Saturday, October 27, 2007
Ballroom Posters (Greenville Hyatt Regency Hotel)
826

Synthesis of Methyl, N-Butyl and Iso-Butyl Diester Molecular Rectifiers

Aaron Blue, Jamila Broadway, Tiffany Fogg, and Darren L. Pearson. Fayetteville State University, Fayetteville, NC

Described in this research is the synthesis of three electron deficient organic molecular rectifiers. A rectifier is a device that allows for the conduction of electricity in only one direction. In the synthesis of the molecular rectifier, the central phenyl unit will have electron withdrawing ester groups attached. The attachment of the electron withdrawing groups will allow tuning of the organic molecule's highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy levels with metal electrodes. The ester groups will be formed by the oxidation of 1,4-dibromo-2,5-dimethylbenzene using nitric acid and potassium permanganate. The resulting carboxylic acids are then esterified using methyl, n-butyl and iso-butyl alcohol respectively. Once the esters are formed, the central phenyl unit will be coupled to terminal thioacetate endgroups using a Palladium/Copper cross-coupling reaction. The thioacetate endgroups will allow for the formation of Self-Assembled Monolayers onto gold surfaces once the acetate protecting groups are removed. The terminal thioacetate endgroup will be formed from the Sandmeyer reaction of 4-iodoaniline followed by the addition of sodium sulfide. The resulting disulfide is to be reduced with zinc metal in acetic acid. Finally the free thiol will be protected with acetyl chloride.