ORGN 713 |
| Tripodal 1,3,5-substituted 2,4,6-triethylbenzene scaffolds bearing three convergent H-bonding units are promising anion receptors. These receptors design utilizes a hexasubstituted benzene core with three functionalized arms and three ethyl arms in alternating arrangement that enforces a binding “cone” conformation. To improve the anion-binding ability and signaling response of these receptors we attach strong hydrogen bond donors, such as pyrrole-amide, bearing fluorescent (thio)urea labels onto the functional arms. The preorganized cone-like binding cavity comprises hydrogen bond donors for anion binding. The conformational behavior of the anion-binding arms was studied in solid state and in solution, and was correlated with the results of theoretical calculations. Interestingly, the limited conformational flexibility upon complexation of an anion prevents non-radiative relaxation of the fluorescent labels. This is reflected by increased sensor fluorescence upon anion binding. As a result these new sensors display turn-on fluorescence signaling, which is a very desirable feature in the sensor design.
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Asymmetric Reactions, Combinatorial Chemistry, Molecular Recognition and Self-Assembly, Proteins, Peptides, Amino Acids and Enzyme Inhibitors
8:00 PM-10:00 PM, Wednesday, March 28, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Organic Chemistry |
