Oxidative coupling of hydroxy- or aminoazobenzenes with secondary phosphine chalcogenides: Towards new media-responsive molecular switches |
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| Authors: | Pavel A Volkov Konstantin B Petrushenko Nina I Ivanova Kseniya O Khrapova Ludmila I Larina Nina K Gusarova Boris A Trofimov |
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| Institution: | A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation |
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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 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. |
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| Keywords: | Oxidative cross-coupling Phosphorylated azobenzene Synthesis Photoisomerization |
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