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

Bisimine and bisamine AB(2) 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 AB(2) 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 10(9)–10(11) 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.