Date of Award


Document Type


Degree Name

Doctor of Philosophy (PhD)



First Advisor

Hughes, Thomas


Single walled carbon nanotubes (SWCNTs) have unique physical, optical and electronic properties. Current production methods provide SWCNTs as a polydisperse mixture, with respect to helicity, diameter and length, and cannot be tuned to yield a discrete SWCNT isomer. A bottom up approach would yield a single SWCNT, which would allow for a better understanding of how chemical modification affects a carbon nanotube’s properties. Synthesis by this route has yet to be accomplished. Phenylene ethynylene macrocycles were synthesized by a stepwise linear fashion and cyclooligomerization. These macrocycles are Diels-Alder cycloaddition precursors for a rational synthesis of a (9,0) SWCNT segment. Additionally, these macrocycles are of interest due to their highly conjugated two dimensional networks, which gives rise to high quantum efficiency. Therefore, the optical properties of these macrocycles were studied in several of solvents. In addition, a novel reductive imination was examined and used to synthesize a series of phenylene imine macrocycles. These systems could be precursors towards organic N-doped SWCNTs by either a hetro-Diels-Alder cycloaddition or pyrrole ring formation.