Synthesis and solvent-controlled self-assembly of diketopiperazine-based polyamides from aspartame.

An aspartame-based AB-type diketopiperazine monomer, cyclo(l-aspartyl-4-amino-l-phenylalanyl) (ADKP), was synthesized and subsequently utilized in the polycondensation of homo-polyamides with high molecular weights. By using various amino acids, dicarboxylic acids, and diamines, random DKP-based copolymers were also synthesized. The self-assembly properties of ADKP and poly(cyclo(l-aspartyl-4-amino-l-phenylalanyl)) (PA1) were studied the solvent displacement method.

Morphology-Controlled Self-Assembly and Synthesis of Biopolyimide Particles from 4-Amino-l-phenylalanine.

Self-assembling polyimides (PIs) having diketopiperazine (DKP) components were synthesized by polycondensation of a 4-amino-l-phenylalanine (4APhe) dimer, an aromatic diamine newly designed in this study. The amino acid-derived PIs showed high thermal resistance, with a 10% weight loss temperature ( ) of 432 °C at the maximum, and did not show any glass transition below the thermal decomposition temperature. The poly(amic acid) (PAA) precursors formed nanospheres upon reprecipitation over dimethylacetamide into water.