Using Metal-Organic Frameworks to Separate Aryl Fluorides from Arenes

University Of California Berkeley, Berkeley CA

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Abstract

Project summary. Compounds containing a carbon-fluorine bond are abundant in active pharmaceutical drugs due to their desirable metabolic properties. However, isolating these types of compounds is often challenging because they are contaminated with closely related side products, such as the corresponding compounds containing a C?H bond, which are not readily separated from the desired product. This proposal aims to study the use of metal-organic frameworks, a relatively new class of solid porous materials that have been widely used for separations of gases, to separate fluorinated and non-fluorinated compounds based on their selective interactions with the framework. In order to identify which fundamental host-guest interactions are capable of separating these mixtures of products, we will study the ability of metal-organic frameworks bearing open metal sites and fluorinated linkers to preferentially bind aryl fluorides (with 4-fluorotoluene as a representative example) over arenes (with toluene as a representative example). The most successful materials identified will be further characterized by a variety of techniques to fully understand the mechanism of separation. If fruitful, these studies should lead to a generalizable solid adsorbent for the purification of biologically active (hetero)aryl fluorides.