Activation of anthraquinone’s electrophilicity by light for a dynamic C-O bond

08 November 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Coupling of photoswitching with dynamic covalent chemistry enables the 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 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.


Dynamic covalent bond

Supplementary materials

Supporting Information
Full details of the experimental methods, NMR spectra, HRMS and UV−vis data, X-ray crystallographic data, and DFT calculations.


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