Date of Award
Chemistry and Biochemistry
The purpose of this research was to explore the synthesis mechanisms of water-soluble ionic liquids with nitrogen-containing cationic bases for future use in transdermal drug delivery and forensic science applications. Ionic liquids are salts with an organic cation and either an organic or inorganic anion. They have asymmetric structures, which means that the molecules don’t pack together as neatly as other salts do, therefore, they don’t crystallize as easily, and their melting points are lower. Ionic liquids have melting points below 100°C, and many are liquid at room temperature. Mechanistic studies reveal that the potency of ILs in enhancing transdermal drug delivery correlates inversely with the inter-ionic interactions as determined by 2D 1H Nuclear Magnetic Resonance spectroscopy. After performing porcine skin test trials with choline trans-2-hexenoate and choline trans-2-octenoate, it was determined 2-octenoic acid was the best anionic candidate for further IL synthesis in regards to transport through porcine skin. Chemical interactions and organic processes and methods were used in the synthesis of seven new ionic liquids: (1:2) choline:3-pentenoate, (1:2) choline:trans-2-hexenoate, (1:2) choline:2-octenoate, (1:2) 1-methylimidazolium:2-octenoate, (1:2) 1-methylpyrrolidinium:2-octenoate, (1:2) pyridinium:2-octenoate, and (1:2) 4-methylmorpholinium:2-octenoate. Ionic liquids are of growing interest in the scientific community due to the vast range of physicochemical properties that can be accessed through specific tailoring of the cationic or anionic constituents of the ionic liquid. Choline-based ILs, specifically, have been used to enhance the transdermal delivery of several small and large molecules; however, research into different nitrogen-cationic containing ILs is significantly lacking in the literature. Overall, this research provides a generalized framework for optimizing ionic liquid synthesis for enhancing skin permeability in the hopes that transdermal delivery of drugs will be a viable, non-toxic, and noninvasive option for the future of medicine.
Galloway, Jo, "The Synthesis and Characterization of Ionic Liquids using Nitrogen-Based Cations for Transdermal Delivery" (2022). Honors Theses. 2474.
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