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Abstract One or two chalcogenophosphinate groups were introduced to the azobenzene scaffold via the oxidative cross-coupling reaction of 4-amino-, 4-hydroxy- and 4,4′-dihydroxyazobenzenes with secondary phosphine chalcogenides using the CCl4/Et3N system… Click to show full abstract
Abstract One or two chalcogenophosphinate groups were introduced to the azobenzene scaffold via the oxidative cross-coupling reaction of 4-amino-, 4-hydroxy- and 4,4′-dihydroxyazobenzenes with secondary phosphine chalcogenides using the CCl4/Et3N system under mild conditions in 41–95% yield. Cis-trans photoisomerization of the phosphorylated azobenzenes was reversibly controlled by alternating UV/Vis light irradiation. The chalcogenophosphinate group imparts the properties of media-responsive molecular photoswitches to the synthesized azobenzenes.
Journal Title: Tetrahedron Letters
Year Published: 2017
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