Supramolecular Coordination Complexes (SCCs) have been utilized in catalysis, biological systems and electrochemistry. The bottom-up approach to their syntheses, through directional metal-ligand bonding, allows for the design of nanoreactors with specific geometries. In addition, supramolecular chirality is of paramount importance in further understanding chiral molecular sensing and asymmetric catalysis. We will describe the synthesis and characterization of chiral enantiopure prismatic SCCs. The proposed prism is composed of 3 components: 1. Two tridentate ligands, 4,6-tris(4-pyridyl)-1,3,5-triazine (2) ligands, constituting the top and bottom faces of the prism; 2. Three ditopic imidazole based ligands (3) as the side edges of the prism; 3. Six square planar palladium(II) complexes (4). The syntheses and isolations of molecular bricks 3 and 4 are included in this work. Ditopic ligand 3 was synthesized via a copper-catalyzed coupling reaction of methylimidazole and a p-diiodobenzene. Enantiopure square-planar palladium(II) 4 was obtained by a two-step procedure. Enantiopure D3-symetric prism (1) was obtained via self-assembly of the synthesized molecular “bricks” in the presence of guests in H2O; and was characterized using NMR spectroscopy, circular dichroism, mass spectrometry, and titration by GC (FID).

Water-soluble three-dimensional enantiopure chiral prismatic ensembles

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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