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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
4-Aminoantipyrine, reagent grade
Sigma-Aldrich
Copper(II) sulfate pentahydrate, BioReagent, suitable for cell culture, ≥98%
Sigma-Aldrich
Copper(II) sulfate pentahydrate, suitable for plant cell culture, ≥98%
Supelco
Aniline, analytical standard
Millipore
Hydrogen peroxide solution, 3%, suitable for microbiology
Sigma-Aldrich
4-Aminoantipyrine, puriss. p.a., reag. Ph. Eur., ≥99%
Sigma-Aldrich
Copper(II) sulfate pentahydrate, purum p.a., crystallized, ≥99.0% (RT)
Supelco
4-Aminoantipyrine, for spectrophotometric det. of H2O2 and phenols, ≥98.0%
Supelco
Dehydrated Alcohol, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
Aniline, ReagentPlus®, 99%
Sigma-Aldrich
Phenylacetylene, 98%
Sigma-Aldrich
Aniline, ACS reagent, ≥99.5%
Supelco
Ethanol solution, certified reference material, 2000 μg/mL in methanol
Sigma-Aldrich
Copper(II) sulfate pentahydrate, 99.999% trace metals basis
Sigma-Aldrich
Copper(II) sulfate pentahydrate, 99.995% trace metals basis
Sigma-Aldrich
Copper(II) sulfate pentahydrate, puriss., suitable for, meets analytical specification of Ph. Eur., BP, USP,FCC
Sigma-Aldrich
Copper(II) sulfate pentahydrate, ACS reagent, ≥98.0%
Sigma-Aldrich
Copper(II) sulfate pentahydrate, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., 99-102%
Sigma-Aldrich
Copper(II) sulfate pentahydrate, ReagentPlus®, ≥98.0%
Sigma-Aldrich
Hydrogen peroxide solution, contains ~200 ppm acetanilide as stabilizer, 3 wt. % in H2O
Sigma-Aldrich
Zirconyl chloride octahydrate, reagent grade, 98%
USP
Dehydrated Alcohol, United States Pharmacopeia (USP) Reference Standard
Supelco
4-Aminoantipyrine, analytical standard
Sigma-Aldrich
Ethyl alcohol, Pure, 190 proof, for molecular biology
USP
Phenol, United States Pharmacopeia (USP) Reference Standard
Sigma-Aldrich
Ethyl alcohol, Pure, 200 proof, ACS reagent, ≥99.5%
Sigma-Aldrich
Ethyl alcohol, Pure, 200 proof, meets USP testing specifications
Sigma-Aldrich
Ethyl alcohol, Pure, 200 proof, for molecular biology
Sigma-Aldrich
Phenol, puriss. p.a., ACS reagent, reag. Ph. Eur., 99.0-100.5%
Sigma-Aldrich
N-Hydroxysuccinimide, purum, ≥97.0% (T)