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.
Melloni, A., Rossi Paccani, R., Donati, D., Zanirato, V., Sinicropi, A., Parisi, M.L., et al. (2010). Modeling, preparation and characterization of a dipole moment switch driven by Z/E photoisomerization. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 132(27), 9310-9319 [10.1021/ja906733q].
Modeling, preparation and characterization of a dipole moment switch driven by Z/E photoisomerization
Melloni, A.;DONATI, DONATO;SINICROPI, ADALGISA;BASOSI, RICCARDO;FUSI, STEFANIA;OLIVUCCI, MASSIMO
2010-01-01
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.File | Dimensione | Formato | |
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https://hdl.handle.net/11365/21495
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