Controlling the Assembly of C2-Symmetric Molecular Tectons Using a Thiocarbamate Appended Carbocyclic Cleft Molecule Analogous to Tröger’s Base

By way of appending the C2-symmetric carbocyclic cleft diol with thiocarbamates with varying substituents, significant control of the hydrogen bonded network can be achieved. Smaller alkyl substituents lead to the formation of stacked columns of components with the apex of one molecule suitably aligned in the cleft of a second. Aryl substituents, however, lead to the formation of ribbons via an H-bonding network. Additionally, the packing of these ribbons into networks is considerably different between the enantiopure and racemic clefts, with the latter giving rise to channels within the crystal structure.