Control of stilbene conformation and fluorescence in self-assembled capsules
Journal
Beilstein Journal of Organic Chemistry
Journal Volume
5
Date Issued
2009
Author(s)
Ams, Mark R.
Ajami, Dariush
Craig, Stephen L.
Rebek, Julius, Jr.Ams, M. R.
Ajami, D.
Craig, S. L.
Rebek, J.
Abstract
The extensively studied trans-stilbene molecule is known to give only weak fluorescence in solution and inside loosely-fitting synthetic capsules. However, trans-stilbene has been recently studied in the context of antibody interiors, where binding results in strong blue fluorescence. The present research was undertaken to understand the spatial factors that influence stilbene fluorescence. trans-Stilbene was encapsulated in the snug, self-assembled complex 1.1 and exhibited fluorescence quenching due to the distortion of its ground-state geometry. When the complex is elongated by incorporating glycouril spacers, trans-stilbene is allowed to adapt a fully coplanar arrangement and fluorescence returns. © 2009 Ams et al; licensee Beilstein-Institut.
Type
journal article