Electrochemical and solid-phase synthetic modification of glassy carbon electrodes with dihydroxybenzene compounds and the electrocatalytic oxidation of NADH

Mohamed A. Ghanem, Jean-Mathieu Chretien, Jeremy Dunbar Kilburn, Philip N. Bartlett*

*Corresponding author for this work

    Research output: Contribution to journalArticle

    32 Citations (Scopus)

    Abstract

    We report the preparation, using electrochemical and solid-phase synthesis, and characterisation of a 26 member library of 13 dihydroxybenzene derivatives covalently attached to glassy carbon through ethylenediamine (EDA) and C(6)H(4)CH(2)NH- linkers. First, Boc-protected EDA or Boc-NHCH(2)C(6)H(4) were electrochemically attached to the GC surface. After Boc-deprotection, dimethoxybenzoyl chlorides were coupled to the EDA and C(6)H(4)CH(2)NH- linkers using solid-phase synthesis followed by deprotection of the methoxy groups to give the corresponding dihydroxybenzene compounds. Surface coverage and electrochemical parameters of the dihydroxybenzene modified electrodes were evaluated in parallel using cyclic voltammetry. The mid-peak potentials, E(mp), and surface coverages for the 13 dihydroxybenzene derivatives were found to be independent of the choice of linker. The mid-peak potentials of the immobilised dihydroxybenzene derivatives varied between 0.0 and 260 mV vs. SCE and their surface coverages varied between 0.07 and 1.1 nmol cm(-2), depending on the pattern of substitution of the dihydroxybenzene ring. The electrocatalytic activities of the library were evaluated for mediation of NADH oxidation, and the ortho-dihydroxybenzene derivatives were found to have higher catalytic activity. (C) 2009 Elsevier B.V. All rights reserved.

    Original languageEnglish
    Pages (from-to)115-125
    Number of pages11
    JournalBioelectrochemistry
    Volume76
    Issue number1-2
    DOIs
    Publication statusPublished - Sep 2009

    Keywords

    • Modified electrode
    • NADH oxidation
    • Dihydroxybenzene
    • Library
    • Solid-phase synthesis
    • DIHYDRONICOTINAMIDE ADENINE-DINUCLEOTIDE
    • DIAZONIUM SALTS
    • COVALENT MODIFICATION
    • GRAPHITE-ELECTRODES
    • SYNTHESIS METHODOLOGIES
    • CATALYTIC-OXIDATION
    • SURFACES
    • REDUCTION
    • ADSORPTION
    • ATTACHMENT

    Cite this

    Electrochemical and solid-phase synthetic modification of glassy carbon electrodes with dihydroxybenzene compounds and the electrocatalytic oxidation of NADH. / Ghanem, Mohamed A.; Chretien, Jean-Mathieu; Kilburn, Jeremy Dunbar; Bartlett, Philip N.

    In: Bioelectrochemistry, Vol. 76, No. 1-2, 09.2009, p. 115-125.

    Research output: Contribution to journalArticle

    Ghanem, Mohamed A. ; Chretien, Jean-Mathieu ; Kilburn, Jeremy Dunbar ; Bartlett, Philip N. / Electrochemical and solid-phase synthetic modification of glassy carbon electrodes with dihydroxybenzene compounds and the electrocatalytic oxidation of NADH. In: Bioelectrochemistry. 2009 ; Vol. 76, No. 1-2. pp. 115-125.
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    abstract = "We report the preparation, using electrochemical and solid-phase synthesis, and characterisation of a 26 member library of 13 dihydroxybenzene derivatives covalently attached to glassy carbon through ethylenediamine (EDA) and C(6)H(4)CH(2)NH- linkers. First, Boc-protected EDA or Boc-NHCH(2)C(6)H(4) were electrochemically attached to the GC surface. After Boc-deprotection, dimethoxybenzoyl chlorides were coupled to the EDA and C(6)H(4)CH(2)NH- linkers using solid-phase synthesis followed by deprotection of the methoxy groups to give the corresponding dihydroxybenzene compounds. Surface coverage and electrochemical parameters of the dihydroxybenzene modified electrodes were evaluated in parallel using cyclic voltammetry. The mid-peak potentials, E(mp), and surface coverages for the 13 dihydroxybenzene derivatives were found to be independent of the choice of linker. The mid-peak potentials of the immobilised dihydroxybenzene derivatives varied between 0.0 and 260 mV vs. SCE and their surface coverages varied between 0.07 and 1.1 nmol cm(-2), depending on the pattern of substitution of the dihydroxybenzene ring. The electrocatalytic activities of the library were evaluated for mediation of NADH oxidation, and the ortho-dihydroxybenzene derivatives were found to have higher catalytic activity. (C) 2009 Elsevier B.V. All rights reserved.",
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    T1 - Electrochemical and solid-phase synthetic modification of glassy carbon electrodes with dihydroxybenzene compounds and the electrocatalytic oxidation of NADH

    AU - Ghanem, Mohamed A.

    AU - Chretien, Jean-Mathieu

    AU - Kilburn, Jeremy Dunbar

    AU - Bartlett, Philip N.

    PY - 2009/9

    Y1 - 2009/9

    N2 - We report the preparation, using electrochemical and solid-phase synthesis, and characterisation of a 26 member library of 13 dihydroxybenzene derivatives covalently attached to glassy carbon through ethylenediamine (EDA) and C(6)H(4)CH(2)NH- linkers. First, Boc-protected EDA or Boc-NHCH(2)C(6)H(4) were electrochemically attached to the GC surface. After Boc-deprotection, dimethoxybenzoyl chlorides were coupled to the EDA and C(6)H(4)CH(2)NH- linkers using solid-phase synthesis followed by deprotection of the methoxy groups to give the corresponding dihydroxybenzene compounds. Surface coverage and electrochemical parameters of the dihydroxybenzene modified electrodes were evaluated in parallel using cyclic voltammetry. The mid-peak potentials, E(mp), and surface coverages for the 13 dihydroxybenzene derivatives were found to be independent of the choice of linker. The mid-peak potentials of the immobilised dihydroxybenzene derivatives varied between 0.0 and 260 mV vs. SCE and their surface coverages varied between 0.07 and 1.1 nmol cm(-2), depending on the pattern of substitution of the dihydroxybenzene ring. The electrocatalytic activities of the library were evaluated for mediation of NADH oxidation, and the ortho-dihydroxybenzene derivatives were found to have higher catalytic activity. (C) 2009 Elsevier B.V. All rights reserved.

    AB - We report the preparation, using electrochemical and solid-phase synthesis, and characterisation of a 26 member library of 13 dihydroxybenzene derivatives covalently attached to glassy carbon through ethylenediamine (EDA) and C(6)H(4)CH(2)NH- linkers. First, Boc-protected EDA or Boc-NHCH(2)C(6)H(4) were electrochemically attached to the GC surface. After Boc-deprotection, dimethoxybenzoyl chlorides were coupled to the EDA and C(6)H(4)CH(2)NH- linkers using solid-phase synthesis followed by deprotection of the methoxy groups to give the corresponding dihydroxybenzene compounds. Surface coverage and electrochemical parameters of the dihydroxybenzene modified electrodes were evaluated in parallel using cyclic voltammetry. The mid-peak potentials, E(mp), and surface coverages for the 13 dihydroxybenzene derivatives were found to be independent of the choice of linker. The mid-peak potentials of the immobilised dihydroxybenzene derivatives varied between 0.0 and 260 mV vs. SCE and their surface coverages varied between 0.07 and 1.1 nmol cm(-2), depending on the pattern of substitution of the dihydroxybenzene ring. The electrocatalytic activities of the library were evaluated for mediation of NADH oxidation, and the ortho-dihydroxybenzene derivatives were found to have higher catalytic activity. (C) 2009 Elsevier B.V. All rights reserved.

    KW - Modified electrode

    KW - NADH oxidation

    KW - Dihydroxybenzene

    KW - Library

    KW - Solid-phase synthesis

    KW - DIHYDRONICOTINAMIDE ADENINE-DINUCLEOTIDE

    KW - DIAZONIUM SALTS

    KW - COVALENT MODIFICATION

    KW - GRAPHITE-ELECTRODES

    KW - SYNTHESIS METHODOLOGIES

    KW - CATALYTIC-OXIDATION

    KW - SURFACES

    KW - REDUCTION

    KW - ADSORPTION

    KW - ATTACHMENT

    U2 - 10.1016/j.bioelechem.2009.02.008

    DO - 10.1016/j.bioelechem.2009.02.008

    M3 - Article

    VL - 76

    SP - 115

    EP - 125

    JO - Bioelectrochemistry

    JF - Bioelectrochemistry

    SN - 1567-5394

    IS - 1-2

    ER -