Reductive Arylation of Graphene: Insights into a Reversible Carbon Allotrope Functionalization Reaction

TL;DR

This study investigates the reductive arylation of graphene, revealing how the charge density in graphite intercalation compounds influences functionalization levels and providing insights into the covalent bonding and reversibility of the process.

Contribution

It offers new spectroscopic insights into how negative charges in GICs affect graphene functionalization and the thermal stability of covalent bonds formed during reductive arylation.

Findings

Charge density correlates with degree of functionalization.

Thermal analysis reveals details of covalent bond stability.

Spectroscopic data elucidate the defunctionalization process.

Abstract

The covalent functionalization of graphene represents a main topic in the growing field of nano materials. The reductive exfoliation of graphite with concomitant functionalization of the respective graphenide intermediates provides a promising approach towards functional graphene derivatives. In this article, we present new insights into the reductive arylation of graphene. Graphite intercalation compounds (GICs) with varying stoichiometries have been used as starting materials. Based on the spectroscopic data obtained by scanning Raman microscopy (SRM) and thermogravimetric analysis coupled to mass spectrometry (TG/MS), a clear correlation between the amount of negative charges - present in the GIC - and the degree of functionalization in the final product could be found. Furthermore, the detailed analysis of the thermal defunctionalization process provided deeper insights into the covalent addend binding.