Novel Arylazo‐1, 2, 5‐oxadiazole Photoswitches: Synthesis, Photoisomerization and Nitric Oxide Releasing Properties. Issue 12 (1st September 2020)

• Record Type: Journal Article
• Authors: Zhilin, Egor S.; Polkovnichenko, Michael S.; Ananyev, Ivan V.; Fershtat, Leonid L.; Makhova, Nina N.
• Is Part Of: ChemPhotoChem. Volume 4:Issue 12(2020)
• Page Start: 5346
• Page End: 5354
• Publication Date: 2020-09-01
• Subjects: azo compounds -- nitric oxide donors -- photoswitches -- nitrogen heterocycles -- oxadiazoles; Photochemistry -- Periodicals; Periodicals; Electronic journals; 541.35
• DOI: 10.1002/cptc.202000157
• Languages: English
• ISSNs: 2367-0932

Abstract

Abstract: A series of novel molecular photoswitches incorporating an aryldiazenyl moiety linked to a 1, 2, 5‐oxadiazole (furazan) or 1, 2, 5‐oxadiazole 2‐oxide (furoxan) subunit was synthesized by a simple and step‐economic chemical route. Upon visible light irradiation, ( E )‐arylazo‐1, 2, 5‐oxadiazoles underwent photoisomerization to the corresponding ( Z )‐isomers which are stable under ambient conditions. Structural factors affecting the photoswitching ability were also revealed. Synthesized photoswitches exhibited good performance due to the absence of fatigue or decomposition over at least ten cycles under air in a temperature range of 20–60 °C. NO donor properties of the synthesized arylazofuroxans were also evaluated in vitro and it was found that ( Z )‐arylazofuroxans released significantly larger amounts of NO than the corresponding ( E )‐isomers, which suggests strong potential of these molecular photoswitches in photopharmacology and other biomedical applications. Abstract : Switch to more NO : A novel type of fatigue‐resistant molecular photoswitch based on the arylazo‐1, 2, 5‐oxadiazole structure was prepared. Visible‐light‐induced E / Z photoisomerization of arylazofuroxans resulted in enhanced NO‐donor properties indicating their strong potential in photopharmacology.