Reaction of Copper(II) with N,N'–dimethyltribenzo– 1,4,7–triazacyclononatriene Favors Formation of Multiple Oxidation Products

Abstract

This study is an investigation of the macrocyclic CTV derivative N,N'-dimethyltribenzo-1,4,7- triazacyclononatriene and the results of its reaction with Copper(II) Bromide. This study builds upon previous studies which demonstrated that N,N'-dimethyltribenzo-1,4,7- triazacyclononatriene rearranges into the 5,9–dimethyl–5,9- dihydroquinoxalino–[3,2,1– de]phenazine cation radical species upon oxidation by Copper(II) followed by vapor diffusion recrystallization. This study continues in demonstrating that there are multiple products associated with the oxidation of N,N'-dimethyltribenzo-1,4,7- triazacyclononatriene, and that multiple variables, including stoichiometric ratio, solvent identity, and the number of methyl groups present on the macrocyle, directly affect the species which is produced.. This study primarily utilizes electronic absorption spectroscopy and infrared spectroscopy as identification tools of the products formed in solution. Each product gives a distinct spectrum, and has specific features in certain regions of the visible spectrum. Computational analysis was also performed to gives insight into the nature of the crystal structure of the cation radical species. This study allows us to conclude that the oxidation of N,N'- dimethyltribenzo-1,4,7-triazacyclononatriene is not a simple process and has multiple reaction pathways.