Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 27, Pages 9310-9319Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja906733q
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Funding
- Universita di Siena [PAR02/04]
- FIRB [RBAU01EPMR]
- CO-FIN2006 [200431072_002]
- Bowling Green State University
- School of Arts & Sciences of Bowling Green State University
- Ramon y Cajal [CTQ2009-07120]
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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.
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