In this Doctoral Thesis, through several examples of new chemical modifications characterized by high yields and selectivities and new supramolecular structures, held together by a wide range of intermolecular forces forming several new host systems, we reached our target to revamp triphenylene and derivatives as a new molecular scaffold in supramolecular chemistry. More specifically, the introduction in our triphenylenic scaffold of alkyl thiol chains allowed the formation of sulphide and disulphide covalent cages, while by insertion of pyridine moieties through Mannich reaction it was possible to obtain transition metal coordination cages upon addition of metal corners. The creation of a tris-acid from the original scaffold allowed the investigation of self-aggregation capsules through hydrogen bonds between carboxylic acids, and the functionalization with charged polytails attached to the central triphenylenic core, alternated with apolar substituents, allowed solubilization in water with the formation of very small micelles. Moreover, the interaction between positively charged and negatively charged triphenylenes permitted the creation of peculiar ionic hetero-dimeric capsules. We are sure that this will spur future investigation on the capsules and cages presented in this work, enriching the scientific community involved in this interdisciplinary field of research.
