Palladium catalysed C–H arylation of pyrenes: access to a new class of exfoliating agents for water-based graphene dispersions. Issue 9 (30th January 2020)

• Record Type: Journal Article
• Authors: Just-Baringo, Xavier; Shin, Yuyoung; Panigrahi, Adyasha; Zarattini, Marco; Nagyte, Vaiva; Zhao, Ling; Kostarelos, Kostas; Casiraghi, Cinzia; Larrosa, Igor
• Is Part Of: Chemical science. Volume 11:Issue 9(2020)
• Page Start: 2472
• Page End: 2478
• Publication Date: 2020-01-30
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c9sc05101e
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Novel pyrene surfactants for aqueous graphene exfoliation were prepared via C–H arylation of pyrene-1-carboxylic acid. 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.