Unsubstituted azobenzene possesses a Z-isomer thermal half-life of ca. 2 days, while many of its derivatives possess Z-isomer half-lives on the order of hours or minutes. Bleger, Schwarz, Brouwer and Hecht reported that introducing ortho-fluorine atoms to the azobenzene core structure drastically increases the thermal stability of the Z-isomer. When an easily oxidized aryl amine “redox auxiliary” is attached to ortho-fluoro-azobenzene, a compound with an unusually long Z-isomer half-life is reported (t1/2 ~ 20 days). The addition of a catalytic amount of oxidant results in a thermal Z--&gt;E rate acceleration that yields catalytic and quantitative Z--&gt;E conversion upon mixing. The details of the photo-electro switching of this azobenzene will be reported.

Redox auxiliary mediated Z-->E switching of a stable cis azobenzene

255th National Meeting (2018)

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