Functionalizing poly(cyclic olefins) using copper-catalyzed azide-alkyne "click" reactions

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DOIResolve DOI: http://doi.org/10.1139/v11-015
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TypeArticle
Journal titleCanadian Journal of Chemistry
ISSN0008-4042
Volume89
Issue5
Pages608615; # of pages: 8
Subjectclick chemistry; Click reaction; Cyclic olefins; Cycloadditions; Functionalizations; Functionalized; Hydrophilic properties; Modified surfaces; oxygen plasma; Oxygen plasma treatments; Ozonolysis; Robust methods; Water contact angle measurement; Zeonor; Acetylene; Amides; Angle measurement; Atomic force microscopy; Atomic spectroscopy; Carboxylic acids; Catalysis; Contact angle; Fluorescence microscopy; Olefins; Ozone; Photoelectron spectroscopy; Plasma applications; X ray photoelectron spectroscopy; Surfaces
AbstractA robust method for functionalizing poly(cyclic olefin) surfaces comprised of Zeonor 1060R was developed. These surfaces were first oxidized using two separate methods, ozonolysis and oxygen plasma treatment, to increase their hydrophilic properties and produce carboxylic acids on the surface. The resulting acids enabled direct amide coupling with various amines containing azide or alkyne moieties onto the surface. These modified surfaces were further functionalized via copper-catalyzed azide-alkyne cycloadditions (CuAAC) on the surface and the method was optimized for this material. Surface modifications were characterized by water contact angle measurements, fluorescence microscopy, atomic force microscopy, and X-ray photoelectron spectroscopy. Our data demonstrates a robust method for generating "clickable" Zeonor 1060R surfaces as demonstrated through attachment and subsequent detection of a triazole-linked fluorophore. The method developed enables the systematic modification of any poly(cyclic olefin) surface for functionalization using the click reaction. © 2011 Published by NRC Research Press.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC); NRC Steacie Institute for Molecular Sciences (SIMS-ISSM); NRC Industrial Materials Institute (IMI-IMI)
Peer reviewedYes
NPARC number21271358
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Record identifier4b2ae1c9-99b0-462b-8c0b-b9cdfb3ae153
Record created2014-03-24
Record modified2016-05-09
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