Chemistry Faculty Publications

Document Type

Article

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.

Publication Date

7-2010

Publication Title

Journal Of The American Chemical Society

Volume

132

Issue

27

Start Page No.

9310

End Page No.

9319

DOI

10.1021/ja906733q

Included in

Chemistry Commons

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