9-Mesityl-10-phenylacridinium BF4

Technical Specifications

Product Description & Scientific Applications

Acridinium salts are metal-free organic photocatalysts for visible-light photoredox catalysis, and a sustainable alternative to the ruthenium and iridium polypyridyl complexes conventionally used for the same transformations. In the excited state the acridinium ion is among the most strongly oxidising organic photocatalysts available, with excited-state potentials frequently exceeding +2.0 V versus SCE.

The archetype is Fukuzumi’s 9-mesityl-10-methylacridinium ion, whose orthogonal design pairs a 9-mesityl electron donor with an acridinium electron acceptor to give a long-lived charge-transfer state on photoexcitation. Early acridiniums degraded by nucleophilic attack; an N-aryl substituent on the acridinium nitrogen, in place of N-alkyl, improves chemical stability.

On absorbing a visible photon these catalysts initiate radical cascades by single-electron transfer, driving anti-Markovnikov hydrofunctionalisation of alkenes and C–H functionalisations including Giese and Minisci reactions. They oxidise benzylic alcohols under oxygen by converting the arene to its radical cation, and construct C–N bonds from primary amines by direct C–H functionalisation of arenes under aerobic conditions. 9-Mesityl-10-phenylacridinium tetrafluoroborate is the N-phenyl member of that N-aryl series.

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