Functionalization of Carbon Surfaces Using the Copper-Catalyzed Diels-Alder Reaction

Abstract

We propose here a new method to functionalize carbonmaterials via a catalyzed Diels-Alder reaction.In a Diels-Alderreaction, carbon materials can be used as a diene or a dienophile.Here, carbon materials are used as dienes and alkyne-terminated derivativesas dienophiles. Different carbon materials, i.e., glassy carbon, carbonpowder (carbon black), pyrolytic graphite carbon materials, and graphene,were functionalized by alkyne ferrocene derivatives or perfluoro-taggedalkyne molecules and characterized by electrochemical means, atomicforce microscopy, and X-ray photoelectron spectroscopy experiments.This method allows for the rapid functionalization of carbon materialsin mild conditions with high surface coverage.