Anionic ring-opening polymerization of ethylene oxide in DMF with cyclodextrin derivatives as new initiators

Huin, Cécile; Eskandani, Zahra; Badi, Nezha; Farcas, Aurica; Bennevault‐Celton, Véronique; Guégan, Philippe

doi:10.1016/j.carbpol.2012.12.062

Cited by 24 publications

(18 citation statements)

References 33 publications

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“…When using a multifunctional initiator in anionic polymerization, the dissociation equilibrium between free ions and aggregates tended to move toward the aggregates during the exchange reactions between the dormant species (alcohols) and the active species (alkoxides) . Huin et al . reported that during the polymerization of ethylene oxide initiated by cyclodextrins, a small amount of diphenylmethylpotassium (DPMK) as catalyst is necessary and allows a control of the polymerization reactions.…”

Section: Resultsmentioning

confidence: 99%

“…They were first obtained by living anionic polymerization in the 1950s and have been the subject of extensive research since then because of their topological structures and their unique chemical and physical properties, that is, encapsulation abilities due to their 3D globular structures . Star polymers are often synthesized by one of the following four strategies: “arm‐first,” “core‐first,” “coupling‐onto,” and “iterative methodology” by radical, metal alkylidene, anionic, and cationic polymerization processes. Each of these approaches has certain advantages and disadvantages that must be taken into consideration according to the desired macromolecular architecture and involved chemistry.…”

Section: Introductionmentioning

confidence: 99%

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β‐Cyclodextrin‐Based Star Amphiphilic Copolymers: Synthesis, Characterization, and Evaluation as Artificial Channels

Faye

Huin

Illy

et al. 2018

Macro Chemistry & Physics

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14‐arm amphiphilic star copolymers are synthesized according to different strategies. First, the anionic ring polymerization of 1,2‐butylene oxide (BO) initiated by per(2‐O‐methyl‐3,6‐di‐O‐(3‐hydroxypropyl))‐β‐CD (β‐CD’OH14) and catalyzed by t‐BuP4 in DMF is investigated. Analyses by NMR and SEC show the well‐defined structure of the star β‐CD’‐PBO14. To obtain a 14‐arm poly(butylene oxide‐b‐ethylene oxide) star, a Huisgen cycloaddition between an α‐methoxy‐ω‐azidopoly(ethylene oxide) and the β‐CD’‐PBO14,whose end‐chains are beforehand alkyne‐functionalized, is performed. In parallel, 14‐arm star copolymers composed of butylene oxide‐b‐glycidol arms are successfully synthesized by the anionic polymerization of ethoxyethylglycidyl ether (EEGE) initiated by β‐CD’‐PBO14 with t‐BuP4. The deprotection of EEGE units is then performed to provide the polyglycidol blocks. These amphiphilic star polymers are evaluated as artificial channels in lipid bilayers. The effect of changing a PEO block by a polyglycidol block on the insertion properties of these artificial channels is discussed.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

β‐Cyclodextrin‐Based Star Amphiphilic Copolymers: Synthesis, Characterization, and Evaluation as Artificial Channels

Faye

Huin

Illy

et al. 2018

Macro Chemistry & Physics

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“…The presence of water in the reaction mixture may be debated, however, it was previously stated that, even with thorough procedures of water removal from cyclodextrin, water traces are still present [7]. Moreover, it was shown recently [18] that water is actually improving the overall process in case of bulk polymerization of ε-caprolactone (CL) under conditions of increased pressure.…”

Section: Resultsmentioning

confidence: 99%

“…are already available as commercial products, the modification with polymers is still under development [4–5]. So far, several polymerization reactions were used for CD modification, including free radical polymerization, reversible-deactivation radical polymerizations [5] as well as ring opening polymerizations (ROP) of cyclic esters [6], oxiranes [7] and oxazolines [8]. However, the ROP of cyclic esters should also be considered as a method of producing polymer-modified CDs with some particular features, such as possibility of employing green polymerization procedures and availability of renewable monomers like cyclic esters.…”

Section: Introductionmentioning

confidence: 99%

Cyclodextrins tethered with oligolactides – green synthesis and structural assessment

Peptu¹,

Balan-Porcăraşu²,

Šišková³

et al. 2017

Beilstein J. Org. Chem.

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Biodegradable oligolactide derivatives based on α-, β- and γ-cyclodextrins (CDs) were synthesized by a green procedure in which CDs play the role of both the initiator and the catalyst. The synthetic procedure in which CDs and L-lactide (L-LA) are reacting in bulk at relatively high temperature of 110 °C was investigated considering the structural composition of the products. The obtained products were thoroughly characterized via mass spectrometry methods with soft ionization like matrix-assisted laser desorption ionization (MALDI) and electrospray ionization (ESI). Liquid chromatography (LC) separation with evaporative light scattering detection (ELSD) and NMR analysis were employed in order to elucidate the structural profiles of the obtained mixtures. The results clearly demonstrate that the cyclodextrins were tethered with more than one short oligolactate chain per CD molecule, predominantly at the methylene group, through ring opening of L-LA initiated by primary OH groups.

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“…Thus, these host molecules found vast applications as artificial enzymes, drug carriers, nanopores, catalyst, and chemosensors, to name but a few . Most of CD‐based polymers are star polymers with a CD core or linear polymer with dangling CD grafted on a macromolecular backbone . However, these strategies involved monomers from fossil resources.…”

Section: Introductionmentioning

confidence: 99%

Chemical Sensors Based on New Polyamides Biobased on (Z) Octadec‐9‐Enedioic Acid and β‐Cyclodextrin

Duarte

Nag

Castro

et al. 2016

Macro Chemistry & Physics

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International audienceThe synthesis of new biobased polyamides from different β-cyclodextrin monomers and the (Z) octadec-9-enedioic acid is investigated. The aim of this study is to design different sensors, having different sensibilities and selectivities to a set of various volatile organic compounds (VOC) relevant in the early detection of lung cancer. The sensors are obtained from the synthesized polyamides, using multiwalled carbon nanotubes as conductive nanofillers and a layer by layer process. The conductive polymer nanocomposites (CPC) designed from the heptakis-6-amino β-cyclodextrin and 6A,6D diamino β-cyclodextrin have a high affinity for polar protic solvents, while the CPC having a matrix based on 6A,6D diamino 2A-G,3A-G,6B,6C,6E,6F,6G nonadeca-O-benzyl-β-cyclodextrin develops hydrophobic interactions with nonpolar solvents. Due to a higher accessibility of cyclodextrin, the chemoresistive response of the hydrophilic linear polyamide CPC is larger than one of the hydrophilic branched polyamide CPC. As required, the VOC diffusion/desorption phenomenon is reversible for all the sensors

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Anionic ring-opening polymerization of ethylene oxide in DMF with cyclodextrin derivatives as new initiators

Cited by 24 publications

References 33 publications

β‐Cyclodextrin‐Based Star Amphiphilic Copolymers: Synthesis, Characterization, and Evaluation as Artificial Channels

β‐Cyclodextrin‐Based Star Amphiphilic Copolymers: Synthesis, Characterization, and Evaluation as Artificial Channels

Cyclodextrins tethered with oligolactides – green synthesis and structural assessment

Chemical Sensors Based on New Polyamides Biobased on (Z) Octadec‐9‐Enedioic Acid and β‐Cyclodextrin

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