The Synthesis of a Solubilized [11]Phenacene Derivative

Posted May 14th, 2010 at 2:31 pm.

Kim Mullane

Mentor: Dr. Frank Mallory

[n]Phenacenes are molecules containing n aromatic rings joined together in a zigzag pattern. Since they can be thought of as graphene ribbons, which have conductive properties, they should have the potential to be used as molecular wires. The solubility of unsubstituted [n]phenacenes decreases dramatically with increasing n; [7]phenacene was found by the Mallory group to have negligible solubility. Currently the longest known [n]phenacene is an [11]phenacene derivative that was synthesized by the Mallory group with tert-butyl substituents acting as solubilizing groups, but it was found to have only modest solubility. The goal of my research is the synthesis of the [11]phenacene derivative shown below. The purpose is to test whether the long-chain alkyl groups R can provide the necessary solubility to allow the synthesis of even larger [n]phenacenes with n = 15 and n = 19.

mullane

The planned 15-step route for the synthesis of this compound involves a sequence of different types of chemical reactions, including Grignard, Friedel-Crafts, bromination, Arbuzov, Horner-Wadsworth-Emmons, and photocyclization reactions.

Filed under: 2009,Mallory, Dr. Frank,Mullane, Kim by Ann Dixon

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