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.

Basosi, R., Busi, E., Elisei, F., Fusi, S., Latterini, L., Migani, A., et al. (2004). Design and photochemical characterization of a biomimetic light-driven Z/E switcher. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 126(30), 9349-9359 [10.1021/ja038859e].

Design and photochemical characterization of a biomimetic light-driven Z/E switcher

Basosi, Riccardo;Busi, Elena;Fusi, Stefania;Olivucci, Massimo;Ponticelli, Fabio;
2004-01-01

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.
2004
Basosi, R., Busi, E., Elisei, F., Fusi, S., Latterini, L., Migani, A., et al. (2004). Design and photochemical characterization of a biomimetic light-driven Z/E switcher. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 126(30), 9349-9359 [10.1021/ja038859e].
File in questo prodotto:
File Dimensione Formato  
JACS_04.pdf

non disponibili

Tipologia: Post-print
Licenza: NON PUBBLICO - Accesso privato/ristretto
Dimensione 249.62 kB
Formato Adobe PDF
249.62 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11365/32218
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo