Structure and isomerization behavior relationships of new push–pull azo-pyrrole photoswitches

Abstract

A family of stilbenyl-azopyrroles compounds 2a–d and 3a–d was efficiently obtained via a Mizoroki–Heck C–C-type coupling reaction between 2-(4′-iodophenyl-azo)-N-methyl pyrrole (1a) and different vinyl precursors. The influence of the π-conjugated backbone and the effect of the pyrrole moiety were correlated with their optical properties. Studies via UV-Visible spectrophotometry revealed that the inclusion of EWG or EDG favors a red-shift of the main absorption band in these azo compounds compared with their non-substituted analogues. Furthermore, there is a clear influence between the half-life of the Z isomer formed by irradiation with white light and the push–pull behavior of the molecules. In several cases, the stilbenyl-azopyrroles led to the formation of J-type aggregates in binary MeOH : H₂O solvents, which are of interest for water compatible applications.