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

Electrochemical and solid-phase synthetic modification of glassy carbon electrodes with dihydroxybenzene compounds and the electrocatalytic oxidation of NADH
Electrochemical and solid-phase synthetic modification of glassy carbon electrodes with dihydroxybenzene compounds and the electrocatalytic oxidation of NADH
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 C6H4CH2NH linkers. First, Boc-protected EDA or Boc–NHCH2C6H4 were electrochemically attached to the GC surface. After Boc-deprotection, dimethoxybenzoyl chlorides were coupled to the EDA and C6H4CH2NH 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, Emp, 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.
modified electrode, NADH oxidation, dihydroxybenzene, Library, solid-phase synthesis
115-125
Ghanem, Mohamed A.
cef6c814-2709-4a2f-a052-06d28d0ba04c
Chrétien, Jean-Mathieu
ae3cb8ea-7cf0-4ce1-a1d0-1a6fdfe7e311
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a
Bartlett, Philip N.
d99446db-a59d-4f89-96eb-f64b5d8bb075
Ghanem, Mohamed A.
cef6c814-2709-4a2f-a052-06d28d0ba04c
Chrétien, Jean-Mathieu
ae3cb8ea-7cf0-4ce1-a1d0-1a6fdfe7e311
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a
Bartlett, Philip N.
d99446db-a59d-4f89-96eb-f64b5d8bb075

Ghanem, Mohamed A., Chrétien, Jean-Mathieu, Kilburn, Jeremy D. and Bartlett, Philip N. (2009) Electrochemical and solid-phase synthetic modification of glassy carbon electrodes with dihydroxybenzene compounds and the electrocatalytic oxidation of NADH. Bioelectrochemistry, 76 (1-2), 115-125. (doi:10.1016/j.bioelechem.2009.02.008).

Record type: Article

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 C6H4CH2NH linkers. First, Boc-protected EDA or Boc–NHCH2C6H4 were electrochemically attached to the GC surface. After Boc-deprotection, dimethoxybenzoyl chlorides were coupled to the EDA and C6H4CH2NH 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, Emp, 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.

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More information

Published date: September 2009
Keywords: modified electrode, NADH oxidation, dihydroxybenzene, Library, solid-phase synthesis

Identifiers

Local EPrints ID: 145009
URI: http://eprints.soton.ac.uk/id/eprint/145009
PURE UUID: 351510c6-e5b0-4c27-a1b3-192ec37df9af
ORCID for Philip N. Bartlett: ORCID iD orcid.org/0000-0002-7300-6900

Catalogue record

Date deposited: 15 Apr 2010 14:29
Last modified: 17 Sep 2019 01:09

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Contributors

Author: Mohamed A. Ghanem
Author: Jean-Mathieu Chrétien
Author: Jeremy D. Kilburn

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