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

• Published in: Chemical science (Cambridge) Vol. 14; no. 35; pp. 9553 - 9559
• Main Authors: Bolotova, Iumzhana A, Ustyuzhanin, Alexander O, Sergeeva, Ekaterina S, Faizdrakhmanova, Anna A, Hai, Yu, Stepanov, Andrey V, Ushakov, Igor A, Lyssenko, Konstantin A, You, Lei, Lvov, Andrey G
• Format: Journal Article
• Language: English
• Published: Cambridge Royal Society of Chemistry 13-09-2023; The Royal Society of Chemistry
• Subjects: Aqueous solutions; Chemical reactions; Chemical synthesis; Chemistry; Photochemical reactions; Photochemistry
• ISSN: 2041-6520; 2041-6539
• DOI: 10.1039/d3sc02165c

There is incessant interest in the 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 or rearrangement) or reversible photocyclization (switching), depending on their structure. This finding paves a way towards wider application of diarylethenes in photopharmacology and bioinspired technologies that require aqueous media for photochemical reactions.
Potassium 2,3-diarylmaleates feature a full spectrum of photoactivity of diarylethenes in water, including irreversible oxidative cyclization and rearrangement as well as reversible photocyclization (switching).