Synthesis of Polyether-substituted [n]Phenacenes

Posted May 10th, 2010 at 1:32 pm.

Carrie Womack and Alessandra Samero

Mentor: Professor Frank Mallory

[n]Phenacenes are compounds consisting of a particular number (n) of benzene rings fused together as shown in the following example:


[6]phenacene; n=6

These compounds are potentially useful for electrical conductivity due to their conjugation. When n is sufficiently large, electron movement may be promoted via the large pi-systems. This assumption is based on the fact that [n]phenacenes are very similar in structure to the highly conductive graphite, a small section of which is pictured below.


[11]Phenacenes have been previously synthesized in the Mallory Lab, with tertiary butyl side chains attached to provide solubility. Because the resulting solubility was only barely adequate, the synthesis of phenacenes is currently being attempted with the more powerful solubilizing polyether side chains attached.

The goal for this project is to synthesize the [7]phenacene and the [15]phenacene, pictured below. The planned synthesis of these molecules involves a multi-step process using Horner-Emmons reactions, benzylic brominations, photocyclizations, and Arbuzov reactions.


[7] phenacene

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