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; phenacene was found by the Mallory group to have negligible solubility. Currently the longest known [n]phenacene is an 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 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.
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.