Synthesis of Fluorinated Fatty Acids for Use in Iron Oxide Nanoparticle Formation
Author:
Michaela Bracken ’22
Co-Authors:
Faculty Mentor(s):
Will Kerber, Chemistry Department
Funding Source:
Department of Chemistry
Abstract
Iron oxide nanoparticles are useful in several applications including imaging as contrast agents for MRI’s, drug carrier delivery for target specific sites and other biological therapeutic agents. Basic iron carboxylates of fatty acids can be used as precursors to nanoparticles. These complexes are important to study so that applications of iron oxide nanoparticles can be improved and built upon. If they contain a fluorine atom, basic iron carboxylates can be studied using 19F NMR to examine the structure and aggregation of these nanoparticle precursors. To accomplish this goal, fatty acids with a fluorine marker must be synthesized, due to their commercial unavailability. Our approach focused on an SN2-like fluorination of hydroxy fatty acids using XtalFluor-E. Sodium-12-fluorostearate was synthesized as an initial target from 12-hydroxystearic acid. This molecule was easily prepared but fell short of success due to the marker being too far away from the iron aggregation site. The position of the marker in the ligand is important and determines how well the activity can be monitored by NMR when reacted with iron. A second ligand, 6-hydroxy heptadecanoic acid, is being created that uses bromovaleric acid as the starting material. This synthesis, which is currently in progress, will require additional steps but will put the fluorine marker closer to iron to give a better read of the aggregation activity at the iron center.