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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-Ethynylbenzaldehyde, 97%
Supelco
Phenol solution, certified reference material, 500 μg/mL in methanol
Sigma-Aldrich
Phenol, unstabilized, ReagentPlus®, ≥99%
Sigma-Aldrich
4-Ethynylaniline, 97%
Sigma-Aldrich
Phenol, unstabilized, purified by redistillation, ≥99%
Sigma-Aldrich
Copper(II) chloride, anhydrous, powder, ≥99.995% trace metals basis
Sigma-Aldrich
Phenol, ≥99.0%
Sigma-Aldrich
Copper(II) chloride, SAJ first grade, ≥98.0%
Sigma-Aldrich
Ethanol, ≥99.5%, suitable for absorption spectrum analysis
Sigma-Aldrich
Ethanol, ≥99.5%, suitable for HPLC
Sigma-Aldrich
Ethanol, ≥99.5%
Sigma-Aldrich
Phenol, SAJ first grade, ≥98.0%
Sigma-Aldrich
Phenol, ≥99.0%
Sigma-Aldrich
Ethyl alcohol, Pure, 200 proof, anhydrous, ≥99.5%
Supelco
Phenol solution, 5000 μg/mL in methanol, certified reference material
Sigma-Aldrich
Ethanol, ≥99.5%, suitable for fluorescence
Sigma-Aldrich
Ethanol, ≥99.5%, SAJ super special grade
Sigma-Aldrich
Phenol, JIS special grade, ≥99.0%
Sigma-Aldrich
10-Undecynoic acid, 95%
Sigma-Aldrich
Ethanol, purum, fine spirit, denaturated with 4.8% methanol, F25 METHYL1, ~96% (based on denaturant-free substance)
Sigma-Aldrich
Ethanol, ACS reagent, prima fine spirit, without additive, F15 o1
Sigma-Aldrich
Ethanol, purum, absolute ethanol, denaturated with 2% 2-butanone, A15 MEK1, ≥99.8% (based on denaturant-free substance)
Sigma-Aldrich
Ethanol, puriss. p.a., absolute, ≥99.8% (GC)
Sigma-Aldrich
Phenol, natural, 97%, FG
Supelco
Phenol, Pharmaceutical Secondary Standard; Certified Reference Material
USP
Phenol, United States Pharmacopeia (USP) Reference Standard
Sigma-Aldrich
Ethyl alcohol, Pure, 200 proof
Sigma-Aldrich
Ethyl alcohol, Pure, 200 proof, ACS reagent, ≥99.5%
Sigma-Aldrich
Ethyl alcohol, Pure, 200 proof, meets USP testing specifications
Sigma-Aldrich
Phenol, BioXtra, ≥99.5% (GC)