Synthesis of Biomimetic Light-Driven E/Z Molecular Switches

Our work is devoted to the synthesis of new biomimetic molecular switches, capable to convert light-energy into a E/Z isomerization process. Computational studies performed on Rhodopsin have defined the penta-2,4-dieniminium cation as the minimal chromophore whose excited-state mimics the one of the natural pigment responsible of the vision mechanism. By embedding this π system into conformational rigid molecules we developed a new class of molecular switches featuring a selective and ultra-fast light-driven E/Z photoisomerization. An intriguing process, we named “cyclopropyl ring-opening/nitrilium ion ring-closing tandem reaction”, has been conveniently used to approach “one-pot” the pivotal chromophore. The successful functionalization of these molecules potentially allows their grafting to a peptide domain.