Supramolecular dendritic π-conjugated systems:synthesis of glycinylurea functionalized π-conjugated diphenylanthracene guests and their complexation with dendritic hosts. Part I

Abstract

Glycinylurea functionalized π-conjugated diphenylanthracene guests (DPA guests) that bind to adamantyl urea modified dendritic hosts were synthesized and fully characterized by NMR spectroscopy (1H-NMR, 13C-NMR) and MALDI-TOF-MS. The resulting supramolecular assemblies have been investigated with respect to their binding properties. DPA guests molecules were able to click into urea functionalized N,N-bis[(3-adamantyl ureido) propyl] methyl amine host as a result of acid-base (between COOH of the guest and amines of the host) and hydrogen bonding interactions (between the urea linkages of dendrimer and the guest). The guest molecules were bound as 1:1 inclusion complexes and the association constants for both guests have been calculated. Subsequently, an adamantyl urea modified fifth generation poly(propylene imine) dendrimer was synthesized as a multivalent host which contains 32 N,Nbis[(3-adamantyl ureido) propyl] amine binding sites. Size exclusion chromatography showed that 32 of the DPA guests strongly bind to the fifth generation adamantyl functionalized dendritic host.</p