Cyclodextrin-based thiacavitands as building blocks for the construction of metallo-nanotubes

Two new cyclodextrin-based ligands with dual exo/endo binding domains were synthesised in high yields by reacting dimesylated or tetramesylated alpha-CD derivatives with sodium sulfide in either dimethylsulfoxyde or acetone/18-crown-6. The capping of adjacent glucose units was shown to be strongly favoured in both cases. Depending on the nature of the metal precursor being used, one of the synthesised thiacavitands forms either rigid nanotubular dimers or chelate complexes having receptor properties upon metal complexation.