Beauty in chemistry: Making artistic molecules with schiff bases

Abstract

In 1864, Hugo Schiff, aged 30, discovered the reaction of aromatic aldehydes with primary amines to give imine derivatives. A C=N imine bond presents the unique properties of being strong, as expected for a covalent double bond, and of being reversible due to a fast hydrolytic process. In view of such features, Schiff base condensations are thermodynamically controlled, which, in the case of reactions involving multifunctional aldehydes and primary amines, allow the formation of complex and sophisticated structures through a trial-and-error mechanism. Back hydrolysis can be prevented by hydrogenating C=N bonds under mild conditions. In such a way, stable rings and cages of varying sizes can be synthesized. Moreover, transition and post-transition metal ions, establishing coordinative interactions with imine nitrogen atoms, can address Schiff base condensations of even more complex molecular systems, whose structure is controlled by the geometrical preferences of the metal. Metal template Schiff base condensations have produced multinuclear metal complexes exhibiting the shape of tetrahedral containers, of double helices, and, supreme wonder, of the Borromean rings. These molecular objects cannot be compared to the masterpieces of painting and sculpture of the macroscopic world, but they instill in the viewer aesthetical pleasure and admiration for their creators.