Issue 11, 2021, Issue in Progress

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

Abstract

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 via the solvent displacement method. Notably, PA1 self-assembled into particles with various morphologies in different solvent systems, such as irregular networks, ellipsoids, and hollow particles. The morphological transformation was also confirmed by dropping acetone and toluene onto the PA1 particles. Furthermore, infrared spectra and Hansen solubility parameters of PA1 and different solvents revealed the particle formation mechanism, which provided more insights into the relationship between the morphology and strength of the hydrogen bonding of each solvent.

Graphical abstract: Synthesis and solvent-controlled self-assembly of diketopiperazine-based polyamides from aspartame

Supplementary files

Article information

Article type
Paper
Submitted
30 Nov 2020
Accepted
28 Jan 2021
First published
03 Feb 2021
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2021,11, 5938-5946

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

H. Yin, K. Takada, A. Kumar, T. Hirayama and T. Kaneko, RSC Adv., 2021, 11, 5938 DOI: 10.1039/D0RA10086B

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