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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
Hydrogen peroxide solution, contains ~200 ppm acetanilide as stabilizer, 3 wt. % in H2O
Millipore
Hydrogen peroxide solution, 3%, suitable for microbiology
Supelco
Aniline, analytical standard
Supelco
Dehydrated Alcohol, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
Ethanol, BioUltra, for molecular biology, ≥99.8%, (absolute alcohol, without additive, A15 o1)
Supelco
Phenol, Pharmaceutical Secondary Standard; Certified Reference Material
USP
Dehydrated Alcohol, United States Pharmacopeia (USP) Reference Standard
Supelco
4-Aminoantipyrine, analytical standard
Sigma-Aldrich
Copper(II) sulfate pentahydrate, puriss., suitable for, meets analytical specification of Ph. Eur., BP, USP,FCC
Sigma-Aldrich
Copper(II) sulfate pentahydrate, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., 99-102%
USP
Phenol, United States Pharmacopeia (USP) Reference Standard
Sigma-Aldrich
Copper(II) sulfate pentahydrate, ACS reagent, ≥98.0%
Sigma-Aldrich
Copper(II) sulfate pentahydrate, ReagentPlus®, ≥98.0%
Sigma-Aldrich
Ethanol, puriss. p.a., absolute, ≥99.8% (GC)
Sigma-Aldrich
Phenol, natural, 97%, FG
Supelco
Ethanol standards 10% (v/v), 10 % (v/v) in H2O, analytical standard
Sigma-Aldrich
Ethanol Fixative 80% v/v, suitable for fixing solution (blood films)
Sigma-Aldrich
Phenol, for molecular biology
Sigma-Aldrich
Copper(II) sulfate pentahydrate, suitable for plant cell culture, ≥98%
Sigma-Aldrich
Phenol, BioXtra, ≥99.5% (GC)
Sigma-Aldrich
Copper(II) sulfate pentahydrate, BioReagent, suitable for cell culture, ≥98%
Sigma-Aldrich
Copper(II) sulfate pentahydrate, purum p.a., crystallized, ≥99.0% (RT)
Sigma-Aldrich
Liquified Phenol, ≥89.0%
Sigma-Aldrich
4-Aminoantipyrine, reagent grade
Sigma-Aldrich
Phenol solution, Saturated with 0.1 M citrate buffer, pH 4.3 ± 0.2, BioReagent, for molecular biology
Sigma-Aldrich
Phenol solution, Equilibrated with 10 mM Tris HCl, pH 8.0, 1 mM EDTA, BioReagent, for molecular biology
Supelco
4-Aminoantipyrine, for spectrophotometric det. of H2O2 and phenols, ≥98.0%
Sigma-Aldrich
4-Aminoantipyrine, puriss. p.a., reag. Ph. Eur., ≥99%
Sigma-Aldrich
Phenol, puriss., meets analytical specification of Ph. Eur., BP, USP, 99.5-100.5% (GC)