Doctor of Philosophy (PhD)
Previous studies of [n]phenacenes utilized phenyl, and t-butyl solubilizing groups. However, it was shown that these substituents were not effective for solubilizing large [n]phenacenes with n greater than 11. Therefore, a new solubilizing group had to be used. A family of [n]phenacenes with polyether solubilizing groups has been synthesized using two separate divergent-convergent synthetic schemes. The central reaction vital to the synthesis is the ultraviolet light induced photocyclization, which allows for elongation of the phenacene chain. Unfortunately, the incorporation of the ether side chain had the unwanted effect of altering some of the key synthetic steps initially used to elongate the phenacene chains. Optimization of the synthetic pathway and solubility problems were two challenges that were necessary to overcome in order to synthesize the new molecules.
Bohen, Alyssa. "Synthesis of a Family of Polyether-Substituted Phenacenes." Ph.D. diss., Bryn Mawr College, 2013.