Azobenzene compounds exist in two isomeric forms: a thermodynamically favored trans and a less stable, higher energy cis structure. Photo-stimulation can be used to reversibly change between the two isomers, and thus azobenzenes can be utilized as molecular switches. The photoisomerization and lifetime effects of linking two azobenzenes to the amine redox center of methoxyaniline forming 4-methoxy-N,N-bis(4-(4-methoxyphenyl)diazinyl)phenyl)aniline are investigated. This bis(azobenzene)aniline, BA, was synthesized by Buchwald-Hartwig Cross Coupling of 4-methoxyaniline and two equivalences of 1-(4-bromophenyl)-2-(4-methoxyphenyl)diazene. The photo-conversion to cis,trans and cis,cis BA forms will be presented as well as the thermal lifetimes of these species. Redox catalysis for fast and efficient cis-to-trans switching of both azo linkages will be reported.

Molecular switching of bis(azobenzene)aniline

255th National Meeting (2018)

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