Solubility and aggregation behavior of dendronized poly(p-benzamide)s

A series of Fréchet dendronized poly(p-benzamide)s have been synthesized. To attach the dendron-functionalities to the poly(p-benzamide) backbone, a propargyl side chain was introduced to p-aminobenzoic acid. Then, copper catalyzed azide-alkyne cycloaddition was used to click a first generation (G₁) respectively a second generation (G₂) Fréchet-dendron azide onto the amino acid monomer. The resulting amino acids were polymerized using triphenylphosphite to obtain a poorly organo-soluble G₁-dendronized polymer and a non-aggregating G₂-dendronized polymer showing good organo-solubility. Furthermore, a strictly alternating non-aggregating G₁-TEG-dendronized polymer with good organo-solubility was synthesized. The aggregation behavior of these polymers was investigated by dynamic light scattering.