Functionalization of Reactive Polymeric Coatings via Diels-Alder Reaction Using Microcontact Printing (original) (raw)

Abstract

The fabrication of polymeric thin fi lms amenable to facile functionalization by reactive μ CP via a Diels-Alder reaction is described. Precursor copolymers containing FuMA, PEGMA, and TMSMA are prepared using ATRP. Surface-tethered thin fi lms of these polymers are obtained on oxidized silicon and glass substrates and patterned with maleimide-appended dye molecules by simple μ CP to demonstrate effi cient functionalization via Diels-Alder reaction. Printing of biotin-based ligands is carried out to demonstrate directed immobilization of the enzyme streptavidin. Due to the thermoreversible nature of the Diels-Alder reaction, these surfaces can be used as rewritable platforms. This is demonstrated by sequential write-erase-rewrite protocols via μ CP of a maleimide-containing fl uorescent dye.

Loading...

Loading Preview

Sorry, preview is currently unavailable. You can download the paper by clicking the button above.

References (33)

  1. Received: July 15, 2011 ; Published online: October 12, 2011; DOI: 10.1002/macp.201100406
  2. Keywords: bioimmobilization ; click reactions; Diels-Alder polymers ; microcontact printing ; thermoreversibility Figure 5 . Reversible reactive microcontact printing on the polymer-coated surfaces.
  3. a) S. J. Park , K. B. Lee , I. S. Choi , R. Langer , S. Jon , Langmuir , 2007 , 23 , 10902 ;
  4. I. Gill , A. Ballesteros , Trends Biotechnol. 2000 , 18 , 282 .
  5. a) H. R. Rengifo , L. Chen , C. Grigoras , J. Ju , J. T. Koberstein , Langmuir , 2008 , 24 , 7450 ;
  6. L. Nebhani , C. Barner-Kowollik , Adv. Mater. 2009 , 21 , 3442 ;
  7. N. K. Devaraj , J. P. Collman , QSAR Comb. Sci. 2007 , 26 , 1253 .
  8. N. Kuramoto , K. Hayashi , K. Nacai , J. Polym. Sci., Part A: Polym. Chem. 2003 , 32 , 2501 .
  9. a) Y. Chujo , K. Sada , T. Saegusa , Macromolecules, 1990 , 23 , 2636 ;
  10. E. Goiti , M. B. Huglin , J. M. Rego , Macromol. Rapid Commun. 2003 , 24 , 692 ;
  11. S. A. Canary , M. P. Stevens , J. Polym. Sci., Part A: Polym. Chem. 1992 , 30 , 1755 .
  12. a) X. Chen , M. A. Dam , K. Ono , A. Mal , H. Shen , S. R. Nutt , K. Sheran , F. Wudl , Science 2002 , 295 , 1698 ;
  13. A. Sanyal , Macromol. Chem. Phys. 2010 , 211 , 1417 ;
  14. A. Gandini , Polym. Chem. 2010 , 1 , 245 .
  15. B. T. Houseman , M. Mrksich , Chem. Biol. 2002 , 9 , 443 ;
  16. B. T. Houseman , J. H. Huh , S. J. Kron , M. Mrksich , Nat. Biotechnol. 2002 , 20 , 270 .
  17. A. D. Araujo , J. M. Palomo , J. Cramer , M. Köhn , H. Schröder , R. Wacker , C. Niemeyer , K. Alexandrov , H. Waldmann , Angew. Chem. Int. Ed. 2006 , 45 , 296 .
  18. A. S. Goldmann , T. Tischer , L. Barner , M. Bruns , C. Barner-Kowollik , Biomacromolecules 2011 , 12 , 1137 .
  19. A. Kumar , H. A. Biebuyck , G. M. Whitesides , Langmuir 1994 , 10 , 1498 .
  20. E. Wischerhoff , K. Uhlig , A. Lankenau , H. G. Börner , A. Laschewsky , C. Duschl , J. F. Lutz , Angew. Chem. Int. Ed. 2008 , 47 , 5666 .
  21. K. Uhlig , E. Wischerhoff , J. F. Lutz , A. Laschewsky , M. S. Jaeger , A. Lankenau , C. Duschl , Soft Matter 2010 , 6 , 4262 .
  22. J. L. Shepherd , A. Kell , E. Chung , C. W. Sinclar , M. S. Workentin , D. Bizzotto , J. Am. Chem. Soc. 2004 , 126 , 8329 .
  23. A. A. Kavitha , N. K. Singha , Macromol. Chem. Phys. 2007 , 208 , 2569 ;
  24. H. Dutta , A. K. Bhowmick , N. K. Singha , J. Polym. Sci., Part A: Polym. Chem. 2007 , 45 , 1661 ;
  25. A. A. Kavitha , N. K. Singha , ACS Appl. Mater. Interfaces 2009 , 1 , 1427 .
  26. B. J. Ravoo , J. Mater. Chem. 2009 , 19 , 8902 .
  27. C. Wendeln , A. Heile , H. F. Arlinghaus , B. J. Ravoo , Langmuir 2010 , 26 , 4933 .
  28. J. Mehlich , B. J. Ravoo , Org. Biomol. Chem. 2011 , 9 , 4108 .
  29. A. Kikuchi , T. Okano , Adv. Drug Delivery Rev. 2002 , 54 , 53 ;
  30. J. C. Cuggino , M. C. Strumia , C. I. A. Igarzabal , React. Funct. Polym. 2011 , 71 , 440 .
  31. W. C. E. Schofi eld , J. McGettrick , T. J. Bradley , J. P. S. Badyal , S. Przyborski , J. Am. Chem. Soc. 2006 , 128 , 2280 .
  32. L. G. Harris , W. C. E. Schofi eld , K. J. Doores , B. G. Davis , J. P. S. Badyal , J. Am. Chem. Soc. 2009 , 131 , 7755 .
  33. F. Zhang , E. T. Kang , K. G. Neoh , W. Huang , J. Biomater. Sci. Polym Ed. 2001 , 12 , 515 .