The Synthesis of an Alkyl-Solubilized [15]Phenacene

Posted June 24th, 2010 at 4:03 pm.

Abstract: Kimberly Mullane
Mentor: Dr. 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. My previous attempted synthesis of an [11] phenacene with two long-chain alkyl groups proved difficult due to solubility issues. The purpose of my research this summer is to test whether four 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.

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: 2010,Mallory, Dr. Frank,Mullane, Kimberly Tags: by Lisa Klinman

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