. 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.

Public Health Relevance

. 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.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Postdoctoral Individual National Research Service Award (F32)
Project #
5F32GM120799-02
Application #
9327683
Study Section
Special Emphasis Panel (ZRG1)
Program Officer
Lees, Robert G
Project Start
2016-08-01
Project End
2018-06-30
Budget Start
2017-08-01
Budget End
2018-06-30
Support Year
2
Fiscal Year
2017
Total Cost
Indirect Cost
Name
University of California Berkeley
Department
Type
Graduate Schools
DUNS #
124726725
City
Berkeley
State
CA
Country
United States
Zip Code
94704
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