Molecular recognition of nucleosides, nucleotides and anionic planar substrates by a water-soluble bis-intercaland-type receptor molecule

The water-soluble macrocyclic bis-intercaland receptor molecule 1 has been prepared via the tetraimine 4 obtained by multiple amine–aldehyde condensation. It has been found to complex strongly planar anionic substrates such as aromatic carboxylates and nucleotides. The corresponding association constants in aqueous solution have been determined by 1H NMR and fluorescence measurements. The complexes present high stabilities and reveal interesting selectivities, in particular, among the nucleobases, with preferential binding of guanine-containing species.