Covalent tethering of organic functionality to the surface of glassy carbon electrodes by using electrochemical and solid-phase synthesis methodologies

Chemistry : a European Journal
Jean-Mathieu ChrétienJeremy D Kilburn

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-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.

Citations

Dec 5, 2015·Chemistry : a European Journal·Jessica GroppiJeremy D Kilburn
Jun 26, 2010·Physical Chemistry Chemical Physics : PCCP·Maciej SosnaPhilip N Bartlett
Dec 2, 2010·Nature Communications·Eric StruyfPatrick Meire
Apr 20, 2011·Chemical Society Reviews·Daniel Bélanger, Jean Pinson
Mar 27, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Alejandra M RicciErnesto J Calvo
Jan 12, 2020·Materials Science & Engineering. C, Materials for Biological Applications·Rabih Khoder, Hafsa Korri-Youssoufi
Jan 5, 2021·Analytical Sciences : the International Journal of the Japan Society for Analytical Chemistry·Mutsuo Tanaka, Osamu Niwa
Dec 2, 2010·Langmuir : the ACS Journal of Surfaces and Colloids·Mutsuo TanakaOsamu Niwa
Oct 11, 2012·Journal of the American Chemical Society·Aleksandra PinczewskaPhilip N Bartlett
Apr 16, 2015·Langmuir : the ACS Journal of Surfaces and Colloids·Lita LeeAlison J Downard
Feb 20, 2020·Langmuir : the ACS Journal of Surfaces and Colloids·M GabajiJ P Michel

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