Dedicated to Professor Bohdan Korybut-Daszkiewicz on the occasion of his 77th birthday. A number of novel tetracyano-substituted dihydrotetraaza[14] annulene (DH-TAA) analogues were obtained in a simple and convenient way by one-pot synthesis. The ligands, as well as their complexes with nickel(II), copper(II) and palladium(II) ions were characterised, including X ray structures for seven compounds. The X-ray analysis shows relatively short distances between tetraazamacrocyclic rings (3.0-3.3 Å), resulting from the presence of strong π-π interactions. Moreover, some of synthesised compounds can easily be modified in order to attach commonly used reactive groups, which makes them very promising as future components of π-interaction based supramolecular systems [a