Self-sorting click reactions that generate spatially controlled chemical functionality on surfaces

Langmuir

Volumn 29, Issue 19, 2013, Pages 5920-5926

  Arnold, Rachelle M ^a   Locklin, Jason ^a  

^a University of Georgia   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL FUNCTIONALITY; CROSS CONTAMINATION; FUNCTIONALIZATIONS; PATTERNED SURFACE; PENTAFLUOROPHENYL; POST-POLYMERIZATION; SILICON SURFACES; TERMINAL ALKYNE;

CONDENSED MATTER PHYSICS; ELECTROCHEMISTRY;

FLUORESCENCE MICROSCOPY;

POLYMER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CLICK CHEMISTRY; FLUORESCENCE MICROSCOPY; PARTICLE SIZE; POLYMERIZATION; SURFACE PROPERTY; SYNTHESIS;

CLICK CHEMISTRY; MICROSCOPY, FLUORESCENCE; MOLECULAR STRUCTURE; PARTICLE SIZE; POLYMERIZATION; POLYMERS; SURFACE PROPERTIES;

EID: 84877724390     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la4012857     Document Type: Article

References (61)

1. Burd, C.; Weck, M. Self-sorting in polymers Macromolecules 2005, 38, 7225-7230
2. Mukhopadhyay, P.; Wu, A.; Isaacs, L. Social self-sorting in aqueous solution J. Org. Chem. 2004, 69, 6157-6164
3. Safont-Sempere, M. M.; Fernández, G.; Würthner, F. Self-sorting phenomena in complex supramolecular systems Chem. Rev. 2011, 111, 5784-5814
4. Wu, A.; Isaacs, L. Self-sorting: The exception or the rule? J. Am. Chem. Soc. 2003, 125, 4831-4835
5. Lehn, J.-M. Toward self-organization and complex matter Science 2002, 295, 2400-2403
6. Bilgiçer, B.; Xing, X.; Kumar, K. Programmed self-sorting of coiled coils with leucine and hexafluoroleucine cores J. Am. Chem. Soc. 2001, 123, 11815-11816
7. Schnarr, N. A.; Kennan, A. J. Specific control of peptide assembly with combined hydrophilic and hydrophobic interfaces J. Am. Chem. Soc. 2002, 125, 667-671
8. Enemark, E. J.; Stack, T. D. P. Stereospecificity and self-selectivity in the generation of a chiral molecular tetrahedron by metal-assisted self-assembly Angew. Chem., Int. Ed. 1998, 37, 932-935
9. Kondo, T.; Oyama, K.-i.; Yoshida, K. Chiral molecular recognition on formation of a metalloanthocyanin: A supramolecular metal complex pigment from blue flowers of salvia patens Angew. Chem., Int. Ed. 2001, 40, 894-897
10. Rowan, S. J.; Hamilton, D. G.; Brady, P. A.; Sanders, J. K. M. Automated recognition, sorting, and covalent self-assembly by predisposed building blocks in a mixture J. Am. Chem. Soc. 1997, 119, 2578-2579
11. Wu, A.; Chakraborty, A.; Fettinger, J. C.; Flowers, R. A., II; Isaacs, L. Molecular clips that undergo heterochiral aggregation and self-sorting Angew. Chem., Int. Ed. 2002, 41, 4028-4031
12. Ma, Y.; Kolotuchin, S. V.; Zimmerman, S. C. Supramolecular polymer chemistry: Self-assembling dendrimers using the DDA·AAD (GC-like) hydrogen bonding motif J. Am. Chem. Soc. 2002, 124, 13757-13769
13. Gardner, T. J.; Frisbie, C. D.; Wrighton, M. S. Systems for orthogonal self-assembly of electroactive monolayers on Au and ITO: an approach to molecular electronics J. Am. Chem. Soc. 1995, 117, 6927-6933
14. Hickman, J. J.; Laibinis, P. E.; Auerbach, D. I.; Zou, C.; Gardner, T. J.; Whitesides, G. M.; Wrighton, M. S. Toward orthogonal self-assembly of redox active molecules on platinum and gold: selective reaction of disulfide with gold and isocyanide with platinum Langmuir 1992, 8, 357-359
15. Laibinis, P. E.; Hickman, J. J.; Wrighton, M. S.; Whitesides, G. M. Orthogonal self-assembled monolayers: Alkanethiols on gold and alkane carboxylic acids on alumina Science 1989, 245, 845-847
16. Farhan, T.; Huck, W. T. S. Synthesis of patterned polymer brushes from flexible polymeric films Eur. Polym. J. 2004, 40, 1599-1604
17. Konradi, R.; Rühe, J. Fabrication of chemically microstructured polymer brushes Langmuir 2006, 22, 8571-8575
18. Zhao, B.; Brittain, W. J. Polymer brushes: surface-immobilized macromolecules Prog. Polym. Sci. 2000, 25, 677-710
19. Arnold, R. M.; Huddleston, N. E.; Locklin, J. Utilizing click chemistry to design functional interfaces through post-polymerization modification J. Mater. Chem. 2012, 22, 19357-19365
20. Galvin, C. J.; Genzer, J. Applications of surface-grafted macromolecules derived from post-polymerization modification reactions Prog. Polym. Sci. 2012, 37, 871-906
21. Gauthier, M. A.; Gibson, M. I.; Klok, H.-A. Synthesis of functional polymers by post-polymerization modification Angew. Chem., Int. Ed. 2009, 48, 48-58
22. Spruell, J. M.; Wolffs, M.; Leibfarth, F. A.; Stahl, B. C.; Heo, J.; Connal, L. A.; Hu, J.; Hawker, C. J. Reactive, multifunctional polymer films through thermal cross-linking of orthogonal click groups J. Am. Chem. Soc. 2011, 133, 16698-16706
23. Im, S. G.; Bong, K. W.; Kim, B.-S.; Baxamusa, S. H.; Hammond, P. T.; Doyle, P. S.; Gleason, K. K. Patterning nanodomains with orthogonal functionalities: Solventless synthesis of self-sorting surfaces J. Am. Chem. Soc. 2008, 130, 14424-14425
24. Xu, H.; Hong, R.; Lu, T.; Uzun, O.; Rotello, V. M. Recognition-directed orthogonal self-assembly of polymers and nanoparticles on patterned surfaces J. Am. Chem. Soc. 2006, 128, 3162-3163
25. Meng, X.; Lu, Y.; Yang, B.; Yi, G.; Jia, J. Fabrication and photoelectrochemical characteristics of the patterned CdS microarrays on indium tin oxide substrates ACS Appl. Mater. Interfaces 2010, 2, 3467-3472
26. Dunderdale, G.; Howse, J.; Fairclough, P. pH-Dependent control of particle motion through surface interactions with patterned polymer brush surfaces Langmuir 2012, 28, 12955-12961
27. Liu, G.; Detcheverry, F.; Ramírez-Hernández, A.; Yoshida, H.; Tada, Y.; de Pablo, J. J.; Nealey, P. F. Nonbulk complex structures in thin films of symmetric block copolymers on chemically nanopatterned surfaces Macromolecules 2012, 45, 3986-3992
28. Chiang, E. N.; Dong, R.; Ober, C. K.; Baird, B. A. Cellular responses to patterned poly(acrylic acid) brushes Langmuir 2011, 27, 7016-7023
29. Henley, W. H.; Dennis, P. J.; Ramsey, J. M. Fabrication of microfluidic devices containing patterned microwell arrays Anal. Chem. 2011, 84, 1776-1780
30. Gates, B. D.; Xu, Q.; Stewart, M.; Ryan, D.; Willson, C. G.; Whitesides, G. M. New approaches to nanofabrication: Molding, printing, and other techniques Chem. Rev. 2005, 105, 1171-1196
31. Geissler, M.; Xia, Y. Patterning: Principles and some new developments Adv. Mater. 2004, 16, 1249-1269
32. Barbey, R.; Lavanant, L.; Paripovic, D.; Schuwer, N.; Sugnaux, C.; Tugulu, S.; Klok, H. A. Polymer brushes via surface-initiated controlled radical polymerization: synthesis, characterization, properties, and applications Chem. Rev. 2009, 109, 5437-5527
33. Katz, J. S.; Doh, J.; Irvine, D. J. Composition-tunable properties of amphiphilic comb copolymers containing protected methacrylic acid groups for multicomponent protein patterning Langmuir 2005, 22, 353-359
34. Sorribas, H.; Padeste, C.; Tiefenauer, L. Photolithographic generation of protein micropatterns for neuron culture applications Biomaterials 2002, 23, 893-900
35. Orth, R. N.; Clark, T. G.; Craighead, H. G. Avidin-biotin micropatterning methods for biosensor applications Biomed. Microdevices 2003, 5, 29-34
36. Eberhardt, M.; Mruk, R.; Zentel, R.; Théato, P. Synthesis of pentafluorophenyl(meth)acrylate polymers: New precursor polymers for the synthesis of multifunctional materials Eur. Polym. J. 2005, 41, 1569-1575
37. Malkoch, M.; Thibault, R. J.; Drockenmuller, E.; Messerschmidt, M.; Voit, B.; Russell, T. P.; Hawker, C. J. Orthogonal approaches to the simultaneous and cascade functionalization of macromolecules using click chemistry J. Am. Chem. Soc. 2005, 127, 14942-14949
38. Salic, A.; Mitchison, T. J. A chemical method for fast and sensitive detection of DNA synthesis in vivo Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 2415-2420
39. Arnold, R. M.; Sheppard, G. R.; Locklin, J. Comparative aminolysis kinetics of different active ester polymer brush platforms in postpolymerization modification with primary and aromatic amines Macromolecules 2012, 45, 5444-5450
40. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click chemistry: Diverse chemical function from a few good reactions Angew. Chem., Int. Ed. 2001, 40, 2004-2021
41. Ayres, N. Polymer brushes: Applications in biomaterials and nanotechnology Polym. Chem. 2010, 1, 769-777
42. Habicht, J.; Schmidt, M.; Rühe, J.; Johannsmann, D. Swelling of thick polymer brushes investigated with ellipsometry Langmuir 1999, 15, 2460-2465
43. Odian, G. Principles of Polymerization; John Wiley & Sons, Inc.: Hoboken, NJ, 2004.
44. Valverde, I. E.; Delmas, A. F.; Aucagne, V. Click àla carte: robust semi-orthogonal alkyne protecting groups for multiple successive azide/alkyne cycloadditions Tetrahedron 2009, 65, 7597-7602
45. Cooper, B. M.; Emrick, T. Sequential and localized grafting on aliphatic polyester diblock copolymers using alkyne deprotection and click cycloaddition J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 7054-7065
46. Friscourt, F.; Boons, G.-J. One-pot three-step synthesis of 1,2,3-triazoles by copper-catalyzed cycloaddition of azides with alkynes formed by a Sonogashira cross-coupling and desilylation Org. Lett. 2010, 12, 4936-4939
47. Hasneen, A.; Han, H. S.; Paik, H.-J. Synthesis of linear tetrablock quaterpolymers via atom transfer radical polymerization and a click coupling approach React. Funct. Polym. 2009, 69, 681-687
48. Hensarling, R. M.; Doughty, V. A.; Chan, J. W.; Patton, D. L. Clicking polymer brushes with thiol-yne chemistry: Indoors and out J. Am. Chem. Soc. 2009, 131, 14673-14675
49. Bain, E. D.; Dawes, K.; Özçam, A. E.; Hu, X.; Gorman, C. B.; Šrogl, J.; Genzer, J. Surface-initiated polymerization by means of novel, stable, non-ester-based radical initiator Macromolecules 2012, 45, 3802-3815
50. Aucagne, V.; Leigh, D. A. Chemoselective formation of successive triazole linkages in one pot: "click-click" chemistry Org. Lett. 2006, 8, 4505-4507
51. Vitérisi, A.; Orsini, A.; Weibel, J.-M.; Pale, P. A mild access to silver acetylides from trimethylsilyl acetylenes Tetrahedron Lett. 2006, 47, 2779-2781
52. Cuevas, F.; Oliva, A. I.; Pericàs, M. A. Direct copper(I)-catalyzed cycloaddition of organic azides with TMS-protected alkynes Synlett 2010, 2010, 1873-1877
53. Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates J. Am. Chem. Soc. 2004, 127, 210-216
54. Meldal, M.; Tornøe, C. W. Cu-catalyzed azide-alkyne cycloaddition Chem. Rev. 2008, 108, 2952-3015
55. Nolte, C.; Mayer, P.; Straub, B. F. Isolation of a copper(I) triazolide: A "click" intermediate Angew. Chem., Int. Ed. 2007, 46, 2101-2103
56. Murata, H.; Prucker, O.; Rühe, J. Synthesis of functionalized polymer monolayers from active ester brushes Macromolecules 2007, 40, 5497-5503
57. Ulman, A. Formation and structure of self-assembled monolayers Chem. Rev. 1996, 96, 1533-1554
58. Orski, S. V.; Fries, K. H.; Sheppard, G. R.; Locklin, J. High density scaffolding of functional polymer brushes: Surface initiated atom transfer radical polymerization of active esters Langmuir 2009, 26, 2136-2143
59. Schuh, C.; Rühe, J. Penetration of polymer brushes by chemical nonidentical free polymers Macromolecules 2011, 44, 3502-3510
60. Pearce, E. M. In Properties of Polymers, Their Estimation and Correlation with Chemical Structure, 2 nd rev. ed.; Van Krevelen, D. W., Ed.; Elsevier: Amsterdam/Oxford/New York, 1976, 620 pp.
61. J. Polym. Sci., Part B: Polym. Lett. 1977, 15, 56-56.