Supramolecular self-assembly of a symmetric imine ligand functionalized with a dansyl fluorophore moiety

We report the synthesis and characterization of a symmetric [N₄] tetradentate imine-type ligand H₂L that incorporates a dansyl fluorophore group in both ligand arms. Two binding domains separated by a short arene spacer and two bulky arms with an anti conformation make this organic molecule suitable as precursor of metallosupramolecular species such as helicates. The molecular structure of H₂L has been analyzed by X-ray diffraction. This technique has revealed the formation of intermolecular hydrogen bond interactions that lead to the supramolecular self-assembly of ligand molecules in the solid state and the generation of oval-shaped channels in the 3D crystal packing.