Electrochemical Functionalization of Carbon Surfaces by Aromatic Azide or Alkyne Molecules: A Versatile Platform for Click Chemistry
- 10 October 2008
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 14 (30), 9286-9291
- https://doi.org/10.1002/chem.200801168
Abstract
The electrochemical reduction of phenylazide or phenylacetylene diazonium salts leads to the grafting of azido or ethynyl groups onto the surface of carbon electrodes. In the presence of copper(I) catalyst, these azide- or alkyne-modified surfaces react efficiently and rapidly with compounds bearing an acetylene or azide function, thus forming a covalent 1,2,3-triazole linkage by means of click chemistry. This was illustrated with the surface coupling of ferrocenes functionalized with an ethynyl or azido group and the biomolecule biotin terminated by an acetylene group.This publication has 39 references indexed in Scilit:
- Reversible Photoregulation of Binding of α-Chymotrypsin to a Gold SurfaceJournal of the American Chemical Society, 2007
- A Versatile Method for Direct and Covalent Immobilization of DNA and Proteins on BiochipsAngewandte Chemie, 2007
- A Cytochrome c Oxidase Model Catalyzes Oxygen to Water Reduction Under Rate-Limiting Electron FluxScience, 2007
- The pyrolytic graphite surface as an enzyme substrate: microscopic and spectroscopic studiesJournal of Solid State Electrochemistry, 2006
- Solar Energy Conversion by Dye-Sensitized Photovoltaic CellsInorganic Chemistry, 2005
- Mechanism of the Ligand‐Free CuI‐Catalyzed Azide–Alkyne Cycloaddition ReactionAngewandte Chemie, 2005
- Self-Assembled Monolayers of Thiolates on Metals as a Form of NanotechnologyChemical Reviews, 2005
- Dense Monolayers of Metal-Chelating Ligands Covalently Attached to Carbon Electrodes Electrochemically and Their Useful Application in Affinity Binding of Histidine-Tagged ProteinsLangmuir, 2005
- Biotinylation of Screen-Printed Carbon Electrodes through the Electrochemical Reduction of the Diazonium Salt of p-Aminobenzoyl BiocytinJournal of the American Chemical Society, 1999
- Covalent Modification of Carbon Surfaces by Aryl Radicals Generated from the Electrochemical Reduction of Diazonium SaltsJournal of the American Chemical Society, 1997