The Synthesis of a [7]Phenacene Derivative as a Molecular Wire

Posted May 14th, 2010 at 2:24 pm.

Ariana Hall

Mentor: Dr. Frank Mallory

Phenacenes, or graphene ribbons, are molecules containing [n] aromatic rings joined in a zigzag pattern. Because pseudo one-dimensional graphene ribbons are similar to pseudo two-dimensional graphene sheets, they may have similar conductive properties, and so could be used as bridges for electron transport within molecules. Studies have previously been reported at Northwestern University using bridges made of benzene rings connected in the pattern shown below:


Unlike these bridges, where the rings are rotated at angles to one another, phenacenes are planar, and so may conduct electrons differently and possibly more effectively. This experiment will attempt to synthesize molecules with n=7 aromatic rings in the phenacene bridge. The phenacenes will have a bromine substituted on one end, and an amine substituted on the other end. They will also have a solubilizing alkyl group substituted on either end, as shown below:


The synthesis involves multiple reactions, including Grignard, Horner-Emmons, bromination and photocyclization reactions to build the molecules. If the phenacenes are successfully constructed, their conductive properties as bridges will be further studied.

Filed under: 2009,Hall, Ariana,Mallory, Dr. Frank by Ann Dixon

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