Photoisomerization of tunable enol esters vinil sulfides

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

Foz do Iguazu

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

Universidad de Florianopolis

Photo-switchable molecules play a paramount role in the development of molecular rotors, sensors, host-guest chemistry and self-assembled systems, among other.1 Perhaps one of the most employed photoisomerizable chemical entity is azobenzene, due to its negligible photoinstability and tunable properties such as isomerization wavelength, solvent-related behavior and relatively simple functional group introduction.2 On the other hand, enol ester moiety provides the system with the possibility of irreversibly disrupt the (Z)-(E)-isomerization by ester hydrolysis promoted either by highly acidic or basic conditions. Recently, we have developed a robust and versatile protocol for the preparation of vinyl sulfides enol esters with different substitution pattern and noticed a remarkable resistance toward air and aqueous environments, making them a suitable scaffold for isomerization studies.3 The aim of the present work has been to explore the (Z)-(E)-photoisomerization of some vinyl sulfides enol esters in order to provide alternative opportunities to azobenzene photochemistry. Besides, the additional control by chemical stimuli such as pH for the ester cleavage, offers the possibility of disabling isomerization at both possible configurations. __________________ 1W. R. Browne, B. L. Feringa, Annu. Rev. Phys. Chem., 2009. 60, 407. 2H. M. D. Bandarab, S. C. Burdette, Chem. Soc. Rev., 2012, 41, 1809 3A. B. Peñéñory, J. E. Argüello, G. Oksdath Mansilla, S. Soria Castro, D. A. Caminos, C. A. Barrionuevo, L. Bouchet, A. A. Heredia, F. R. Bisogno; submitted for publication.