ORGN 200 |
| Two DNA base binding receptors 1 and 2 have been synthesized by three-step reactions, including Suzuki arylation of dihaloarenes, followed by metallization with n-butyl lithium and carboxylation with carbon dioxide. Crystals of the receptors were obtained from slow cooling of hot solution of the compounds in acetonitrile. The crystal structures of the compounds have been determined using X-ray crystallography. Both receptors form dimers through binding of one carboxylic group to the other. The structure of 1 shows that carboxylic group is in the same plane as the phenyl group; however, the pyrenyl group is perpendicular to the phenyl group. The structure of 2 shows that both carboxylic and pyrenyl groups are parallel to each other but perpendicular to the naphthyl group. The molecular recognition of DNA base 9-butyl adenine has also been carried out. The binding of 9-butyladenine by 1 results in the decrease of pyrene fluorescence intensity, but the binding of the 2 by 9-butyladenine results in increase of pyrene fluorescence.
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Total Synthesis, Materials, Devices and Switches, Molecular Recognition and Self-Assembly, Biologically-Related Molecules and Processes
8:00 PM-10:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |
