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

Soft Matter
Rikito TakashimaHideyuki Otsuka

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 simp...Continue Reading

References

Nov 17, 2001·Chemical Reviews·K Y Lee, D J Mooney
Jan 5, 2002·Advanced Drug Delivery Reviews·Takashi MiyataKatsuhiko Nakamae
May 13, 2005·Nature·Cornelis StormPaul A Janmey
Oct 1, 2010·Advanced Materials·Brandon V SlaughterNicholas A Peppas
Feb 22, 2014·Science·Hiroyuki KamataTakamasa Sakai
May 18, 2016·The Journal of Physical Chemistry. B·Konstantinos KyriakosChristine M Papadakis

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Methods Mentioned

BETA
NMR
rheology
size-exclusion chromatography

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