Tuning the Electrochemical Redox Potentials of Catechol with Boronic Acid Derivatives.

A strategy to control the oxidation potential of catechol using borinic acids is presented. Borinic acids reversibly bind catechol to form boron "ate" complexes (BACs) that alter the electron density on the oxygen atoms of catechol and, in turn, the propensity of the catechol toward electrochemical oxidation. The effect of different substituents on the borinic acid are investigated to determine their efficacy in tuning the electron density within the BAC and the resulting oxidation potential.