Online

Potter, Robert G.

Chemistry

2008

PhD

Polyaromatic hydrocarbons (PAH) are useful molecules for supramolecular assemblies and nanoscale electronics materials. Due to their high degree of symmetry and lack of heteroatoms characterization is fairly simple and calculated properties very closely match experimental values. By utilizing a controlled, stepwise synthesis, which enables the regioselective incorporation of solubilizing side chains and electron donating or withdrawing groups, we were able to access many novel PAHs of various shapes and sizes. Using an unprecedented asymmetric protected alcohol-benzyl bromide Collman coupling strategy we have accessed linear oligocyclopentadienones and oligophenylenes not accessible through current methodology. Monomers of these two classes were studied both spectroscopically and computationally in order to fully characterize their electronic structure and see how perturbation of the PAH scaffold affected their respective molecular orbitals.