Abstract: Ariana Hall
Mentor: Dr. Frank Mallory
[n]Phenacenes, or graphene ribbons, are molecules containing [n] aromatic rings fused in a zigzag pattern. Pseudo one-dimensional graphene ribbons are similar to pseudo two-dimensional graphene sheets, so they may have similar conductive properties; because of this, they could potentially be used as molecular-scale wires. The Mallory group synthesizes phenacenes using the photocyclization of stilbene-like compounds under ultraviolet light. The longest [n]phenacene synthesized by the Mallory group had eleven rings. This experiment will attempt to synthesize the phenacene shown below in order to study the conductive properties of longer phenacenes.
Because longer [n]phenacenes are very insoluble, four solubilizing alkyl groups are attached to the molecule. The synthetic scheme involves Grignard, Friedel-Crafts, bromination, Horner-Emmons and photocyclization reactions.