Dataset Information

Aminooxy and Pyridyl Disulfide Telechelic Poly(Polyethylene Glycol Acrylate) by RAFT Polymerization.

ABSTRACT: An efficient method to synthesize telechelic, bio-reactive polymers is described. Homotelechelic polymers were synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization in one step by employing bifunctional chain transfer agents (CTAs). A bis-carboxylic acid CTA was coupled to N-BOC-aminooxy ethanol or pyridyl disulfide ethanol resulting in a bis-N-BOC-aminooxy CTA and a bis-pyridyl disulfide CTA, respectively. RAFT polymerization of polyethylene glycol (PEG) acrylate in the presence of both CTAs resulted in a series of polymers over a range of molecular weights (~8.4 kDa to 35.2 kDa; polydispersity indices, PDIs of 1.11 to 1.44) with retention of end-groups post-polymerization. The polymers were characterized by (1)H NMR spectroscopy and gel permeation chromatography (GPC). Conjugations of small molecules and peptides resulted in homotelechelic polymer conjugates.

SUBMITTER: Grover GN

PROVIDER: S-EPMC3956054 | biostudies-literature | 2012 Jun

REPOSITORIES: biostudies-literature

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Publications

Aminooxy and Pyridyl Disulfide Telechelic Poly(Polyethylene Glycol Acrylate) by RAFT Polymerization.

Grover Gregory N GN Lee Juneyoung J Matsumoto Nicholas M NM Maynard Heather D HD

Macromolecules 20120601 12

An efficient method to synthesize telechelic, bio-reactive polymers is described. Homotelechelic polymers were synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization in one step by employing bifunctional chain transfer agents (CTAs). A bis-carboxylic acid CTA was coupled to <i>N</i>-BOC-aminooxy ethanol or pyridyl disulfide ethanol resulting in a bis-<i>N</i>-BOC-aminooxy CTA and a bis-pyridyl disulfide CTA, respectively. RAFT polymerization of polyethylene glycol ...[more]

PMID: 24648600

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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).

Dataset Information

Aminooxy and Pyridyl Disulfide Telechelic Poly(Polyethylene Glycol Acrylate) by RAFT Polymerization.

Publications

Aminooxy and Pyridyl Disulfide Telechelic Poly(Polyethylene Glycol Acrylate) by RAFT Polymerization.

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