One‐pot synthesis of hyperbranched polyamines based on novel amino glycidyl ether

Ahn, Gyunhyeok; Kweon, Songa; Yang, Chungmi; Hwang, Ji Eun; Kim, Kyuseok; Kim, Byeong Su

doi:10.1002/pola.28865

Cited by 10 publications

(6 citation statements)

References 28 publications

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“…Inspired by the advent of click chemistry, the azide functionality is regarded as a good candidate for the post-polymerization modification of polyethers due to its potential to undergo further modification by Cu-catalyzed azide–alkyne cycloaddition (CuAAC) or Staudinger reduction. As a part of our ongoing effort in the development of novel functional glycidyl ether monomer library, − herein, we introduce a series of new azide-functional glycidyl ether monomers, azidoethyl glycidyl ether (AEGE), azidobutyl glycidyl ether (ABGE), and azidohexyl glycidyl ether (AHGE) that can be polymerizable under organic superbase-catalyzed AROP conditions. The homopolymerization of each monomer was compared using in situ 1 H NMR kinetic study.…”

Section: Introductionmentioning

confidence: 99%

Anionic Polymerization of Azidoalkyl Glycidyl Ethers and Post-Polymerization Modification

et al. 2019

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Polyethers like poly(ethylene glycol) have been widely used for a variety of valuable applications, although their functionalization still poses challenges due to the absence of functional handles along the polymer backbone. Herein, a series of novel azide-functionalized glycidyl ether monomers are presented as a universal approach to synthesize functional polyethers by post-polymerization modification. Three azide-functionalized glycidyl ether monomers possessing different alkyl spacers (ethyl, butyl, and hexyl) were designed and synthesized by a simple two-step substitution reaction. Organic superbase-catalyzed anionic ring-opening polymerization can proceed under mild conditions compatible with an azide pendant group, affording wellcontrolled azide-functionalized polyethers with low dispersity (Đ < 1.2). The azide pendant groups on the resulting polymers were readily modified to a variety of functional groups via copper-catalyzed azide−alkyne cycloaddition reactions and Staudinger reduction. Furthermore, copolymerization of azidohexyl glycidyl ether with allyl glycidyl ether was demonstrated to provide an additional orthogonal functional handle. We anticipate that this work provides a new platform for the preparation of diverse functional polyethers.

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Section: Introductionmentioning

confidence: 99%

Anionic Polymerization of Azidoalkyl Glycidyl Ethers and Post-Polymerization Modification

et al. 2019

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“…We first prepared Boc-protected aminoethanol glycidyl ether monomer (BAG) to synthesize hyperbranched hPAG, based on hPG backbone. 22 Owing to the unique three-dimensional architecture of hyperbranched hPG, which comprises a polyether backbone with several hydroxyl functional groups and exhibits excellent biocompatibility, it has gained significant attention in biological and biomedical applications. The Boc-protected hPAG was prepared by anionic ring-opening multibranching polymerization using trimethylolpropane as an initiator in the presence of potassium methoxide ( Figure S1 ).…”

Section: Resultsmentioning

confidence: 99%

Singlet Oxygen Generation from Polyaminoglycerol by Spin-Flip-Based Electron Transfer

Nam

Hong

Lee

et al. 2022

JACS Au

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Reactive oxygen species have drawn attention owing to their strong oxidation ability. In particular, the singlet oxygen ( 1 O 2 ) produced by energy transfer is the predominant species for controlling oxidation reactions efficiently. However, conventional 1 O 2 generators, which rely on enhanced energy transfer, frequently suffer from poor solubility, low stability, and low biocompatibility. Herein, we introduce a hyperbranched aliphatic polyaminoglycerol (hPAG) as a 1 O 2 generator, which relies on spin-flip-based electron transfer. The coexistence of a lone pair electron on the nitrogen atom and a hydrogen-bonding donor (the protonated form of nitrogen and hydroxyl group) affords proximity between hPAG and O 2 . Subsequent direct electron transfer after photo-irradiation induces hPAG •+ -O 2 •– formation, and the following spin-flip process generates 1 O 2 . The spin-flip-based electron transfer pathway is analyzed by a series of photophysical, electrochemical, and computational studies. The 1 O 2 generator, hPAG, is successfully employed in photodynamic therapy and as an antimicrobial reagent.

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“…PEO-based hydrogels are particularly desirable for biomedical applications owing to their non-toxicity, low immunogenicity, and thus excellent biocompatibility. In synthetic approaches toward PEO-based polyethers, A blocks can be readily prepared by employing diverse functional monomers − or post-polymerization modifications. − In this context, the abundance of available epoxide monomers can provide a wide range of functionality that can be further modified to achieve the desired physical and chemical properties for targeted applications. ,,, Alternatively, post-polymerization modification can be an ideal strategy for evaluating various functional groups across a single polymer with an identical degree of polymerization and molecular weight distribution. ,− Moreover, post-polymerization modification provides the synthesis of polymers with pendant groups through bypassing the limitations of direct polymerization. In view of these benefits, the post-polymerization modification is receiving significant interest to produce well-defined polymers with tailorable properties.…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of Poly(ethylene oxide)-Based Self-Healable Dynamic Triblock Copolymer Hydrogels

et al. 2020

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Stimuli-responsive smart hydrogels have garnered considerable interest for their potential in biomedical applications. While widely utilized, little is known about the rheological and mechanical properties of the hydrogels with respect to the type of cross-linker in a systematic manner. In this study, we present a facile synthetic route toward ABA triblock copolymer hydrogels based on poly(ethylene oxide) (PEO). Two classes of hydrogels were prepared by employing the functional allyl glycidyl ether (AGE) monomer during the polymerization followed by the subsequent post-polymerization modification of prepared PAGE-b-PEO-b-PAGE via respective hydrogenation or thiol-ene reaction: (1) chemically cross-linked hydrogels responsive to redox stimuli and (2) physically cross-linked hydrogels responsive to temperature. A series of dynamic mechanical analyses revealed the relaxation dynamics of the associative A block. Most interestingly, the redox-responsive hydrogels demonstrated a highly tunable nature by introducing reducing and oxidizing agents, which provided the self-healing property and injectability. Together with superior biocompatibility, these smart hydrogels offer the prospect of advancing biomedical applications.

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One‐pot synthesis of hyperbranched polyamines based on novel amino glycidyl ether

Cited by 10 publications

References 28 publications

Anionic Polymerization of Azidoalkyl Glycidyl Ethers and Post-Polymerization Modification

Anionic Polymerization of Azidoalkyl Glycidyl Ethers and Post-Polymerization Modification

Singlet Oxygen Generation from Polyaminoglycerol by Spin-Flip-Based Electron Transfer

Facile Synthesis of Poly(ethylene oxide)-Based Self-Healable Dynamic Triblock Copolymer Hydrogels

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