Dual Sensing By Simple Heteroditopic Salt Receptors Containing an Anthraquinone Unit

Abstract

We synthesized simple ion pair receptors consisting of a crown ether cation binding site and an anthraquinone supported thiourea anion binding domain and studied their anion, cation and salt binding properties using spectroscopic, spectrophotometric and electrochemical measurements in acetonitrille solution. Apart from carboxylate anions, which cause deprotonation all the anions tested were found to associate with receptors more strongly in the presence of sodium cations, whereas in the presence of potassium or ammonium cation the anion binding strength was greatly diminished. A homotopic anion receptor lacking a crown ether unit, was unable to bind sodium salt more strongly than tetrabutylammonium salts. Solution and solid state X-ray measurements revealed that strong sodium coordination with the cation binding domain is responsible for the salt binding enhancement. Electrochemical measurements showed that the addition of anions to the ditopic ion pair receptors pretreated with sodium cations resulted in greater changes in reduction potentials compared to the addition of anions to receptors in the absence of Na+. Karbarz, M.; Romanski, J. Inorg. Chem. 2016, 55, 3616-3623. Figure 1