HYDROLYTIC PRODUCTS OF DIPHTHALIMIDODIETHYLAMINE AND TEMPERATURE INDEPENDENT SENSITIZED LUMINESCENCE OF THEIR LANTHANIDE(III) COMPLEXES

Syntheses and structural and luminescence studies of hydrolytic produc ts of diphthalimidodiethylamine (DPDA) and their lanthanide(III) compo unds have been undertaken in order to determine the potential for the phthalamate functionality to sensitize intense Eu3+ and Tb3+ emission via the (antenna effect). Acid promoted hydrolysis of the relatively s imple DPDA is efficient; hydrolysis is negligible at pH > 11. At pH 2- 3, hydrolysis to phthalic acid (1) occurs which upon interaction with DPDA yields the phthalic acid-DPDA supramolecular hydrate, DPDAH-HP . 1.75H(2)O. With a potassium carbonate-ethanol-acetonitrile mixture con taining a small amount of water, the novel phthalamate-phthalimide H2 . H2O is formed while at pH ca. 9-10 the new diphthalamate Na(2)3 . 3H (2)O is formed. These transformations have been formed by single cryst al X-ray analyses of DPDAH-HP . 1.75H(2)O and H2 . H2O. The crystal st ructures of DPDAH-HP . 1.75H(2)O and H2 . H2O reveal that the phthalam ates and phthalimides are stabilized by non-covalent (e.g. pi-pi stack ing and hydrogen bonding) interactions which are of interest as potent ial conduits for energy transfer and are responsible for molecular agg regations seen in FAB mass spectrometry of H2 . H2O and Na2(3). H2O. E uropium(III) compounds of 3(2-) and H2 exhibit intense sensitized red emission which is, surprisingly, temperature independent.