Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/5856
Title: Modeling, preparation and characterization of a dipole moment switch driven by Z/E photoisomerization
Authors: Melloni, A.
Rossi Paccani, R.
Donati, Donato
Zanirato, V.
Sinicropi, Adalgisa 
Parisi, Maria Laura 
Martin, E.
Ryazantsev, M.
Ding, W. J.
Frutos, L. M.
Basosi, Riccardo 
Fusi, Stefania 
Latterini, L.
Ferrè, N.
Olivucci, Massimo 
Keywords: photochemical switches; quantum-mechanics/molecular-mechanics (QM/MM)
Issue Date: 2010
Project: None 
Journal: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Abstract: 
We report the results of a multidisciplinary research effort where the methods of computational photochemistry and retrosynthetic analysis/synthesis have contributed to the preparation of a novel N-alkylated indanylidene-pyrroline Schiff base featuring an exocyclic double bond and a permanent zwitterionic head. We show that, due to its large dipole moment and efficient photoisomerization, such a system may constitute the prototype of a novel generation of electrostatic switches achieving a reversible light-induced dipole moment change on the order of 30 D. The modeling of a peptide fragment incorporating the zwitterionic head into a conformationally rigid side chain shows that the switch can effectively modulate the fluorescence of a tryptophan probe.
Description: 
36441
URI: http://hdl.handle.net/20.500.12779/5856
ISSN: 0002-7863
DOI: 10.1021/ja906733q
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