From Flat to Curved: Two-Dimensional Polymers and Circulene
AdvisorKING, BENJAMIN T.
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The focus of this dissertation is the synthetic efforts towards circulene and the synthesis of two-dimensional, hydrocarbon polymer.[n]Circulenes are an array of n-benzenoid rings surrounding a central n-sided polygon. Due to the curvature that can be induced by small (< 6 sided) or large (> 6 sided) central polygons, they can provide insight into the flexibility of aromatic systems. There have been numerous attempts to synthesize circulene, but it has not been synthesized so far. In an attempt to achieve this target, we designed a synthesis of octa-peri- benzocirculene. We succeeded in introducing six bonds but could not generate all eight bonds.Two-dimensional polymers (2DPs) are one-monomer unit thick, covalently bonded molecular sheets with a long-range periodic internal structure. A single layer of graphene is an example of a naturally occurring two-dimensional polymer. We have synthesized a two-dimensional, hydrocarbon polymer. The synthesis of our polymer is based on the solid-state photochemistry of the monomer, antrip. The key step of photopolymerization is the dimerization of anthracene blades at 9, 10 positions. Infrared spectroscopy and solid-state NMR spectroscopy establish the microstructure of the polymer.