Cation Transport Using Antraquinone-Derived Lariat Ethers and Podands: The First Example of Electrochemically Switched ''On/Off'' Activation/Deactivation

Article abstract of DOI:10.1021/ja00189a011

Antraquinone undergoes one- and two-electron reduction to form either radical anions or dianions.When a crown-ather-type macrocycle or a polyethyleneoxy side chain is attached, the reduced aromatic and the oxygen donor groups cooperate to bind the cation.Binding of Li(1+) or Na(1+) is greater when antraquinone is reduced because there is a charge-charge intraction between it and the cation.This property has been used to facilitate transport.Thus, reduction at the source phase enhances cation binding, and oxidation in the receiving phase induces cation release.Activation/deactivation was effected electrochemically.The ligands studied in a bulk CH2Cl2 phase were 1-((9,10-dioxo-1-oxanthracenyl)methyl)-15-crown-5, 1; 1-((9,10-dioxo-1-oxanthracenyl)methyl)-18-crown-6, 2; 1-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)anthracene-9,10-dione, 3; 1-(2-(2-(2-(2-octadecyloxyethoxy)ethoxy)ethoxy)ethoxy)anthracene-9,10-dione, 4.The first example of an electrochemically activated (reduction) and deactivated (oxidation) cation transport system based on anthraquinone ligands is demonstrated.