ORGN 273 |
| The cyclization of hexamethylenetetramine with phloroglucinol derivatives affords the 1-aza-adamantanetrione donor-σ-acceptor core. Molecules functionalized with aryl amides readily aggregate in halogenated organic solvents to form gels at concentrations as low as 0.5 wt %. Characterization of the monomers and their assemblies by NMR and IR spectroscopy, X-ray diffraction, SEM, and computation will be discussed from which emerges a link between the self-assembly properties of the systems and through-bond interactions at the molecules' cores. The synthesis of new ester-functionalized molecules will be presented that appear as versatile precursors to amides and acids. The esters are additionally shown prerequisite for unique reaction chemistry at the core that includes a regio-/stereoselective carbonyl reduction and an acid-catalyzed fragmentation. Finally, the first crystal structure of the 1-aza-adamantanetrione scaffold has been obtained that shows structural features consistent with strong σ-coupled donor-acceptor interactions within the tricyclic framework.
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Molecular Recognition and Self-Assembly
8:00 AM-12:00 PM, Tuesday, 28 March 2006 Georgia World Congress Center -- C302, Oral
Division of Organic Chemistry |
