Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/4925
Title: Design and photochemical characterization of a biomimetic light-driven Z/E switcher
Authors: Basosi, Riccardo 
Busi, Elena 
Elisei, F.
Fusi, Stefania 
Latterini, L.
Migani, A.
Olivucci, Massimo 
Pepi, A.
Ponticelli, Fabio
Sampedro Ruitz, D.
Zanirato, V.
Issue Date: 2004
Project: None 
Journal: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Abstract: 
Protonated Schiff bases (PSBs) of polyenals constitute a class of light-driven switchers selected by biological evolution that provide model compounds for the development of artificial light-driven molecular devices or motors. In the present paper, our primary target is to show, through combined computational and experimental studies, that it is possible to approach the design of artificial PSBs suitable for such applications. Below, we use the methods of computational photochemistry to design and characterize the prototype biomimetic molecular switchers 4-cyclopenten-2¢-enylidene-3,4-dihydro-2H-pyrrolinium and its 5,5¢-dimethyl derivative both containing the penta-2,4-dieniminium chromophore. To find support for the predicted behavior, we also report the photochemical reaction path of the synthetically accessible compound 4-benzylidene-3,4-dihydro-2H-pyrrolinium. We show that the preparation and photochemical characterization of this compound (together with three different N-methyl derivatives) provide both support for the predicted photoisomerization mechanism and information on its sensitivity to the molecular environment.
Description: 
35758
URI: http://hdl.handle.net/20.500.12779/4925
ISSN: 0002-7863
DOI: 10.1021/ja038859e
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