Immobilization of glucose oxidase on a carbon surface derivatized by electrochemical reduction of diazonium salts

Bourdillon, Christian; Delamar, Michel; Demaille, Christophe; Hitmi, Rachid; Moiroux, Jacques; Pinson, Jean

doi:10.1016/0022-0728(92)80266-7

Cited by 184 publications

(138 citation statements)

References 25 publications

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“…[1,2] These attachment methods show good reproducibility, and the covalently bonded organic layers produced by them were found to be stable for long-term storage and upon sonication in aggressive solvents. [8] Further chemical modification can be performed on the electrodes through specific substituents (e.g., ÀCOOH, [9] ÀSO 3 H, [9] ÀNMe 2 [9] or À CH 2 Cl [10,11] ) present on the aromatic ring and used to bond metal complexes, [9] enzymes, [12] or as potential supports for combinatorial chemistry. [10] Of particular relevance to our work described here, Pinson, SavØant et al attached both pnitrophenol and p-acetamidophenyl radicals onto a carbon surface using diazonium salts.…”

Section: Introductionmentioning

confidence: 99%

Covalent Tethering of Organic Functionality to the Surface of Glassy Carbon Electrodes by Using Electrochemical and Solid‐Phase Synthesis Methodologies

Chrétien

Ghanem

Bartlett

et al. 2008

Chemistry A European J

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Organic linkers such as (N-Boc-aminomethyl)phenyl (BocNHCH2C6H4) and N-Boc-ethylenediamine (Boc-EDA) have been covalently tethered onto a glassy carbon surface by employing electrochemical reduction of BocNHCH2C6H4 diazonium salt or oxidation of Boc-EDA. After removal of the Boc group, anthraquinone as a redox model was attached to the linker by a solid-phase coupling reaction. Grafting of anthraquinone to electrodes bearing a second spacer such as 4-(N-Boc-aminomethyl)benzoic acid or N-Boc-beta-alanine was also performed by following this methodology. The surface coverage, stability and electron transfer to/from the tethered anthraquinone redox group through the linkers were investigated by cyclic voltammetry. The effects of pH and scan rate were studied, and the electron-transfer coefficient and rate constant were determined by using Laviron's equation for the different types of linker. The combination of electrochemical attachment of protected linkers and subsequent modifications under the conditions of solid-phase synthesis provides a very versatile methodology for tailoring a wide range of organic functional arrangements on a glassy carbon surface.

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Section: Introductionmentioning

confidence: 99%

Covalent Tethering of Organic Functionality to the Surface of Glassy Carbon Electrodes by Using Electrochemical and Solid‐Phase Synthesis Methodologies

Chrétien

Ghanem

Bartlett

et al. 2008

Chemistry A European J

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“…A mechanism for polyphenylene film formation on electroconductive surfaces (Fe, Cu and Zn) by electrochemical reduction of benzenediazonium tetrafluoroborate in acetonitrile has been proposed by Adenier et al [11]. The free radicals generated during diazonium salts' electrochemical reduction can be used to determine β-cyclodextrin [12,13]; for covalent immobilization of glucose oxidase [14]; for the modification of silicon [15−18] and carbon fiber surfaces [19], as well as single-and multi-walled carbon nanotubes [20−23]; for the surface functionalization of ultrananocrystalline diamond films [24]; for corrosion protection of steel [25]; and for surface modification of polycrystalline gold electrodes [26,27].…”

Section: Central European Journal Of Chemistrymentioning

confidence: 99%

Reaction of metals with benzenediazonium tetrafluoroborate in aprotic solvents

et al. 2010

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“…13,14) The latter method was shown to be effective as the initial derivatization tool for preparing glucose oxidase-modified GC electrodes. 15) We examined whether our own method can be practically applied for preparation of GC electrodes modified with amino compounds. For this purpose, 4-amino-2,2,6,6-tetramethylpiperidinyl-1-oxyl (4-amino-TEMPO) was chosen as an amino compound since the efficiency for immobilizing TEMPO or its analogue on electrode surfaces has been conveniently evaluated by cyclic voltammetry for the electrodes modified by a self-assembly technique 16) and polymer film coating methods.…”

mentioning

confidence: 99%

Anodization in Oligo (Ethylene Glycol) as an Initial Derivatization Tool for Preparing Glassy Carbon Electrodes Covalently Modified with Amino Compounds: Effective Access to a 2,2,6,6-Tetramethylpiperidinyl-1-oxyl (TEMPO)-Modified Glassy Carbon Electrode.

Maeda

Saka-Iri

Ogasawara

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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Anodization in HO(CH 2 CH 2 O) n H (1a, n‫;2؍‬ 1b, n‫;3؍‬ 1c, n‫)4؍‬ as an initial derivatization tool for preparing glassy carbon (GC) electrodes covalently modified with amino compounds was explored. As an amino compound to be immobilized, 4-amino-2,2,6,6-tetramethylpiperidinyl-1-oxyl (4-amino-TEMPO) was selected. When GC electrodes anodized at 2.0 V vs. Ag wire coated with AgCl in 1 containing RCH 2 CH 2 SO 3 Na (2a, R‫؍‬H; 2b, R‫؍‬OH) were treated with a N,N-dimethylformamide (DMF) or CH 2 Cl 2 solution of 4-amino-TEMPO and 1,3-dicyclohexylcarbodiimide (DCC), TEMPO-modified GC electrodes were afforded. Coverage (G G TEMPO ) of the electrode surfaces by TEMPO was estimated by cyclic voltammetry in CH 3 CN containing NaClO 4 . A TEMPO-modified GC electrode with the best G G TEMPO (1.36؋10 ؊10 mol/cm 2 ) was obtained by anodization in 1b containing 2a at the expense of 3.0 C followed by amidization in DMF for 7 d. On cyclic voltammetry, the TEMPO-modified GC electrode showed good and stable electrocatalytic ability for oxidation of allyl alcohol in the presence of 2,6-lutidine.

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Immobilization of glucose oxidase on a carbon surface derivatized by electrochemical reduction of diazonium salts

Cited by 184 publications

References 25 publications

Covalent Tethering of Organic Functionality to the Surface of Glassy Carbon Electrodes by Using Electrochemical and Solid‐Phase Synthesis Methodologies

Covalent Tethering of Organic Functionality to the Surface of Glassy Carbon Electrodes by Using Electrochemical and Solid‐Phase Synthesis Methodologies

Reaction of metals with benzenediazonium tetrafluoroborate in aprotic solvents

Anodization in Oligo (Ethylene Glycol) as an Initial Derivatization Tool for Preparing Glassy Carbon Electrodes Covalently Modified with Amino Compounds: Effective Access to a 2,2,6,6-Tetramethylpiperidinyl-1-oxyl (TEMPO)-Modified Glassy Carbon Electrode.

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