title: Modeling, preparation, and characterization of a dipole moment switch driven by Z/E photoisomerization.
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.
authors.affiliation: Dipartimento di Chimica, Università degli Studi di Siena, via Aldo Moro 2, I-53100 Siena, Italy.
authors.forename: Alfonso
authors.initials: A
authors.lastname: Melloni
authors.forename: Riccardo
authors.initials: R
authors.lastname: Rossi Paccani
authors.forename: Donato
authors.initials: D
authors.lastname: Donati
authors.forename: Vinicio
authors.initials: V
authors.lastname: Zanirato
authors.forename: Adalgisa
authors.initials: A
authors.lastname: Sinicropi
authors.forename: Maria Laura
authors.initials: ML
authors.lastname: Parisi
authors.forename: Elena
authors.initials: E
authors.lastname: Martin
authors.forename: Mikhail
authors.initials: M
authors.lastname: Ryazantsev
authors.forename: Wan Jian
authors.initials: WJ
authors.lastname: Ding
authors.forename: Luis Manuel
authors.initials: LM
authors.lastname: Frutos
authors.forename: Riccardo
authors.initials: R
authors.lastname: Basosi
authors.forename: Stefania
authors.initials: S
authors.lastname: Fusi
authors.forename: Loredana
authors.initials: L
authors.lastname: Latterini
authors.forename: Nicolas
authors.initials: N
authors.lastname: Ferré
authors.forename: Massimo
authors.initials: M
authors.lastname: Olivucci
mesh_terms: D005453:Fluorescence; D007536:Isomerism; D008027:Light; D008958:Models, Molecular; D015335:Molecular Probes / Q000737:chemistry / Q000528:radiation effects*; D010446:Peptide Fragments / Q000737:chemistry* / Q000528:radiation effects; D055668:Photochemical Processes; D011487:Protein Conformation; D012545:Schiff Bases / Q000138:chemical synthesis* / Q000737:chemistry; D055672:Static Electricity; D014364:Tryptophan
chemical_list: D015335:Molecular Probes; D010446:Peptide Fragments; D012545:Schiff Bases; D014364:Tryptophan