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|Title:||Modeling, preparation and characterization of a dipole moment switch driven by Z/E photoisomerization||Authors:||Melloni, A.
Rossi Paccani, R.
Parisi, Maria Laura
Ding, W. J.
Frutos, L. M.
|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.
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