Trace mild acid-catalysed Z → E isomerization of norbornene-fused stilbene derivatives: intelligent chiral molecular photoswitches with controllable self-recovery.

ABSTRACT: Stilbene derivatives have long been known to undergo "acid-catalyzed" Z → E isomerization, where a strong mineral acid at high concentration is practically necessary. Such severe reaction conditions often cause undesired by-reactions and limit their potential application. Herein, we present a trace mild acid-catalyzed Z → E isomerization found with stilbene derivatives fused with a norbornene moiety. By-reactions, such as the migration of the C[double bond, length as m-dash]C double bond and electrophilic addition reactions, were completely inhibited because of the ring strain caused by the fused norbornene component. Direct photolysis of the E isomers at selected wavelengths led to the E → Z photoisomerization of these stilbene derivatives

SUBMITTER: Hao T 

PROVIDER: S-EPMC8179340 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature