Photoclickable surfaces for profluorescent covalent polymer coatings

Advanced Functional Materials

Volumn 22, Issue 2, 2012, Pages 304-312

  Dietrich, Mathias ^a,b   Delaittre, Guillaume ^a   Blinco, James P ^a   Inglis, Andrew J ^a   Bruns, Michael ^c   Barner Kowollik, Christopher ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^b FRAUNHOFER INSTITUTE FOR CHEMICAL TECHNOLOGY ICT   (Germany)

^c KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

cellulose; grafting; photochemistry; surface patterning; X ray photoelectron spectroscopy

Indexed keywords

1 ,3-DIPOLARCYCLOADDITION; AMIDIFICATION; CYCLOADDITION REACTION; OPTIMIZED REACTION CONDITIONS; PHOTO-INDUCED; POLYMER CHAINS; POLYMER COATING; SILANIZATIONS; SURFACE CHARACTERIZATION; SURFACE PATTERNING; UV IRRADIATION;

BLOCK COPOLYMERS; CELLULOSE; CYANIDES; CYCLOADDITION; FLUORESCENCE; GRAFTING (CHEMICAL); IRRADIATION; MACROMOLECULES; OLEFINS; PHOTOCHEMICAL REACTIONS; PHOTONS; SILICON COMPOUNDS; SILICON OXIDES; X RAY PHOTOELECTRON SPECTROSCOPY;

FUNCTIONAL POLYMERS;

EID: 84856108064     PISSN: 1616301X     EISSN: 16163028     Source Type: Journal    
DOI: 10.1002/adfm.201102068     Document Type: Article

References (75)

1. Polymer Brushes: Synthesis, Characterization, Applications (Eds:, R. C. Advincula, W. J. Brittain, K. C. Caster, J. Rühe,), Wiley-VCH, Weinheim, Germany 2004.
2. B. Zhao, W. J. Brittain, Prog. Polym. Sci. 2000, 25, 677.
3. L. Nebhani, D. Schmiedl, L. Barner, C. Barner-Kowollik, Adv. Funct. Mater. 2010, 20, 2010.
4. a) W. A. Braunecker, K. Matyjaszewski, Prog. Polym. Sci. 2007, 32, 93
5. b) A. D. Jenkins, R. G. Jones, G. Moad, Pure Appl. Chem. 2010, 82, 483.
6. a) D. H. Solomon, E. Rizzardo, P. Cacioli,; EP135280 1985
7. b) D. H. Solomon, E. Rizzardo, P. Cacioli, Chem. Abstr. 1985, 102, 221335q
8. c) C. J. Hawker, A. W. Bosman, E. Harth, Chem. Rev. 2001, 101, 3661.
9. a) M. Kamigaito, T. Ando, M. Sawamoto, Chem. Rev. 2001, 101, 3689
10. b) K. Matyjaszewski, J. Xia, Chem. Rev. 2001, 101, 2921.
11. a) Handbook of RAFT Polymerization (Ed:, C. Barner-Kowollik,), Wiley-VCH, Weinheim, Germany 2008
12. b) G. Moad, E. Rizzardo, S. H. Tang, Aust. J. Chem. 2005, 58, 379
13. c) G. Moad, E. Rizzardo, S. H. Tang, Aust. J. Chem. 2006, 59, 669
14. d) G. Moad, E. Rizzardo, S. H. Tang, Aust. J. Chem. 2009, 62, 1402.
15. a) H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. Int. Ed. 2001, 40, 2004
16. b) C. Barner-Kowollik, F. E. Du Prez, P. Espeel, C. J. Hawker, T. Junkers, H. Schlaad, W. Van Camp, Angew. Chem. Int. Ed. 2011, 50, 60.
17. a) C. J. Hawker, K. L. Wooley, Science 2005, 309, 1200
18. b) W. H. Binder, R. Sachsenhofer, Macromol. Rapid Commun. 2007, 28, 15
19. c) C. Barner-Kowollik, A. J. Inglis, Macromol. Chem. Phys. 2009, 210, 987
20. d) R. K. Iha, K. L. Wooley, A. N. Nystrom, D. J. Burke, M. J. Kade, C. J. Hawker, Chem. Rev. 2009, 109, 5620
21. e) P. L. Golas, K. Matyjaszewski, Chem. Soc. Rev. 2010, 39, 1338.
22. a) R. A. Evans, Aus. J. Chem. 2007, 60, 384
23. b) S. Sinnwell, A. J. Inglis, M. H. Stenzel, C. Barner-Kowollik, in Click Chemistry for Biotechnology and Materials Science (Ed:, J. Lahann,), Wiley, Chichester, UK 2009, Ch. 6
24. c) H. Nandivada, J. Lahann, in Click Chemistry for Biotechnology and Materials Science (Ed:, J. Lahann,), Wiley, Chichester, UK 2009, Ch. 12
25. d) A. J. Inglis, C. Barner-Kowollik, Macromol. Rapid Commun. 2010, 31, 1247
26. e) U. Mansfeld, C. Pietsch, R. Hoogenboom, C. R. Becer, U. S. Schubert, Polym. Chem. 2010, 1, 1560.
27. a) S. Luza, H. Speisky, Am. J. Clin. Nutr. 1996, 63, 812S
28. b) F. Wolbers, P. ter Braak, S. Le Gac, R. Luttge, H. Andersson, I. Vermes, A. van den Berg, Electrophoresis 2006, 27, 5073
29. c) E. M. Sletten, C. R. Bertozzi, Angew. Chem. Int. Ed. 2009, 48, 6974.
30. a) C. R. Becer, R. Hoogenboom, U. S. Schubert, Angew. Chem. Int. Ed. 2009, 48, 4900
31. b) J. T. Kopping, Z. P. Tolstyka, H. D. Maynard, Macromolecules 2007, 40, 8593
32. c) A. J. Inglis, S. Sinnwell, M. H. Stenzel, C. Barner-Kowollik, Angew. Chem. Int. Ed. 2009, 48, 2411
33. d) C. Ott, R. Hoogenboom, U. S. Schubert, Chem. Commun. 2008, 3516
34. e) I. Singh, Z. Zarafshani, J.-F. Lutz, F. Heaney, Macromolecules 2009, 42, 5411
35. f) J. Moraes, T. Maschmeyer, S. Perrier, J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 2771
36. g) C. F. Hansell, P. Espeel, M. M. Stamenovic, I. A. Barker, A. P. Dove, F. E. Du Prez, R. K. O'Reilly, J. Am. Chem. Soc. 2011, 133, 13828
37. h) M. Conradi, T. Junkers, Macromolecules 2011, 44, 7969.
38. a) C. E. Hoyle, C. N. Bowman, Angew. Chem. Int. Ed. 2010, 49, 1540
39. b) R. Hoogenboom, Angew. Chem. Int. Ed. 2010, 49, 3415
40. c) C. E. Hoyle, A. B. Lowe, C. N. Bowman, Chem. Soc. Rev. 2010, 39, 1355.
41. a) T. Gruendling, K. K. Oehlenschlaeger, E. Frick, M. Glassner, C. Schmid, C. Barner-Kowollik, Macromol. Rapid Commun. 2011, 32, 807
42. b) M. Glassner, K. K. Oehlenschlaeger, T. Gruendling, C. Barner-Kowollik, Macromolecules 2011, 44, 4681.
43. a) Y. Wang, C. I. Rivera Vera, Q. Lin, Org. Lett. 2007, 9, 4155
44. b) Y. Wang, W. J. Hu, W. Song, R. K. V. Lim, Q. Lin, Org. Lett. 2008, 10, 3725
45. c) W. Song, Y. Wang, J. Qu, M. M. Madden, Q. Lin, Angew. Chem. Int. Ed. 2008, 47, 2832.
46. J. S. Clovis, A. Eckell, R. Huisgen, R. Sustmann, Chem. Ber. 1967, 100, 60.
47. a) H. Meier, H. Heimgartner, Helv. Chim. Acta 1985, 68, 1283
48. b) V. Lohse, P. Leihkauf, C. Csongar, G. Tomaschewski, J. Prakt. Chem. 1988, 330, 406
49. c) R. Darkow, M. Yoshikawa, T. Kitao, G. Tomaschewski, J. Schellenberg, J. Polym. Sci., Part A: Polym. Chem. 1994, 32, 1657.
50. a) G. Bertrand, C. Wentrup, Angew. Chem. Int. Ed. 1994, 33, 527
51. b) D. Moderhack, J. Prakt. Chem. 1998, 340, 687.
52. J. Wang, W. Zhang, W. Song, Y. Wang, Z. Yu, J. Li, M. Wu, L. Wang, J. Zang, Q. Lin, J. Am. Chem. Soc. 2010, 132, 14812.
53. a) W. Song, Y. Wang, J. Qu, Q. Lin, J. Am. Chem. Soc. 2008, 130, 9654
54. b) Y. Wang, W. Song, W. Hu, Q. Lin, Angew. Chem. Int. Ed. 2009, 48, 5330.
55. M. M. Madden, C. I. Rivera Vera, W. Song, Q. Lin, Chem. Commun. 2009, 5588.
56. a) Z. Yu, R. K. V. Lim, Q. Lin, Chem.-Eur. J. 2010, 16, 13325
57. b) R. K. V. Lim, Q. Lin, Acc. Chem. Res. 2011, in press, DOI: 10.1021/ar200021p
58. c) Z. Yu, L. Y. Ho, Z. Wang, Q. Lin, Bioorg. Med. Chem. Lett. 2011, 21, 5033.
59. G. Mantovani, F. Lecolley, L. Tao, D. M. Haddleton, J. Clerx, J. J. L. M. Cornelissen, K. Velonia, J. Am. Chem. Soc. 2005, 127, 2966.
60. A. Wagner, C.-W. Schellhammer, S. Petersen, Angew. Chem. 1966, 5, 699.
61. E. H. Lock, D. Y. Petrovykh, P. Mack, T. Carney, R. G. White, S. G. Walton, R. F. Fernsler, Langmuir 2010, 26, 8857.
62. C. De Marco, S. M. Eaton, R. Suriano, S. Turri, M. Levi, R. Ramponi, G. Cerullo, R. Osellame, ACS Appl. Mater. Interfaces 2010, 2, 2377.
63. E. Szocs, I. Bakõ, T. Kosztolányi, I. Bertõti, E. Kálmán, Electrochim. Acta 2004, 49, 1371.
64. P. G. Rouxhet, A. M. Misselyn-Bauduin, F. Ahimou, M. J. Genet, Y. Adriaensen, T. Desille, P. Bodson, C. Deroanne, Surf. Interface Anal. 2008, 40, 718.
65. a) H. Meier, W. Heinzelmann, H. Heimgartner, Chimia 1980, 34, 506
66. b) S.-L. Zheng, Y. Wang, Z. Yu, Q. Lin, P. Coppens, J. Am. Chem. Soc. 2009, 131, 18036.
67. D. Léonard, Y. Chevolot, O. Bucher, H. Sigrist, H. J. Mathieu, Surf. Interface Anal. 1998, 26, 783.
68. D. Klemm, B. Heublein, H.-P. Fink, A. Bohn, Angew. Chem. Int. Ed. 2005, 44, 3358.
69. J. S. Stevens, S. L. M. Schroeder, Surf. Interface Anal. 2009, 41, 453.
70. A. S. Goldmann, T. Tischer, L. Barner, M. Bruns, C. Barner-Kowollik, Biomacromolecules 2011, 12, 1137.
71. H. Murata, R. R. Koepsel, K. Matyjaszewski, A. J. Russell, Biomaterials 2007, 28, 4870.
72. H. A. Krässig, in Cellulose and Its Derivatives: Chemistry, Biochemistry and Applications (Eds:, J. F. Kennedy, G. O. Phillips, D. J. Wedlock, P. A. Williams,), Ellis Horwood, Ltd., Chichester, UK 1985, Ch. 1.
73. K. L. Parry, A. G. Shard, R. D. Short, R. G. White, J. D. Whittle, A. Wright, Surf. Interface Anal. 2006, 38, 1497.
74. J. H. Scofield, J. Electron Spectrosc. Relat. Phenom. 1976, 8, 129.
75. S. Tanuma, C. J. Powell, D. R. Penn, Surf. Interface Anal. 1994, 21, 165.