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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

USP
Phenol, United States Pharmacopeia (USP) Reference Standard
Sigma-Aldrich
Phenol, natural, 97%, FG
Sigma-Aldrich
Ethanol, purum, fine spirit, denaturated with 4.8% methanol, F25 METHYL1, ~96% (based on denaturant-free substance)
Sigma-Aldrich
Ethyl alcohol, Pure 200 proof, Molecular Biology
Sigma-Aldrich
Ethyl alcohol, Pure, 200 proof, meets USP testing specifications
Sigma-Aldrich
Ethyl alcohol, Pure, 200 proof, ACS reagent, ≥99.5%
Sigma-Aldrich
4-Ethynylbenzaldehyde, 97%
Supelco
Phenol solution, 5000 μg/mL in methanol, certified reference material
Supelco
Phenol solution, certified reference material, 500 μg/mL in methanol
Sigma-Aldrich
Copper(II) chloride, 99.999% trace metals basis
Sigma-Aldrich
Ethyl alcohol, Pure, 200 proof, anhydrous, ≥99.5%
Sigma-Aldrich
Copper(II) chloride, anhydrous, powder, ≥99.995% trace metals basis
Sigma-Aldrich
Ethanol, absolute, sales not in Germany, ≥99.8% (vol.)
Sigma-Aldrich
Copper(II) chloride, powder, 99%
Sigma-Aldrich
N-Hydroxysuccinimide, 98%
Sigma-Aldrich
Phenol, ACS reagent, ≥99.0%
Sigma-Aldrich
10-Undecynoic acid, 95%
Sigma-Aldrich
Phenol, ≥99%
Sigma-Aldrich
Copper(II) chloride, 97%
Sigma-Aldrich
Phenol, unstabilized, ReagentPlus®, ≥99%
Sigma-Aldrich
4-Ethynylaniline, 97%
Sigma-Aldrich
Phenol, unstabilized, purified by redistillation, ≥99%
Supelco
Phenol solution, 100 μg/mL in acetonitrile, PESTANAL®, analytical standard
Sigma-Aldrich
Phenol, ≥96.0% (calc. on dry substance, T)
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Ethynylferrocene, 97%
Sigma-Aldrich
Phenol, BioUltra, Molecular Biology, ≥99.5% (GC)
Sigma-Aldrich
Phenol, BioUltra, Molecular Biology, TE-saturated, ~73% (T)
Supelco
Phenol, PESTANAL®, analytical standard
Sigma-Aldrich
N-Hydroxysuccinimide, purum, ≥97.0% (T)
Sigma-Aldrich
Phenol, puriss., meets analytical specification of Ph. Eur., BP, USP, ≥99.5% (GC), crystalline (detached)