Non-cyclic formylated dipyrromethanes as phosphate anion receptors

Abstract

New tetrakis- and hexakis(1H-pyrrole-2-carbaldehyde) anion receptors are described. The anion binding properties of these receptors were studied in organic media and in the solid state. The receptors displayed good affinity for the dihydrogenphosphate and pyrophosphate anions (as the tetrabutylammonium salts) in chloroform even in the presence of a polar protic solvent, methanol. Solution phase spectroscopic analyses proved consistent with the binding mode seen in single crystal structural studies of the dihydrogenphosphate and pyrophosphate complexes and provided support for the contention that these receptors undergo conformational reorganization in order to accommodate the bound oxoanions both in chloroform solution and in the solid state.