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  • Simultaneous electropolymerization and electro-click functionalization for highly versatile surface platforms.

Simultaneous electropolymerization and electro-click functionalization for highly versatile surface platforms.

ACS nano (2014-04-18)
Gaulthier Rydzek, Tatyana G Terentyeva, Amir Pakdel, Dmitri Golberg, Jonathan P Hill, Katsuhiko Ariga
ABSTRACT

Simple preparation methods of chemically versatile and highly functionalizable surfaces remain rare and present a challenging research objective. Here, we demonstrate a simultaneous electropolymerization and electro-click functionalization process (SEEC) for one-pot self-construction of aniline- and naphthalene-based functional polymer films where both polymerization and click functionalization are triggered by applying electrochemical stimuli. Cyclic voltammetry (CV) can be applied for the simultaneous oxidation of 4-azidoaniline and the reduction of Cu(II) ions, resulting in polymerization of the former, and the Cu(I)-catalyzed alkyne/azide cycloaddition ("click" chemistry). Properties of the films obtained can be tuned by varying their morphology, their chemically "clicked" content, or by postconstruction functionalization. To demonstrate this, the CV scan rates, component monomers, and "clicked" molecules were varied. Covalent postconstruction immobilization of horseradish peroxidase was also performed. Consequently, pseudocapacitance and enzyme activity were affected. SEEC provides surface scientists an easy access to a wide range of functionalization possibilities in several fields including sensors, fuel cells, photovoltaics, and biomaterials.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Phenylacetylene, 98%
Sigma-Aldrich
Copper(II) sulfate pentahydrate, 99.995% trace metals basis
Supelco
Ethanol solution, certified reference material, 2000 μg/mL in methanol
Sigma-Aldrich
Aniline, ACS reagent, ≥99.5%
Millipore
Hydrogen peroxide solution, 3%, suitable for microbiology
Supelco
Aniline, analytical standard
Supelco
4-Aminoantipyrine, for spectrophotometric det. of H2O2 and phenols, ≥98.0%
Sigma-Aldrich
Copper(II) sulfate pentahydrate, 99.999% trace metals basis
Sigma-Aldrich
Aniline, ReagentPlus®, 99%
Sigma-Aldrich
4-Aminoantipyrine, puriss. p.a., reag. Ph. Eur., ≥99%
Sigma-Aldrich
Hydrogen peroxide solution, contains ~200 ppm acetanilide as stabilizer, 3 wt. % in H2O
Sigma-Aldrich
4-Aminoantipyrine, reagent grade
Sigma-Aldrich
Hydrogen peroxide solution, purum p.a., ≥35% (RT)
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Liquified Phenol, ≥89.0%
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Phenol, BioXtra, ≥99.5% (GC)
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Phenol solution, Saturated with 0.1 M citrate buffer, pH 4.3 ± 0.2, BioReagent, for molecular biology
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Phenol solution, Equilibrated with 10 mM Tris HCl, pH 8.0, 1 mM EDTA, BioReagent, for molecular biology
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Phenol, for molecular biology
Sigma-Aldrich
Phenol, unstabilized, purified by redistillation, ≥99%
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Phenol, unstabilized, ReagentPlus®, ≥99%
Supelco
Phenol, PESTANAL®, analytical standard
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Phenol, puriss., ≥99.5% (GC), meets analytical specification of Ph. Eur., BP, USP, crystalline (detached)
Sigma-Aldrich
Phenol, puriss., meets analytical specification of Ph. Eur., BP, USP, 99.5-100.5% (GC)
Sigma-Aldrich
Phenol, contains hypophosphorous as stabilizer, loose crystals, ACS reagent, ≥99.0%
Sigma-Aldrich
Phenol, ≥99%
Sigma-Aldrich
Phenol, ≥96.0% (calc. on dry substance, T)
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Phenol, BioUltra, for molecular biology, TE-saturated, ~73% (T)
Sigma-Aldrich
Phenol, BioUltra, for molecular biology, ≥99.5% (GC)
Supelco
Phenol solution, 100 μg/mL in acetonitrile, PESTANAL®, analytical standard