Photoisomerization of Tunable Esters Vinyl Sulfides

ADRIÁN A. HEREDIA; SILVIA SORIA CASTRO; GABRIELA OKSDATH MANSILLA; FABRICIO R. BISOGNO; LYDIA BOUCHET; CECILIA A. BARRIONUEVO; DANIEL A. CAMINOS; JUAN E. ARGÜELLO ; ALICIA B. PEÑÉÑORY

Foz do Iguacu

Conferencia; 12th Latin American Conference on Physical Organic Chemistry (CLAFQO-12); 2013

CLAFQO

Photo-switchable molecules are frequently employed in molecular rotors, sensors, host-guest chemistry and self-assembled systems, among other.1 Azobenzene is widely used due to tunability and solvent-related behavior among other properties.2 On the other hand, enol ester moiety enables the possibility of irreversibly disrupt the (Z)-(E)-isomerization by hydrolysis either in acidic or basic conditions. Since we have prepared a set of sulfur containing enol esters3 it becomes interesting as suitable scaffold for isomerization studies.4 Here, we show the (Z)-(E)-photoisomerization study of some enol esters in order to contribute to the understanding of their photochemistry. Photoinduced isomerization of enol ester is efficiently achieved under sensitization (acetone). Fragmentation may compete with isomerization depending on substituent attached to sulfur. Either H+ or HO- isomerization disruption of Z or E enol esters vinyl sulfides conduce to the corresponding ketone derivative.