Thesis advisor: Lawrence T. Scott / This dissertation describes the work that has been carried out towards accessing a C3v [6,6] nanotube end-cap through rational chemical synthesis. Continued advancement in carbon nanotube research has driven scientists to develop a successful route to usable quantities of nanotubes that are homogeneous in structure. Due to the current inability to separate nanotube mixtures efficiently, researchers in fields ranging from chemistry to computer science have been unable to exploit fully all that these unique molecules have to offer. Our envisioned approach to this obstacle involves elongation of a template endcap using iterative growth chemistry. The final stage of the proposed end-cap synthesis involves the execution of a six fold cyclodehydrogenation reaction. To carry out this desired transformation, a new microwave assisted variant of the anionic cyclodehydrogenation reaction has been developed. Through this chemistry we have been able to access a variety of both known and novel polycyclic aromatic hydrocarbons, often in impressively high yields. We hope that this chemistry will be useful to us in accessing the target nanotube end-caps, and to others in providing a new route to accessing a variety of polycyclic aromatic hydrocarbon cores. / Thesis (PhD) — Boston College, 2008. / Submitted to: Boston College. Graduate School of Arts and Sciences. / Discipline: Chemistry.