Issue 48, 2020

Characterization of N-phenylmaleimide-terminated poly(ethylene glycol)s and their application to a tetra-arm poly(ethylene glycol) gel

Abstract

Tetra-arm poly(ethylene glycol) (TetraPEG) gels are tough materials whose toughness originates from their uniform network structure. They can be formed by combining the termini of tetra-arm polymers via chemical reactions with high conversion efficiency, such as the Michael addition, condensations using an active ester group, and alkyne–azide cycloadditions. Herein, we report the synthesis of a tetra-PEG gel using a tetra-arm polymer with N-phenylmaleimide moieties at the polymer ends (tetra-N-aryl MA PEG) as a scaffold. Tetra-N-aryl MA PEG can be obtained via a simple maleimidation using the modification agent p-maleimidophenyl isocyanate (PMPI), which directly transforms the hydroxy groups at the polymer ends into reactive N-aryl maleimide groups in a one-pot reaction. The thus-obtained tetra-N-aryl MA PEG was fully characterized using high-performance liquid chromatography (HPLC), matrix-assisted laser desorption ionization time of flight mass spectrometry, and proton nuclear magnetic resonance spectroscopy. HPLC analysis not only demonstrated the high purity of tetra-N-aryl MA PEG and the full conversion of the hydroxy groups, but also provided an effective characterization method for N-aryl maleimide-based PEG using a simple protocol, which enables us quantitative analysis of functionalized polymers with different N-aryl maleimide numbers. Furthermore, we fabricated a TetraPEG gel via Michael addition of the obtained tetra-N-aryl MA and thiol-terminated TetraPEGs. Thus, this report presents the application of tetra-N-aryl MA PEG as an effective precursor to obtain a uniform network structure and a method for its characterization; these results should provide support for the development of functional molecules, soft materials, and further functional materials based on the uniform-network-structure concept.

Graphical abstract: Characterization of N-phenylmaleimide-terminated poly(ethylene glycol)s and their application to a tetra-arm poly(ethylene glycol) gel

Supplementary files

Article information

Article type
Paper
Submitted
15 Sep 2020
Accepted
02 Nov 2020
First published
02 Nov 2020

Soft Matter, 2020,16, 10869-10875

Author version available

Characterization of N-phenylmaleimide-terminated poly(ethylene glycol)s and their application to a tetra-arm poly(ethylene glycol) gel

R. Takashima, M. Ohira, H. Yokochi, D. Aoki, X. Li and H. Otsuka, Soft Matter, 2020, 16, 10869 DOI: 10.1039/D0SM01658F

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements