The imidazole-containing N 4 -tetradentate ligand N-(2-(1H-imidazol-2-yl)-3-(pyridin-2-yl)propyl)-2,6-diisopropylaniline (L2 H ) and its N-benzyl-protected variant (L2 Bn ) at the imidazole fragment have been synthesized and fully characterized. Both molecules contain an unresolved C sp3 stereogenic center. The coordination behavior of the newly prepared ligands towards group IV metal ions (M IV = Zr, Hf ) has been examined through multinuclear 1 H and 13 C{ 1 H} NMR spectroscopy and selected single-crystal X-ray structural analyses. The ability of the imidazole fragment to enter the metal coordination sphere as a neutral or a monoanionic system has also been investigated, unveiling quite original coordination modes as well as unexpected molecular architectures. When one N imidazole atom is blocked by a benzyl protecting group (L2 Bn ), the ligand reaction with M IV (NMe 2 ) 4 (M IV = Zr, Hf ) as metal precursor gives rise to discrete monometallic tris(dimethylamido) 5-coordinated [a]