Biomimetic Light-Driven E/Z Switcher: Design and Syntesis

This thesis examines the design and synthesis of a new class of biomimetic switches that replicate different aspect of the Z/E photoisomerization of rhodopsin. Theoretical studies on rhodopsin showed that a penta-2,4-dieniminium moiety is the minimal structure responsible of the photochemical properties of the visual pigment. By trapping this π system into conformational rigid molecules we synthesized NAIP (N-alkylated indanylidene-pyrroline Schiff base) switches featuring a selective and ultra-fast light-driven E/Z photoisomerization. Computational and spectroscopic studies performed on the particular NAIPzw, have shown it constitutes the prototype of a novel generation of electrostatic switches potentially capable to influence the conformational state of macromolecular structures (as a protein). Our efforts are now directed towards the functionalization of this kind of system to create the specific molecular linkages on NAIP structure so as to allow its insertion in a peptide domain.