Tuning organogels and mesophases with phenanthroline ligands and their copper complexes by inter- to intramolecular hydrogen bonds

A novel family of highly functionalized molecules consisting of a central 4-methyl-3,5-diacylaminobenzene platform linked in close proximity to the methyl group by two lateral aromatic rings each equipped with two long alkoxy chains has been rationally designed. The presence of amide tethers and a chelating phenanthroline fragment connected via an ester dipole formed a new class of gelating reagents and mesomorphic materials. A few of these compounds have the tendency to form macromolecule-like aggregates through noncovalent interactions in hydrocarbon solvents and were found to exhibit thermotropic cubic mesophases. In light of the X-ray molecular structure of the methoxy ligand, an infinite network maintained by intermolecular hydrogen bonds as well as by π−π stacking of the phenyl subunits was evidenced. FT-IR studies confirm that the common driving force for aggregation in the organogels and microsegregation in the mesophase is the occurrence of a tight intermolecular H-bonded network that does not pe...