Modeling, preparation, and characterization of a dipole moment switch driven by Z/E photoisomerization.
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
Alfonso
A
Dipartimento di Chimica, Università degli Studi di Siena, via Aldo Moro 2, I-53100 Siena, Italy.
Rossi Paccani
Riccardo
R
Donati
Donato
D
Zanirato
Vinicio
V
Sinicropi
Adalgisa
A
Parisi
Maria Laura
ML
Martin
Elena
E
Ryazantsev
Mikhail
M
Ding
Wan Jian
WJ
Frutos
Luis Manuel
LM
Basosi
Riccardo
R
Fusi
Stefania
S
Latterini
Loredana
L
Ferré
Nicolas
N
Olivucci
Massimo
M
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
D015335:Molecular Probes; D010446:Peptide Fragments; D012545:Schiff Bases; D014364:Tryptophan