The University of Southampton
University of Southampton Institutional Repository

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
Covalent tethering of organic functionality to the surface of glassy carbon electrodes by using electrochemical and solid-phase synthesis methodologies
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--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.
surface chemistry, multilayers, solid-phase synthesis, reduction, spectrophotometric determination, oxidation, electrochemistry, quinones, alkaline-solution, electroreduction, acidity constants, anthraquinone, oxygen, diazonium salts, cyclic voltammetry
0947-6539
2548-2556
Chretien, Jean-Mathieu
c1a0c265-0262-4d54-b8b2-0d05d8f58dd7
Ghanem, Mohamed A.
cef6c814-2709-4a2f-a052-06d28d0ba04c
Bartlett, Philip N.
d99446db-a59d-4f89-96eb-f64b5d8bb075
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a
Chretien, Jean-Mathieu
c1a0c265-0262-4d54-b8b2-0d05d8f58dd7
Ghanem, Mohamed A.
cef6c814-2709-4a2f-a052-06d28d0ba04c
Bartlett, Philip N.
d99446db-a59d-4f89-96eb-f64b5d8bb075
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a

Chretien, Jean-Mathieu, Ghanem, Mohamed A., Bartlett, Philip N. and Kilburn, Jeremy D. (2008) Covalent tethering of organic functionality to the surface of glassy carbon electrodes by using electrochemical and solid-phase synthesis methodologies. Chemistry - A European Journal, 14 (8), 2548-2556. (doi:10.1002/chem.200701559).

Record type: Article

Abstract

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--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.

Full text not available from this repository.

More information

Submitted date: 3 October 2007
Published date: 7 March 2008
Keywords: surface chemistry, multilayers, solid-phase synthesis, reduction, spectrophotometric determination, oxidation, electrochemistry, quinones, alkaline-solution, electroreduction, acidity constants, anthraquinone, oxygen, diazonium salts, cyclic voltammetry

Identifiers

Local EPrints ID: 54436
URI: https://eprints.soton.ac.uk/id/eprint/54436
ISSN: 0947-6539
PURE UUID: d2fb2962-d2e9-4760-a0b8-468642fcd2d0
ORCID for Philip N. Bartlett: ORCID iD orcid.org/0000-0002-7300-6900

Catalogue record

Date deposited: 06 Aug 2008
Last modified: 14 Mar 2019 01:53

Export record

Altmetrics

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of https://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×