Synthesis of bis(quinoxalino) Ligand for the Removal of Transition Metal Contamination
Alexander J Farmer
Transition metal contamination is a constant concern both in the environment and in chemical reaction mixtures. One proposed solution, is the use of perazacrown macrocycles to selectively bind and remove transition metals. The aim of our project was to determine a novel synthesis of bis(quinoxalino) perazacrown macrocycles for use as ligands to bind to transition metals. Our synthesis makes use of protected diamines as opposed to other methods such as high dilution or the use of a metal template. In doing so, we made use of microwave irradiation in order to complete the reactions on a more efficient timescale. The primary challenge that our method encountered was the synthesis of the key intermediate molecule. This proved difficult given the changes in the electronics following the first substitution of protected amine. The synthesis of this molecule was the final product which we were able to produce. In future work, the diamines will be deprotected by catalytic hydrogenation and the resulting product reacted with a free quinoxalino unit. This will give us the synthesis of the final product. The synthesis would then be repeated with four different substituents on the quinoxalino rings and three different diamines on the perazacrown subunit, and the resulting molecules would be tested for transition metal binding properties.
Honors Thesis - Undergraduate
Primary Advisor's Department
Stander Symposium poster
"Synthesis of bis(quinoxalino) Ligand for the Removal of Transition Metal Contamination" (2017). Stander Symposium Posters. 1107.