Synthesis of (1,1-dimethyl)tridecyl-substituted [n]Phenacenes

Posted May 11th, 2010 at 2:34 pm.

Carrie Womack

Mentor: Professor Frank B. Mallory

[n]Phenacenes are compounds consisting of a particular number (n) of benzene rings fused together in a zigzag pattern. They are the one-dimensional analogs of the two-dimensional, highly conductive graphite, and the structural similarity of the two suggests that [n]phenacenes, often referred to as “graphite ribbons”, may have similar electrical properties.

[n]Phenacenes have been previously synthesized in the Mallory Lab with a variety of side-chains to provide solubility. While these side-chains have been sufficient for [n]phenacenes with n as high as 11, they do not appear to be adequate for larger values of n. In order to provide greater solubility, a critical property for these compounds, a new synthesis scheme is currently being attempted with a hydrocarbon side-chain consisting of 15 carbons instead of the 4-7 carbons that have been previously used.

The short-term goal for this project is to synthesize the [3]phenacene and the [7]phenacene derivatives, pictured below. It is proposed that this can be achieved through a multi-step synthesis involving Grignard reactions, Friedel-Crafts alkylations, ring brominations, benzylic brominations, Horner-Emmons reactions and photocyclizations. If the synthesis is successful, it will be extended to larger values of n.

womack_phenacenes

Filed under: 2007,Mallory, Dr. Frank,Womack, Carrie by Ann Dixon

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