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A new difluoromethoxyl-containing acrylate monomer for PEG-b-PDFMOEA amphiphilic diblock copolymers

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Abstract

A new monomer, 2-(difluoromethoxy)ethyl acrylate (DFMOEA), was first synthesized from commercially available 2-hydroxyethyl acrylate via a one-step difluoromethylation reaction. A series of well-defined poly(2-(difluoromethoxy)ethyl acrylate) (PDFMOEA) homopolymers were prepared via atom transfer radical polymerization (ATRP) of DFMOEA initiated by 2-bromopropionate. The Mn of the obtained polymer increased linearly with the monomer conversion, and the dispersities were low throughout the polymerization (Mw/Mn < 1.20) though some bimolecular recombination and side reactions occurred during the polymerization. The glass transition temperature (Tg) of the homopolymers obtained by using differential scanning calorimeter (DSC) is about −44 °C, 9 °C higher than that of poly(2-methoxyethyl acrylate) (PMOEA) homopolymer, which indicated that the introduction of difluoromethoxyl is beneficial for increasing the Tg. ATRP of DFMOEA initiated by a PEG-based macroinitiator provided poly(ethylene glycol)-b-poly(2-(difluoromethoxy)ethyl acrylate) (PEG-b-PDFMOEA) amphiphilic diblock copolymers with low dispersities (Mw/Mn < 1.26). The critical micelle concentrations (cmc) of PEG-b-PDFMOEA amphiphilic diblock copolymers in aqueous solution were determined by fluorescence probe technique and the cmc values decrease gradually with the increase of the length of hydrophobic PDFMOEA segment. It was found that PEG-b-PDFMOEA amphiphilic block copolymers could self-assemble into spherical micelles with a diameter of around ca. 45 nm in aqueous media which were visualized by transmission electron microscopy (TEM).

Graphical abstract: A new difluoromethoxyl-containing acrylate monomer for PEG-b-PDFMOEA amphiphilic diblock copolymers

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Publication details

The article was received on 25 Jun 2018, accepted on 13 Sep 2018 and first published on 14 Sep 2018


Article type: Paper
DOI: 10.1039/C8PY00942B
Citation: Polym. Chem., 2018, Advance Article
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    A new difluoromethoxyl-containing acrylate monomer for PEG-b-PDFMOEA amphiphilic diblock copolymers

    H. Liu, G. Lu, C. Feng and X. Huang, Polym. Chem., 2018, Advance Article , DOI: 10.1039/C8PY00942B

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