ORGN 25 |
| The synthesis, derivatization, physical and molecular recognition properties of naphthalene diacid 1 are presented. Due to a restricted rotation associated with 1, atropisomeric properties are evident, enabling both the syn and anti isomers to exist independently. These isomers can be readily isolated in good yields by column chromatography. A temperature controlled NMR equilibrium study allowed the rotational barrier, &DeltaG, to be calculated. Host-guest interactions due to hydrogen bonding have identified 1 as a selective molecular receptor. Only guests containing hydrogen bonding moieties interacted with 1. The extent of this interaction was measured via NMR titration studies which showed a shift with the syn isomer only, suggesting that to bind to a guest two point of interaction are necessary. Based on the results of host guest study an appropriate guest was identified as being a good candidate for conducting a repeated cycle of writing, saving and erasing. In addition, diacid 1 is readily derivatized through the acid chloride to a series of amides.
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Molecular Recognition and Self-Assembly
8:00 AM-12:00 PM, Sunday, 28 August 2005 Washington DC Convention Center -- 201, Oral
Division of Organic Chemistry |
