diarylethene

Diarylethene is the general name of a class of chemical compounds that have aromatic functional groups bonded to each end of a carbon–carbon double bond. The simplest example is stilbene, which has two geometric isomers, E and Z.

Under the influence of light, these compounds can generally perform two kinds of reversible isomerizations: E to Z isomerizations, most common for stilbenes (and azobenzenes). This process goes through an excited state energy minimum where the aromatic rings lie at 90° to each other. This conformation drops to the ground state and generally relaxes to trans and cis forms in a 1:1 ratio, thus the quantum yield for E-Z isomerization is very rarely greater than 0.5. 6π electrocyclizations of the Z form, leading to an additional bond between the two aryl functionalities and a disruption of the aromatic character of these groups. The quantum yield of this reaction is generally less than 0.1, and in most diarylethenes the close-ring form is thermally unstable, reverting to the cis-form in a matter of seconds or minutes under ambient conditions.