. 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.
. Fluorinated compounds are widely found in the pharmaceutical industry due to their desirable metabolic properties, but their purification can be difficult. This proposal aims to develop new solid materials that will aid in purifying these compounds, which will increase drug researcher's access to them.
McGuirk, C Michael; Siegelman, Rebecca L; Drisdell, Walter S et al. (2018) Cooperative adsorption of carbon disulfide in diamine-appended metal-organic frameworks. Nat Commun 9:5133 |
Milner, Phillip J; Martell, Jeffrey D; Siegelman, Rebecca L et al. (2018) Overcoming double-step CO2 adsorption and minimizing water co-adsorption in bulky diamine-appended variants of Mg2(dobpdc). Chem Sci 9:160-174 |
Milner, Phillip J; Siegelman, Rebecca L; Forse, Alexander C et al. (2017) A Diaminopropane-Appended Metal-Organic Framework Enabling Efficient CO2 Capture from Coal Flue Gas via a Mixed Adsorption Mechanism. J Am Chem Soc 139:13541-13553 |