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Issue 48, 2020
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Characterization of N-phenylmaleimide-terminated poly(ethylene glycol)s and their application to a tetra-arm poly(ethylene glycol) gel

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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

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Supplementary files

Article information


Submitted
15 Sep 2020
Accepted
02 Nov 2020
First published
02 Nov 2020

Soft Matter, 2020,16, 10869-10875
Article type
Paper

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

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