Investigation of the Rearrangement of Organic Macrocycle N,N'-dimethyltribenzo-l ,4,7- triazacyclononane to 5,9-dimethyl-5,9- dihydroquinoxalino-[3,2, l-de]phenazine Cation Radical by Copper(II) Oxidation

Abstract

The goal of this project was to extend the results from previous studies, as well as produce and characterize the 5,9-dimethyl-5,9-dihydroquinoxalino-[3,2,l-de] phenazine cation radical formed by Ross Beattie (2010), as it was not previously reproducible. Infrared and electronic spectroscopy showed a confirmation in the formation of previous products by Nicholas Nutile (2012) and Caroline Foura (2013). Time studies were also reproduced as a confirmation of the formation of a nitrogen radical cation. The spectra for the solid state and recrystallization solution confirmed the product made by Beattie. X-ray crystallography data confirmed the formation of 5,9-dimethyl-5,9- dihydroquinoxalino-[3,2,l-de]phenazine cation radical in this study, therefore successfully reproducing the product made by Beattie. With those results, two different nitrogen radical cations were made throughout the process. Nutile and Foura saw one product, while Beattie produced the other. The first product seemed to be an intermediate that goes to the final product sometime during recrystallization. The recrystallization process had an unknown effect on the formation of 5,9-dimethyl-5,9- dihydroquinoxalino- [3,2,li-de]phenazine cation radical. The overall product through recrystallization matched that of Beattie's work, but a different product formed during the time studies.