The Synthesis of an Alkyl-Solubilized [15]Phenacene

Posted July 10th, 2011 at 8:03 pm.

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.

ahall1

ahall2

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.

Filed under: 2011,Hall, Ariana,Mallory, Dr. Frank by Michelle Han

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