Activation of Anthraquinone’s Electrophilicity by Light for a Dynamic C–O Bond

Abstract

Coupling of photoswitching with dynamic covalent chemistry enables control of the formation and cleavage of covalent bonds by light irradiation. peri -Aryloxyanthraquinones feature an exclusive ability to switch electrophilicity by interconversion between para - and ana -quinone isomers, which was used for the first time for the implementation of a dynamic C–O bond. Photogenerated ana -isomers undergo a concerted oxa -Michael addition of phenols to give hitherto unknown 4-hydroxy-10,10-diaryloxyanthracen-9-ones. These species were found to be in equilibrium with the corresponding ana -quinones, thus forming a dynamic covalent system of a new type. Withdrawal of the colored ana -quinones from the equilibria by visible light irradiation resulted in two para -quinones with “locked” aryloxy groups.