I&EC 19 |
| Persubstituted phloroglucinols (i.e., derived from 1,3,5-trihydroxybenzene) are the centerpiece of two classes of functional molecules that will be discussed. In one, the C3-symmetrically disposed hydroxyl groups act as hydrogen bond donors to acceptor functionalities stationed in the 2,4,6-positions of the aromatic core. Six- or seven-membered ring H-bonding then stabilizes two limiting substituent conformations (anti and syn), of which the syn offers convergent recognition groups and a cup-like shape suitable for host—guest chemistry or cage construction. H-bonding and conformational aspects describing the scaffolds are probed by 1H NMR (in solution), X-ray crystallography, and molecular modeling. Cyclization of selected phloroglucinols with hexamethylenetetramine affords a second class of functional molecules, 1-aza-adamantanetriones. Similar intramolecular H-bonding both stabilizes a propeller-shaped conformation and facilitates self-assembly of the now donor-σ-acceptor molecules. Recent data concerning the unique electronic properties of these systems will be reported. |
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Molecular Containers, Sponsored by Separation Science and Technology Sub-Division
1:30 PM-5:15 PM, Sunday, 10 September 2006 Moscone Center -- Room 250, Oral
Division of Industrial & Engineering Chemistry |