From Flat to Curved: Two-Dimensional Polymers and [8]Circulene
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Authors
Bhola, Radha
Issue Date
2012
Type
Dissertation
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Keywords
aromaticity , circulene , two-dimensional polymers
Alternative Title
Abstract
The focus of this dissertation is the synthetic efforts towards [8]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 [8]circulene, but it has not been synthesized so far. In an attempt to achieve this target, we designed a synthesis of octa-peri- benzo[8]circulene. 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.
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In Copyright(All Rights Reserved)