title: A highly electron-deficient analogue of aniline, soluble oligomers, and their redox properties.
abstract: The synthesis and electrochemical oxidative coupling of a highly electron-deficient analogue of aniline results in the formation of soluble electron-deficient oligomers. Oligomers undergo related oxidation and reduction processes that are separated by a wide potential range. The mechanism behind this behavior is examined by cyclic voltammetry, optical absorption spectroscopy, (1)H NMR spectroscopy, and density functional theory calculations. Mesomeric isomerization of the oxidized oligomers leads to a very stable oxidized state that requires a large (2.8 V) overpotential to return to the neutral form.
authors: Lash Miller Chemical Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
authors: Brandon
authors: B
authors: Djukic
authors: Alan J
authors: AJ
authors: Lough
authors: Dwight S
authors: DS
authors: Seferos
mesh_terms: D000814:Aniline Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004583:Electrons; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012995:Solubility
chemical_list: D000814:Aniline Compounds; C023650:aniline