Bis(benzylamine) monomers: One-pot preparation and application in dendrimer scaffolds for removing pyrene from aqueous environments

Abstract

Bisimine and bisamine AB2 monomers have been synthesized from 3,5-diaminobenzoic acid and benzaldehyde derivatives without the need for protective groups or purification. This monomer preparation is universal for various electron-donating and electron-withdrawing benzaldehyde substrates. To demonstrate the versatility of these previously unreported AB2 monomers in the formation of high molecular weight structures, novel first-generation dendrimers and hybrid second-generation dendrimers have been synthesized. Using fluorescence spectroscopy, pyrene was shown to be removed from an aqueous environment upon exposure to thin dendrimer films, with the first-generation dendrimer removing 70% of the pyrene within 30 min and the hybrid second-generation dendrimers removing 38–52%. Inclusion formation constants were calculated to be on the order of 109–1011 M−1 and are comparable to the values of previously reported macromolecules. These results illustrate that size may not influence pyrene removal as effectively as composition.

Keywords

• amines
• dendrimer
• fluorescence studies
• imines
• pyrene