Issue 9, 2020

Palladium catalysed C–H arylation of pyrenes: access to a new class of exfoliating agents for water-based graphene dispersions

Abstract

A new and diverse family of pyrene derivatives was synthesised via palladium-catalysed C–H ortho-arylation of pyrene-1-carboxylic acid. The strategy affords easy access to a broad scope of 2-substituted and 1,2-disubstituted pyrenes. The C1-substituent can be easily transformed into carboxylic acid, iodide, alkynyl, aryl or alkyl functionalities. This approach gives access to arylated pyrene ammonium salts, which outperformed their non-arylated parent compound during aqueous Liquid Phase Exfoliation (LPE) of graphite and compare favourably to state-of-the-art sodium pyrene-1-sulfonate PS1. This allowed the production of concentrated and stable suspensions of graphene flakes in water.

Graphical abstract: Palladium catalysed C–H arylation of pyrenes: access to a new class of exfoliating agents for water-based graphene dispersions

Supplementary files

Article information

Article type
Edge Article
Submitted
09 Oct 2019
Accepted
23 Jan 2020
First published
28 Jan 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2020,11, 2472-2478

Palladium catalysed C–H arylation of pyrenes: access to a new class of exfoliating agents for water-based graphene dispersions

X. Just-Baringo, Y. Shin, A. Panigrahi, M. Zarattini, V. Nagyte, L. Zhao, K. Kostarelos, C. Casiraghi and I. Larrosa, Chem. Sci., 2020, 11, 2472 DOI: 10.1039/C9SC05101E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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