Synthesis of substituted tri-aryl amines for use as electrocatalysts

CHED 336

L. Kraig Steffen, lsteffen@mail.fairfield.edu1, Andrea D. Pelle1, Jenna Koliani1, Michael Shinall1, and Albert J. Fry, afry@wesleyan.edu2. (1) Department of Chemistry, Fairfield University, Box 781, 1073 North Benson Road, Fairfield, CT 06824, (2) Department of Chemistry, Wesleyan University, Middletown, CT 06459
A series of substituted tri-aryl amines have been synthesized, purified, and characterized. Each contains at least one amino group that can be diazotized and attached to a carbon fiber electrode by methods already worked out for similar molecules. The amines are diazotized and attached directly to carbon electrodes for use as Chemically Modified Electrodes (CME's). These electrodes will be used as electrooxidative catalysts for the oxidation of a variety of compounds including thioethers, alcohols, and silanes. In theory, the use of CME's can reduce the need for toxic heavy metal oxidants, often yield greater selectivity in oxidations, and, since the oxidant is attached to an electrode and is regenerated upon reaction, allows for a more efficient work-up and reuse of the oxidant in subsequent reactions. The aryl amines' electrochemical properties have been investigated by cyclic voltammetry before and after their attachment to the electrode surface.