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Synthesis of sequence-defined acrylate oligomers via photo-induced copper-mediated radical monomer insertions.

ABSTRACT: Photo-induced copper-mediated radical polymerization is used to synthesize monodisperse sequence defined acrylate oligomers via consecutive single unit monomer insertion reactions and intermediate purification of the compounds by column chromatography or preparative recycling size exclusion chromatography. Monomer conversions are followed during reaction by means of infrared spectroscopy. When reaction conditions are chosen carefully and any residues from chlorinated solvents are avoided, 100% pure Br end capped sequence defined oligomers are obtained, demonstrating the convenience and power of photo-induced copper mediated radical insertion for establishing sequence control. Within this work, a library of sequence defined oligomers containing polar and apolar ester groups have been obtained, and for the first time, perfectly monodisperse acrylate pentamers became accessible from radical insertion reactions.

SUBMITTER: Vandenbergh J

PROVIDER: S-EPMC5947509 | biostudies-literature | 2015 Oct

REPOSITORIES: biostudies-literature

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Synthesis of sequence-defined acrylate oligomers <i>via</i> photo-induced copper-mediated radical monomer insertions.

Vandenbergh Joke J Reekmans Gunter G Adriaensens Peter P Junkers Thomas T

Chemical science 20150703 10

Photo-induced copper-mediated radical polymerization is used to synthesize monodisperse sequence defined acrylate oligomers <i>via</i> consecutive single unit monomer insertion reactions and intermediate purification of the compounds by column chromatography or preparative recycling size exclusion chromatography. Monomer conversions are followed during reaction by means of infrared spectroscopy. When reaction conditions are chosen carefully and any residues from chlorinated solvents are avoided, ...[more]

PMID: 29861904

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Project description:The purpose of this work was to investigate the effect of multifunctionality on material properties of synthetic polymer aerogels. For this purpose, we present the synthesis and characterization of monolithic dendritic-type urethane-acrylate monomers based on an aliphatic/flexible (Desmodur N3300), or an aromatic/rigid (Desmodur RE) triisocyanate core. The terminal acrylate groups (three at the tip of each of the three branches, nine in total) were polymerized with 2,2'-azobis(isobutyronitrile) (AIBN) via free radical chemistry. The resulting wet-gels were dried with supercritical fluid (SCF) CO₂. Aerogels were characterized with ATR-FTIR and solid-state 13C NMR. The porous network was probed with N₂-sorption and scanning electron microscopy (SEM). The thermal stability of aerogels was studied with thermogravimetric analysis (TGA). Most aerogels were macroporous materials (porosity > 80%), with high thermal stability (up to 300 °C). Aerogels were softer at low monomer concentrations and more rigid at higher concentrations. The material properties were compared with those of analogous aerogels bearing only one acrylate moiety at the tip of each branch and the same cores, and with those of analogous aerogels bearing norbornene instead of acrylate moieties. The nine-terminal acrylate-based monomers of this study caused rapid decrease of the solubility of the growing polymer and made possible aerogels with much smaller particles and much higher surface areas. For the first time, aliphatic/flexible triisocyanate-based materials could be made with similar properties in terms of particle size and surface areas to their aromatic/rigid analogues. Finally, it was found that with monomers with a high number of crosslinkable groups, material properties are determined by multifunctionality and thus aerogels based on 9-acrylate- and 9-norbornene-terminated monomers were similar. Materials with aromatic cores are carbonizable with satisfactory yields (20⁻30% w/w) to mostly microporous materials (BET surface areas: 640⁻740 m² g-1; micropore surface areas: 360⁻430 m² g-1).

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Synthesis of sequence-defined acrylate oligomers via photo-induced copper-mediated radical monomer insertions.

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Synthesis of sequence-defined acrylate oligomers <i>via</i> photo-induced copper-mediated radical monomer insertions.

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Synthesis of sequence-defined acrylate oligomers via photo-induced copper-mediated radical monomer insertions.

Publications

Synthesis of sequence-defined acrylate oligomers &lt;i&gt;via&lt;/i&gt; photo-induced copper-mediated radical monomer insertions.

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OmicsDI is part of the ELIXIR infrastructure

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Synthesis of sequence-defined acrylate oligomers <i>via</i> photo-induced copper-mediated radical monomer insertions.