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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
Hydrogen peroxide solution, 34.5-36.5%
Supelco
4-Aminoantipyrine, for spectrophotometric det. of H2O2 and phenols, ≥98.0%
Supelco
Aniline, analytical standard
Sigma-Aldrich
Hydrogen peroxide solution, contains potassium stannate as inhibitor, 30-32 wt. % in water, semiconductor grade, 99.999% trace metals basis
Sigma-Aldrich
Phenylacetylene, 98%
Sigma-Aldrich
Hydrogen peroxide solution, tested according to Ph. Eur.
Sigma-Aldrich
4-Aminoantipyrine, puriss. p.a., reag. Ph. Eur., ≥99%
Supelco
4-Aminoantipyrine, analytical standard
Supelco
Dehydrated Alcohol, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
Copper(II) sulfate pentahydrate, JIS special grade, ≥99.5%
Supelco
Ethanol solution, certified reference material, 2000 μg/mL in methanol
Sigma-Aldrich
Aniline, JIS special grade, ≥99.0%
Sigma-Aldrich
Aniline, SAJ first grade, ≥99.0%
Sigma-Aldrich
Copper(II) sulfate pentahydrate, 99.999% trace metals basis
Sigma-Aldrich
Aniline, ReagentPlus®, 99%
USP
Dehydrated Alcohol, United States Pharmacopeia (USP) Reference Standard
Sigma-Aldrich
4-Aminoantipyrine, ≥99.0%, JIS special grade
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Hydrogen Peroxide Solution, 30% (w/w), puriss. p.a., reag. ISO, reag. Ph. Eur.
Sigma-Aldrich
Zirconyl chloride octahydrate, reagent grade, 98%
Sigma-Aldrich
Hydrogen peroxide solution, contains ~200 ppm acetanilide as stabilizer, 3 wt. % in H2O
Sigma-Aldrich
Hydrogen peroxide solution, contains inhibitor, 30 wt. % in H2O, ACS reagent
Sigma-Aldrich
Hydrogen peroxide solution, contains inhibitor, 35 wt. % in H2O
Sigma-Aldrich
Copper(II) sulfate pentahydrate, puriss., suitable for, meets analytical specification of Ph. Eur., BP, USP,FCC
Sigma-Aldrich
Hydrogen peroxide solution, purum p.a., ≥35% (RT)
Sigma-Aldrich
Copper(II) sulfate pentahydrate, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., 99-102%
Sigma-Aldrich
Hydrogen peroxide solution, 50 wt. % in H2O, stabilized
Sigma-Aldrich
Copper(II) sulfate pentahydrate, ReagentPlus®, ≥98.0%
Sigma-Aldrich
Copper(II) sulfate pentahydrate, ACS reagent, ≥98.0%
Sigma-Aldrich
Hydrogen peroxide solution, contains inhibitor, 30 wt. % in H2O, meets USP testing specifications