ORGN 780 |
| Shape-persistent macrocycles often undergo supramolecular self-aggregation, and their well-defined interiors lend themselves to host-guest interactions with small molecules of appropriate sizes and supramolecular association motifs. We have synthesized several arylene-imine macrocycles, and have examined their self-aggregation in various solvents by NMR spectroscopy. Unsubstituted phenylene-imine macrocycles do not exhibit significant aggregation in solution, while the unsubstituted naphthlenylene-imine macrocycles do undergo dimerization in THF with an association constant of 4x10-4M. We have also identified a 3:1 water:macrocycle complex and a 3:1 boric acid:macrocycle complex for the naphthylenylene macrocycles. The solution-state structures of these complexes have been determined by 1-D and 2-D NMR experiments, and x-ray crystal structures have also been obtained to further examine the supramolecular host-guest interactions. The effect of substitution on the phenylene rings on self- aggregation has also been examined.
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Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
