Publication Date

April 2018

Advisor(s)

Brian Northrop

Major

Chemistry

Language

English (United States)

Abstract

Covalent organic polygons (COPs) are supramolecular structures that are held together by dynamic and robust covalent bonds. Due to the dynamic reversibility of their assembly, COP syntheses can be optimized through changing reaction conditions to favor the formation of a single, specific product. Additionally, covalent organic polygons are assembled through reticular synthesis, meaning the size and geometry of the building blocks can be used to create structures with predetermined polyhedral shapes. Because COP architectures are assembled through covalent bonds rather than noncovalent interactions, they have high thermal and chemical stability. This high stability allows COPs to have important applications in catalysis. In addition to catalysis, covalent organic polygons have applications in gas storage, drug delivery, membranes, and as liquid crystalline materials. Of the many dynamic covalent reactions that can form polygons, the boronate ester forming reaction is specifically intriguing because of boron?s empty p orbital which can extend conjugation between neighboring aromatic systems. The research outlined in this thesis investigates the synthesis of two bis-boronic acids and two organic tetra-ols, with the aim of synthesizing four covalent organic polygons. Once assembled, the four supramolecular structures are anticipated to have remarkable applications across many fields of chemistry.

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