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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

Supelco
Dehydrated Alcohol, Pharmaceutical Secondary Standard; Certified Reference Material
Supelco
4-Aminoantipyrine, analytical standard
Sigma-Aldrich
Copper(II) sulfate pentahydrate, purum p.a., crystallized, ≥99.0% (RT)
Sigma-Aldrich
Aniline, ReagentPlus®, 99%
Sigma-Aldrich
Copper(II) sulfate pentahydrate, 99.999% trace metals basis
Sigma-Aldrich
Aniline, ACS reagent, ≥99.5%
Supelco
4-Aminoantipyrine, for spectrophotometric det. of H2O2 and phenols, ≥98.0%
Millipore
Hydrogen peroxide solution, 3%, suitable for microbiology
Sigma-Aldrich
4-Aminoantipyrine, puriss. p.a., reag. Ph. Eur., ≥99%
Supelco
Aniline, analytical standard
Supelco
Ethanol solution, certified reference material, 2000 μg/mL in methanol
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Phenylacetylene, 98%
Sigma-Aldrich
Copper(II) sulfate pentahydrate, 99.995% trace metals basis
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4-Aminoantipyrine, reagent grade
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Copper(II) sulfate pentahydrate, suitable for plant cell culture, ≥98%
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Copper(II) sulfate pentahydrate, BioReagent, suitable for cell culture, ≥98%
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Copper(II) sulfate pentahydrate, ReagentPlus®, ≥98.0%
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Hydrogen peroxide solution, purum p.a., ≥35% (RT)
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Hydrogen peroxide solution, contains ~200 ppm acetanilide as stabilizer, 3 wt. % in H2O
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Zirconyl chloride octahydrate, reagent grade, 98%
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Copper(II) sulfate pentahydrate, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., 99-102%
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Copper(II) sulfate pentahydrate, puriss., suitable for, meets analytical specification of Ph. Eur., BP, USP,FCC
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Copper(II) sulfate pentahydrate, ACS reagent, ≥98.0%
Supelco
Phenol solution, certified reference material, 500 μg/mL in methanol
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Ethanol, BioUltra, for molecular biology, ≥99.8%, (absolute alcohol, without additive, A15 o1)
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4-Ethynylbenzaldehyde, 97%
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Copper(II) chloride, powder, 99%
Supelco
Phenol solution, 5000 μg/mL in methanol, certified reference material
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Ethanol, purum, secunda spirit, denaturated with 2% 2-butanone, S15, ~96% (based on denaturant-free substance)
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Phenol, unstabilized, purified by redistillation, ≥99%