| Abstract
| - Protonated Schiff bases (PSBs) of polyenals constitute a class of light-driven switchers selectedby biological evolution that provide model compounds for the development of artificial light-driven moleculardevices or motors. In the present paper, our primary target is to show, through combined computationaland experimental studies, that it is possible to approach the design of artificial PSBs suitable for suchapplications. Below, we use the methods of computational photochemistry to design and characterize theprototype biomimetic molecular switchers 4-cyclopenten-2‘-enylidene-3,4-dihydro-2H-pyrrolinium and its5,5‘-dimethyl derivative both containing the penta-2,4-dieniminium chromophore. To find support for thepredicted behavior, we also report the photochemical reaction path of the synthetically accessible compound4-benzylidene-3,4-dihydro-2H-pyrrolinium. We show that the preparation and photochemical characterizationof this compound (together with three different N-methyl derivatives) provide both support for the predictedphotoisomerization mechanism and information on its sensitivity to the molecular environment.
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