Working on the Frontier of Aromatic Carbon Chemistry: A New Approach to the Synthesis of [n]Phenacenes

Posted May 10th, 2010 at 9:44 am.

Dustin Raup

Mentor: Dr. Frank Mallory

[n]Phenacenes are compounds comprised of n benzene rings fused together. A simple example is the [5]phenacene shown below.

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These compounds are meant to mimic the behavior of graphite sheets, which have an analogous fused ring structure. Because of the similarities in structure and arrangement between the [n]phenacenes and graphite, it is thought that very long [n]phenacene compounds would make excellent candidates for molecular wires due to the extensive conjugation in the pi-electrons which makes graphite such a good conductor of electricity.

[n]Phenacenes have been synthesized in lengths of up to eleven fused rings by members of Dr. Mallory’s research group. It has been found in those experiments that as these molecules grow large they grow increasingly insoluble; this is troubling because they must be in solution in order to be built upon. Thus, these compounds must have solublizing groups substituted along the molecule to maintain solubility at reasonable temperatures.

Several different multi-step synthesis schemes with various solublizing groups have been explored in past work by the Mallory group, but these schemes have not succeeded in building anything larger than the [11]phenacene size. Work has just begun on a new multistep scheme that has been designed with a [19]phenacene with ether (RO) solublizing groups as the end product; this product would be the first molecule of such great length ever produced in this family of compounds.

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Filed under: 2005,Mallory, Dr. Frank,Raup, Dustin by Ann Dixon

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