Jasmine Bordelon

Abstract:

Single-walled carbon nanotubes, sheets of polycyclic aromatic hydrocarbons rolled into cylinders, are materials with great potential for use in organic electronic devices, including organic photovoltaics. The current synthetic methods for carbon nanotubes require tedious purifications, and since the electronic properties depend on the structure of the tubes, the Hughes Research Group has planned a synthesis of monodisperse, single-structure tubes. This synthetic method requires the construction of monomers containing phenyl rings and acetylene building blocks which can then be strung together into rings. This summer I synthesized alkyl-substituted iodoalkyne monomers that can be subjected to Sonogashira cross-coupling reactions to create cyclotrimeric phenylene ethynylenes. The sequence of two halogenations of an alkylaniline followed by a deamination represents an alternative to the recent synthetic sequences developed by the Hughes Research Group. I scaled up these reactions to allow multiple attempts at reaching the latter stages of the macrocycle synthesis. I synthesized a bromoiodoarene, and then carried out two sequential palladium-catalyzed reactions on that arene to attach an alkyne and a second aromatic ring. I then converted the resulting biaryl compound into a terphenyl compound after converting its triazene to iodine and replacing that iodine with an aromatic ring.