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; Paccani, Riccardo Rossi; Donati, Donato; Zanirato, Vinicio; Sinicropi, Adalgisa; Parisi, Maria Laura; Martin, Elena; Ryazantsev, Mikhail; Ding, Wan Jian; Frutos, Luis Manuel; Basosi, Riccardo; Fusi, Stefania; Latterini, Loredana; Ferre, Nicolas; and Olivucci, Massimo, "Modeling, Preparation, And Characterization Of A Dipole Moment Switch Driven By Z/e Photoisomerization" (2010). Chemistry Faculty Publications. 127.
Journal Of The American Chemical Society