIVATIVE; THIOL DERIVATIVE;

AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; CLICK CHEMISTRY; GAS; POLYMERIZATION; SURFACE PROPERTY;

ALKENES; ALKYNES; AMINO ACID SEQUENCE; CLICK CHEMISTRY; FIBRINOGEN; GASES; POLYMERIZATION; POLYMERS; QUINOLINIUM COMPOUNDS; SULFHYDRYL COMPOUNDS; SURFACE PROPERTIES;

EID: 84861307062     PISSN: 10221336     EISSN: 15213927     Source Type: Journal    
DOI: 10.1002/marc.201200011     Document Type: Article

References (62)

1. D. G. Castner, Nature 2003, 422, 129.
2. B. D. Ratner, S. J. Bryant, Annu. Rev. Biomed. Eng. 2004, 6, 41.
3. C. Wöll, Angew. Chem. Int. Ed. 2009, 48, 8406.
4. A. Chilkoti, J. A. Hubbell, MRS Bull. 2005, 30, 175.
5. N. A. Kotov, J. O. Winter, I. P. Clements, E. Jan, B. P. Timko, S. Campidelli, S. Pathak, A. Mazzatenta, C. M. Lieber, M. Prato, R. V. Bellamkonda, G. A. Silva, N. W. S. Kam, F. Patolsky, L. Ballerini, Adv. Mater. 2009, 21, 3970.
6. Z. H. Nie, E. Kumacheva, Nat. Mater. 2008, 7, 277.
7. N. Patel, R. Padera, G. H. W. Sanders, S. M. Cannizzaro, M. C. Davies, R. Langer, C. J. Roberts, S. J. B. Tendler, P. M. Williams, K. M. Shakesheff, FASEB J. 1998, 12, 1447.
8. D. Falconnet, G. Csucs, H. M. Grandin, M. Textor, Biomaterials 2006, 27, 3044.
9. J. A. A. W. Elemans, S. De Feyter, Soft Matter 2009, 5, 721.
10. A. E. Nel, L. Maedler, D. Velegol, T. Xia, E. M. V. Hoek, P. Somasundaran, F. Klaessig, V. Castranova, M. Thompson, Nat. Mater. 2009, 8, 543.
11. X. Jiang, H.-Y. Chen, G. Galvan, M. Yoshida, J. Lahann, Adv. Funct. Mater. 2008, 18, 27.
12. M. Q. Zhang, T. Desai, M. Ferrari, Biomaterials 1998, 19, 953.
13. D. G. Castner, B. D. Ratner, Surf. Sci. 2002, 500, 28.
14. L. K. Keefer, Nat. Mater. 2003, 2, 357.
15. H. Nandivada, H.-Y. Chen, Y. Elkasabi, J. Lahann, in Polymers for Biomedical Applications, American Chemical Society, Washington, DC 2008, p. 283.
16. S. Morgenthaler, C. Zink, N. D. Spencer, Soft Matter 2008, 4, 419.
17. M. S. Kim, G. Khang, H. B. Lee, Prog. Polym. Sci. 2008, 33, 138.
18. T. Posner, Ber. Dtsch. Chem. Ges. 1905, 38, 646.
19. M. J. Kade, D. J. Burke, C. J. Hawker, J. Polym. Sci. Part A: Polym. Chem. 2010, 48, 743.
20. G. T. Hermanson, Bioconjugate Techniques, Academic Press, San Diego, California 1996, p. xxv.
21. J. W. Chan, H. Zhou, C. E. Hoyle, A. B. Lowe, Chem. Mater. 2009, 21, 1579.
22. C. Wendeln, S. Rinnen, C. Schulz, H. F. Arlinghaus, B. J. Ravoo, Langmuir 2010, 26, 15966.
23. R. M. Hensarling, V. A. Doughty, J. W. Chan, D. L. Patton, J. Am. Chem. Soc. 2009, 131, 14673.
24. H. Nandivada, X. Jiang, J. Lahann, Adv. Mater. 2007, 19, 2197.
25. W. H. Binder, R. Sachsenhofer, Macromol. Rapid Commun. 2007, 28, 15.
26. A. Dondoni, Angew. Chem. Int. Ed. 2008, 47, 8995.
27. C. E. Hoyle, C. N. Bowman, Angew. Chem. Int. Ed. 2010, 49, 1540.
28. L. M. Campos, K. L. Killops, R. Sakai, J. M. J. Paulusse, D. Damiron, E. Drockenmuller, B. W. Messmore, C. J. Hawker, Macromolecules 2008, 41, 7063.
29. K. L. Killops, L. M. Campos, C. J. Hawker, J. Am. Chem. Soc. 2008, 130, 5062.
30. C. Nilsson, N. Simpson, M. Malkoch, M. Johansson, E. Malmström, J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 1339.
31. R. L. A. David, J. A. Kornfield, Macromolecules 2008, 41, 1151.
32. H. Lin, X. Wan, X. Jiang, Q. Wang, J. Yin, Adv. Funct. Mater. 2011, 21, 2960.
33. K. Y. van Berkel, C. J. Hawker, J. Polym. Sci. Part A: Polym. Chem. 2010, 48, 1594.
34. M. W. Jones, G. Mantovani, S. M. Ryan, X. X. Wang, D. J. Brayden, D. M. Haddleton, Chem. Commun. 2009, 35, 5272.
35. N. Gupta, B. F. Lin, L. Campos, M. D. Dimitriou, S. T. Hikita, N. D. Treat, M. V. Tirrell, D. O. Clegg, E. J. Kramer, C. J. Hawker, Nat. Chem. 2010, 2, 138.
36. A. K. Tucker-Schwartz, R. A. Farrell, R. L. Garrell, J. Am. Chem. Soc. 2011, 133, 11026.
37. B. Yu, J. W. Chan, C. E. Hoyle, A. B. Lowe, J. Polym. Sci. Part A: Polym. Chem. 2009, 47, 3544.
38. D. Weinrich, P.-C. Lin, P. Jonkheijm, U. T. T. Nguyen, H. Schröder, C. M. Niemeyer, K. Alexandrov, R. Goody, H. Waldmann, Angew. Chem. Int. Ed. 2010, 49, 1252.
39. J.-J. Chen, K. N. Struk, A. B. Brennan, Langmuir 2011, 27, 13754.
40. A. W. Harant, V. S. Khire, M. S. Thibodaux, C. N. Bowman, Macromolecules 2006, 39, 1461.
41. J. M. Spruell, M. Wolffs, F. A. Leibfarth, B. C. Stahl, J. Heo, L. A. Connal, J. Hu, C. J. Hawker, J. Am. Chem. Soc. 2011, 133, 16698.
42. P. Tingaut, R. Hauert, T. Zimmermann, J. Mater. Chem. 2011, 21, 16066.
43. J. P. Phillips, N. M. Mackey, B. S. Confait, D. T. Heaps, X. Deng, M. L. Todd, S. Stevenson, H. Zhou, C. E. Hoyle, Chem. Mater. 2008, 20, 5240.
44. A. Kusumo, L. Bombalski, Q. Lin, K. Matyjaszewski, J. W. Schneider, R. D. Tilton, Langmuir 2007, 23, 4448.
45. H. W. Duan, M. Kuang, D. Y. Wang, D. G. Kurth, H. Mohwald, Angew. Chem. Int. Ed. 2005, 44, 1717.
46. H.-Y. Chen, J. Lahann, Langmuir 2010, 27, 34.
47. H.-Y. Chen, J.-M. Rouillard, E. Gulari, J. Lahann, Proc. Natl. Acad. Sci. USA 2007, 104, 1 1173.
48. H.-Y. Chen, J. Lahann, Adv. Mater. 2007, 19, 3801.
49. H.-Y. Chen, J. Lahann, Bioanalysis 2010, 2, 1717.
50. H.-Y. Chen, M. Hirtz, X. Deng, T. Laue, H. Fuchs, J. Lahann, J. Am. Chem. Soc. 2010, 132, 18023.
51. H.-Y. Chen, Y. Elkasabi, J. Lahann, J. Am. Chem. Soc. 2006, 128, 374.
52. J. Lahann, Polym. Int. 2006, 55, 1361.
53. J. Lahann, Chem. Eng. Commun. 2006, 193, 1457.
54. J. Lahann, R. Langer, Macromolecules 2002, 35, 4380.
55. S. Iwatsuki, T. Itoh, M. Kubo, H. Okuno, Polym. Bull. 1994, 32, 27.
56. H.-Y. Chen, J. H. Lai, X. Jiang, J. Lahann, Adv. Mater. 2008, 20, 3474.
57. H. Nandivada, H.-Y. Chen, L. Bondarenko, J. Lahann, Angew. Chem. Int. Ed. 2006, 45, 3360.
58. J. Lahann, D. Klee, W. Pluester, H. Hoecker, Biomaterials 2001, 22, 817.
59. H. Nandivada, H.-Y. Chen, J. Lahann, Macromol. Rapid Commun. 2005, 26, 1794.
60. Y. Elkasabi, H. Nandivada, H.-Y. Chen, S. Bhaskar, J. D'Arcy, L. Bondarenko, J. Lahann, Chem. Vap. Deposition 2009, 15, 142.
61. E. Wischerhoff, K. Uhlig, A. Lankenau, H. G. Börner, A. Laschewsky, C. Duschl, J.-F. Lutz, Angew. Chem. Int. Ed. 2008, 47, 5666.
62. H. Du, P. Chandaroy, S. W. Hui, Biochim. Biophys. Acta-Biomembr. 1997, 1326, 236.