We explore the possibility of designing and synthesizing molecules that could mimic the photoisomerization of the visual pigment Rhodopsin (Rh) including its low-temperature photochromism [1]. The retinal chromophore of Rh undergoes an efficient, ultrafast and stereoselective light-driven isomerization. In order to design a chromophore displaying a similar reactivity in common solvents we have been looking at diverse alkylated Schiff bases featuring a single isomerizable double bond. In this lecture we show that the indanylidene-pyrroline (NAIP) framework [2] provides a computationally and synthetically viable prototype for the development of systems that reproduce the excited state electronic structure and photoisomerization dynamics of Rh in methanol or water. We also show that, on the basis of these studies we have been able to achieve a system that, in perspective, can be used as electrostatic switch. This is an unprecedented �dipole� switch capable of inverting, reversibly, its ca. 15 D dipole moment upon photoisomerization [3].[1] Shapiro I. et al. (2011) J Am Chem Soc 133:3354-3364.[2] Sinicropi A. et al. (2008) Proc. Nat. Acad. Sci. USA  105:17642-17647.[3] Melloni A. et al. (2010) J Am Chem Soc 132:9310-9319.

From computational photobiology to the development of biomimetic molecular devices

242nd National Meeting (2011)

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