Phthalimides: Supramolecular Interactions in Crystals, Hypersensitive Solution (1)H-NMR Dynamics and Energy Transfer to Europium(III) and Terbium(III) States

Detailed crystal structures and (1)H-NMR characteristics of some alkylamine-phthalimides, including dendritic polyphthalimides, are reported. These investigations were undertaken in order to obtain a better understanding of the relationship between solid-state supramolecular interactions, their persistence in solution and associated dynamics of magnetically hypersensitive phthalimide aromatic AA’BB’-AA’XX’ proton NMR resonances. Some alkylamine phthalimides feature folded molecular geometries, which we attribute to n-π interactions among proximal amine-phthalimide sites; those alkylamine-phthalimides that have no possibility for such interactions feature fully extended phthalimide functionalities. Accordingly, alkylamine phthalimide compounds with folded solid-state geometries feature solvent and temperature dependent hypersensitive AA’BB’-AA’XX’ (1)H-NMR line profiles, which we attribute to the n-π interactions. Luminescence of Eu(3+)((5)D(0)) and Tb(3+)((5)D(4)) states show well defined metal ion environments in their complexes with dendritic phthalimides, as well as relatively weak phthalimide-lanthanide(III) interactions.