Naphthalenetetracarboxydiimides and Related Compounds: Preparation and Characterization

Abstract

New 1,4,5,8-naphthalenetetracarboxydiimide (NDIM) derivatives were prepared in order to evaluate their solubities and binding properties to form dimers via hydrogen bonds. Di-tert-butylphenyl groups of NDIMs effectively disturbed their intermoleculater interaction even in high concentration and in low-polar solvent. The ¹H NMR titration studies in CDCl₃ indicated that all diimide derivatives did not exhibit the π-π stacking of naphthalene rings even in high concentration, and N-(2,5-di-tert-butylphenyl)-N′-hydrogen-1,4,5,8-naphthalenetetracarboxydiimide (2,5-BDIM), N-(3,5-di-tert-butylphenyl)-N′-hydrogen-1,4,5,8-naphthalenetetracarboxydiimide (3,5-BDIM), and N-(3,3-diphenylpropyl)-N′-hydrogen-1,4,5,8-naphthalenetetracarboxydiimide (3,3-PDIM) showed self-assembly properties through intermolecular hydrogen bondings.