ORGN 304 |
| Christian Wolf, Xuefeng Mei, and Gilbert E. Tumambac. Department of Chemistry, Georgetown University, 37th and "O" Streets, Washington, DC 20057 |
| Axially chiral 1,8-diheteroarylnaphthalene N,N'-dioxides bearing cofacial pyridyl, quinolyl or acridyl rings display striking properties because of their unique geometry and related atropisomerism. As a consequence of their inherent fluorescence these rationally designed molecules can be used as stereoselective fluorosensors for mono- and bifunctional chiral compounds. Single crystal analysis revealed a sterically crowded structure forming a cleft with one-dimensional conformational flexibility. The chiral cleft of the sensor molecule is designed to accommodate substrates of varying size and to embed the analyte closely into its C2-symmetric framework. The high sensitivity inherent to fluorescence spectroscopy combined with the considerable stereoselectivity of this chemosensor affords a new tool for real-time enantioselective analysis. |
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Molecular Recognition and Materials
8:00 AM-12:00 PM, Tuesday, August 24, 2004 Pennsylvania Convention Center -- 201B, Oral
Division of Organic Chemistry |