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.
Highlights
During the last few years graphene has emerged as a revolutionary material attracting much attention due to its unique properties and multiple applications.[1]
A new and diverse family of pyrene derivatives was synthesised via palladium-catalysed C–H ortho-arylation of pyrene-1-carboxylic acid
A er screening of the reaction parameters,[18] both the 2-arylated pyrenecarboxylic acid 3a and the corresponding decarboxylated 2-arylpyrene 5a could be obtained in good yields (Table 1, entries 3a and 5a)
Summary
During the last few years graphene has emerged as a revolutionary material attracting much attention due to its unique properties and multiple applications.[1]. Palladium catalysed C–H arylation of pyrenes: access to a new class of exfoliating agents for water-based graphene dispersions†
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