Extended [n]Phenacenes Synthesis Solubilized by Phenyl Substituents

Posted May 10th, 2010 at 9:49 am.

Alessandra Samero

Mentor: Dr. Frank Mallory

The term [n]phenacenes refers to compounds with n benzene rings fused in an extended zig-zag formation. Very long [n]phenacenes may be of potential use as electrically conducting “molecular wires.” In order to chemically synthesize such long [n]phenacenes, solubilizing groups must be attached to the [n]phenacene backbone to assist in dissolving these molecules into solutions. At present, the largest phenacene synthesized with phenyl substituents as solubilizing groups has n = 7 as shown below. This compound was made by Annie Butler, in the Mallory group using a multi-step synthesis involving Wittig reactions, lithiations of aryl bromides, formations of phosphonium salts, and photocyclizations. One of the goals of the current research is to extend these previous syntheses to produce a new target molecule with n = 11 as shown below. The planned synthesis for this new target molecule involves a multi-step process using reactions such as Wittig reactions, benzylic brominations, formylations, and photocyclizations.

Filed under: 2005,Mallory, Dr. Frank,Samero, Alessandra by Ann Dixon

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