2,3-Diarylmaleate salts as a versatile class of diarylethenes with a full spectrum of photoactivity in water

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

Abstract

There is an incessant interest in transfer of common chemical processes from organic solvents to water, which is vital for the development of bioinspired and green chemical technologies. Diarylethenes feature a rich photochemistry, including both irreversible and reversible reactions that are in demand in organic synthesis, materials chemistry, and photopharmacology. Herein, we introduce the first versatile class of diarylethenes, namely, potassium 2,3-diarylmaleates (DAMs), that show excellent solubility in water. DAMs obtained from highly available precursors feature a full spectrum of photoactivity in water and undergo irreversible reactions (oxidative cyclization to phenanthrenes or rearrangement) or reversible photocyclization (switching), depending on their structure. This finding paves a way towards wider application of DAEs in photopharmacology and bioinspired technologies that require aqueous media for photochemical reactions.

Keywords

Diarylethene
Photoswitching
Photoreaction
Solubility in water
Photorearrangement

Supplementary materials

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Description
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Supporting Information
Description
Experimental procedures for the synthesis of DAM salts, NMR and absorbance spectroscopy data, mass spectra, X-ray crystallography, DFT calculations
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