(1‐Adamantyl)methyl Glycidyl Ether: A Versatile Building Block for Living Polymerization

Moers, Christian; Wrazidlo, Robert; Natalello, Adrian; Netz, Isabelle; Mondeshki, Mihail; Frey, Holger

doi:10.1002/marc.201400017

Cited by 9 publications

(7 citation statements)

References 77 publications

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“…Adamantyl glycidyl ether (AdaGE) is a promising epoxide monomer to create polyethers that can be used for the formation of supramolecular polymer architectures. Frey et al described the copolymerization of AdaGE with EEGE . Furthermore, the authors investigated thermal properties and inclusion complex formation with β-cyclodextrin, resulting in supramolecular grafting …”

Section: Poly(alkylene Oxide) Structures: Innovative Polyether Struct...mentioning

confidence: 99%

“…Frey et al described the copolymerization of AdaGE with EEGE. 300 Furthermore, the authors investigated thermal properties and inclusion complex formation with β-cyclodextrin, resulting in supramolecular grafting. 301 Catechol functionalities are prominent for their outstanding complexation and adhesion on a large variety of surfaces.…”

Section: Chemical Reviewsmentioning

confidence: 99%

“…84,85 Many of the recently reported PEG-copolymers show temperature dependent aqueous solubility and a cloud point. 97,99,144,275,277,292,300 This thermoresponsive behavior can be investigated by turbidity measurements. biomedicine.…”

Section: Chemical Reviewsmentioning

confidence: 99%

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Polymerization of Ethylene Oxide, Propylene Oxide, and Other Alkylene Oxides: Synthesis, Novel Polymer Architectures, and Bioconjugation

et al. 2015

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The review summarizes current trends and developments in the polymerization of alkylene oxides in the last two decades since 1995, with a particular focus on the most important epoxide monomers ethylene oxide (EO), propylene oxide (PO), and butylene oxide (BO). Classical synthetic pathways, i.e., anionic polymerization, coordination polymerization, and cationic polymerization of epoxides (oxiranes), are briefly reviewed. The main focus of the review lies on more recent and in some cases metal-free methods for epoxide polymerization, i.e., the activated monomer strategy, the use of organocatalysts, such as N-heterocyclic carbenes (NHCs) and N-heterocyclic olefins (NHOs) as well as phosphazene bases. In addition, the commercially relevant double-metal cyanide (DMC) catalyst systems are discussed. Besides the synthetic progress, new types of multifunctional linear PEG (mf-PEG) and PPO structures accessible by copolymerization of EO or PO with functional epoxide comonomers are presented as well as complex branched, hyperbranched, and dendrimer like polyethers. Amphiphilic block copolymers based on PEO and PPO (Poloxamers and Pluronics) and advances in the area of PEGylation as the most important bioconjugation strategy are also summarized. With the ever growing toolbox for epoxide polymerization, a "polyether universe" may be envisaged that in its structural diversity parallels the immense variety of structural options available for polymers based on vinyl monomers with a purely carbon-based backbone.

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Section: Poly(alkylene Oxide) Structures: Innovative Polyether Struct...mentioning

confidence: 99%

Section: Chemical Reviewsmentioning

confidence: 99%

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Polymerization of Ethylene Oxide, Propylene Oxide, and Other Alkylene Oxides: Synthesis, Novel Polymer Architectures, and Bioconjugation

et al. 2015

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“…To make the thermoresponsive polymer have a better application value, it is usually required that the polymer be equipped with an adjustable transition temperature in a wider temperature range. As has been established, linear thermoresponsive glycerol-polyethers can be excellent candidates due to their good biocompatibility and adjustability [32,33]. Poly(glycidyl ether)s, based on glycidyl methyl ether (GME) [34], ethoxyethyl glycidyl ether (EEGE) [35], and ethyl glycidyl ether (EGE) [35,36] exhibit thermoresponsive properties and undergo a coil-to-globule phase transition in water.…”

Section: Introductionmentioning

confidence: 99%

Precise Synthesis and Thermoresponsive Property of Poly(ethyl glycidyl ether) and Its Block and Statistic Copolymers with Poly(glycidol)

Wang

Narumi

et al. 2021

Polymers

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In this paper, we describe a comprehensive study of the thermoresponsive properties of statistic copolymers and multiblock copolymers synthesized by poly(glycidol)s (PG) and poly(ethyl glycidyl ether) (PEGE) with different copolymerization methods. These copolymers were first synthesized by ring-opening polymerization (ROP), which was initiated by tert-butylbenzyl alcohol (tBBA) and 1-tert-butyl-4,4,4-tris(dimethylamino)-2,2-bis[tris(dimethylamino)phosphoranylidenamino]-2Λ5,4Λ5-catenadi(phosphazene) (t-Bu-P4) as the catalyst, and then the inherent protective groups were removed to obtain the copolymers without any specific chain end groups. The thermoresponsive property of the statistic copolymer PGx-stat-PEGEy was compared with the diblock copolymer PGx-b-PEGEy, and the triblock copolymers were compared with the pentablock copolymers. Among them, PG-stat-PEGE, PG-b-PEGE-b-PG-b-PEGE-b-PG, and PEGE-b-PG-b-PEGE-b-PG-b-PEGE, and even the specific ratio of PEGE-b-PG-b-PEGE, exhibited LCST-type phase transitions in water, which were characterized by cloud point (Tcp). Although the ratio of x to y affected the value of the Tcp of PGx-stat-PEGEy, we found that the disorder of the copolymer has a decisive effect on the phase-transition behavior. The phase-transition behaviors of PG-b-PEGE, part of PEGE-b-PG-b-PEGE, and PG-b-PEGE-b-PG copolymers in water present a two-stage phase transition, that is, firstly LCST-type and then the upper critical solution temperature (UCST)-like phase transition. In addition, we have extended the research on the thermoresponsive properties of EGE homopolymers without specific α-chain ends.

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“…Building on this wide availability and background knowledge, PEO-based polymers have recently been explored as smart materials due to their low toxicity, biocompatibility, and thermoresponsive properties. , Solution properties such as the lower critical solution temperature (LCST), which describes the thermal stimuli-responsive behavior of solution state PEO, have been tailored for PEO-based materials by adding hydrophobic functionality to the PEO backbone. By use of this copolymer approach, a range of glycidyl ether monomers have been copolymerized with ethylene oxide (EO) through ring-opening polymerization to yield PEO derivatives exhibiting variations in cloud point temperature, which quantitatively determines LCST. − These glycidyl ether derivatives are typically based on thioether or triazole linkages, further differentiating the comonomer structure from the poly(ethylene oxide) backbone. A family of poly(glycidyl ether) homopolymers with methoxy and ethoxy-terminal oligo(ethylene oxide) 0–3 (OEO) side-chains have also been reported, and a proportional increase in cloud point with side-chain length has been demonstrated .…”

Section: Introductionmentioning

confidence: 99%

Role of Side-Chain Architecture in Poly(ethylene oxide)-Based Copolymers

et al. 2020

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Copolymerization of ethylene oxide and a series of glycidyl ethers with precise linear/cyclic oligo(ethylene oxide) side-chains allows access to a library of well-defined poly(ethylene oxide) (PEO)-based copolymers with 2–50 mol % side-chain functionality. The structure of the linear and cyclic oligo(ethylene oxide) glycidyl ether monomers influences the apparent reactivity ratios, which were consistent with gradient-type architectures. From these isomeric side-chain materials, the solution phase behavior, semicrystallinity, and ionic conductivity of the linear and crown ether side-chain functional copolymers were characterized and compared to conventional, linear PEO homopolymers. Incorporation of linear side-chains decreased the cloud point, whereas incorporation of the crown ether side-chain functionality did not affect the cloud point when compared to linear PEO. In contrast, an ion-selective response of the cloud point was observed for the crown ether side-chain copolymers with minimal response for the isomeric linear systems. In the solid state, the copolymer materials could be tuned from semicrystalline to completely amorphous as the incorporation of linear or cyclic comonomers was increased. Ionic conductivity was characterized by using both lithium and sodium bis(trifluoromethylsulfonyl)imide and found to be consistent with amorphous PEO-based copolymer materials. Linear side-chain functional copolymers exhibited significantly higher ionic conductivity than their crown ether side-chain analogues due to the lower T g of corresponding salt/copolymer blends. Finally, a readily available linear oligo(ethylene glycol) monomer based on a commercial starting material was prepared and copolymerized with ethylene oxide to give a copolymer with properties comparable to the corresponding precise analogues. These new structures allow for the development of property-tailored hydrophilic PEO-based copolymers for a variety of materials applications.

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(1‐Adamantyl)methyl Glycidyl Ether: A Versatile Building Block for Living Polymerization

Cited by 9 publications

References 77 publications

Polymerization of Ethylene Oxide, Propylene Oxide, and Other Alkylene Oxides: Synthesis, Novel Polymer Architectures, and Bioconjugation

Polymerization of Ethylene Oxide, Propylene Oxide, and Other Alkylene Oxides: Synthesis, Novel Polymer Architectures, and Bioconjugation

Precise Synthesis and Thermoresponsive Property of Poly(ethyl glycidyl ether) and Its Block and Statistic Copolymers with Poly(glycidol)

Role of Side-Chain Architecture in Poly(ethylene oxide)-Based Copolymers

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