Synthesis and properties of an anthraquinone-based redox switch for molecular electronics.

[reaction: see text] The synthesis of a molecular wire bearing an anthraquinone core and thioacetyl end groups for gold electrode binding is described. A model anthraquinone system, substituted with tert-butylthio groups, can be reversibly switched electrochemically from cross conjugated (low conductance "off") to linear conjugated (high conductance "on") via two-electron reduction/oxidation reactions. This feature holds promise for the anthraquinone-based wires to be used as redox-controlled switches in molecular electronic devices.