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Self-Limited Grafting of Sub-Monolayers via Diels–Alder Reaction on Glassy Carbon Electrodes: An Electrochemical Insight

[Image: see text] The grafting of molecular monolayers is critical for the functionalization of surfaces. In molecular electrochemistry, the surface modification of electrodes and the way molecules are attached to the electrode surface are highly critical to electron transfers and electrochemical re...

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Autores principales: Al Dine, Walaa Nasser, Mehdi, Ahmad, BouMalham, Ibrahim, Herro, Ziad, Vioux, André, Brun, Nicolas, Fontaine, Olivier
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6906774/
https://www.ncbi.nlm.nih.gov/pubmed/31858038
http://dx.doi.org/10.1021/acsomega.9b02391
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author Al Dine, Walaa Nasser
Mehdi, Ahmad
BouMalham, Ibrahim
Herro, Ziad
Vioux, André
Brun, Nicolas
Fontaine, Olivier
author_facet Al Dine, Walaa Nasser
Mehdi, Ahmad
BouMalham, Ibrahim
Herro, Ziad
Vioux, André
Brun, Nicolas
Fontaine, Olivier
author_sort Al Dine, Walaa Nasser
collection PubMed
description [Image: see text] The grafting of molecular monolayers is critical for the functionalization of surfaces. In molecular electrochemistry, the surface modification of electrodes and the way molecules are attached to the electrode surface are highly critical to electron transfers and electrochemical reactions. In this paper, sub-monolayers were covalently grafted onto glassy carbon (GC) electrodes via Diels–Alder cycloaddition with two soluble dienophiles, that is, propargyl bromide and ethynyl ferrocene. Such an approach is clean (no by-product, no catalyst/additive) and occurs under mild conditions by heating at 50 °C in toluene for few hours. The as-modified electrodes were thoroughly characterized by FTIR, XPS, and cyclic voltammetry using both millimetric GC electrodes and ultra-microelectrodes. Cyclic voltammetry gave access to surface coverage and clearly evidenced the covalent grafting of sub-monolayers. The grafting of functional sub-monolayers via Diels–Alder cycloaddition could be easily extended to various functionalities and carbons to prepare electrochemical sensors or electrocatalytic surfaces.
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spelling pubmed-69067742019-12-19 Self-Limited Grafting of Sub-Monolayers via Diels–Alder Reaction on Glassy Carbon Electrodes: An Electrochemical Insight Al Dine, Walaa Nasser Mehdi, Ahmad BouMalham, Ibrahim Herro, Ziad Vioux, André Brun, Nicolas Fontaine, Olivier ACS Omega [Image: see text] The grafting of molecular monolayers is critical for the functionalization of surfaces. In molecular electrochemistry, the surface modification of electrodes and the way molecules are attached to the electrode surface are highly critical to electron transfers and electrochemical reactions. In this paper, sub-monolayers were covalently grafted onto glassy carbon (GC) electrodes via Diels–Alder cycloaddition with two soluble dienophiles, that is, propargyl bromide and ethynyl ferrocene. Such an approach is clean (no by-product, no catalyst/additive) and occurs under mild conditions by heating at 50 °C in toluene for few hours. The as-modified electrodes were thoroughly characterized by FTIR, XPS, and cyclic voltammetry using both millimetric GC electrodes and ultra-microelectrodes. Cyclic voltammetry gave access to surface coverage and clearly evidenced the covalent grafting of sub-monolayers. The grafting of functional sub-monolayers via Diels–Alder cycloaddition could be easily extended to various functionalities and carbons to prepare electrochemical sensors or electrocatalytic surfaces. American Chemical Society 2019-11-27 /pmc/articles/PMC6906774/ /pubmed/31858038 http://dx.doi.org/10.1021/acsomega.9b02391 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Al Dine, Walaa Nasser
Mehdi, Ahmad
BouMalham, Ibrahim
Herro, Ziad
Vioux, André
Brun, Nicolas
Fontaine, Olivier
Self-Limited Grafting of Sub-Monolayers via Diels–Alder Reaction on Glassy Carbon Electrodes: An Electrochemical Insight
title Self-Limited Grafting of Sub-Monolayers via Diels–Alder Reaction on Glassy Carbon Electrodes: An Electrochemical Insight
title_full Self-Limited Grafting of Sub-Monolayers via Diels–Alder Reaction on Glassy Carbon Electrodes: An Electrochemical Insight
title_fullStr Self-Limited Grafting of Sub-Monolayers via Diels–Alder Reaction on Glassy Carbon Electrodes: An Electrochemical Insight
title_full_unstemmed Self-Limited Grafting of Sub-Monolayers via Diels–Alder Reaction on Glassy Carbon Electrodes: An Electrochemical Insight
title_short Self-Limited Grafting of Sub-Monolayers via Diels–Alder Reaction on Glassy Carbon Electrodes: An Electrochemical Insight
title_sort self-limited grafting of sub-monolayers via diels–alder reaction on glassy carbon electrodes: an electrochemical insight
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6906774/
https://www.ncbi.nlm.nih.gov/pubmed/31858038
http://dx.doi.org/10.1021/acsomega.9b02391
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