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 [15]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.