Synthesis of functionalised 12-,13- and 14-membered crown ethers bearing exocyclic polymerisable groups and the binding properties and conductivities of their lithium doped polymers

Collie, L.; Denness, James E.; Parker, David; O'Carroll, Fiona; Tachon, C.

doi:10.1039/p29930001747

Cited by 15 publications

(9 citation statements)

References 5 publications

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“…A methacrylate derivative containing crown ether (CMA), 1 , was prepared according to a previous report . Analogous compounds CMA ( 2 − 4 ) were prepared by the modified Parkers' procedure illustrated in Scheme 2 …”

Section: Resultsmentioning

confidence: 99%

“…2-Hydroxymethyl-15-crown-5 (Tokyo Kasei Kogyo Co., Inc., Extra Pure), thallium ethoxide (Aldrich, 98%), methacryloyl chloride (Tokyo Kasei Kogyo Co., Inc., >80.0%), and 15-crown-5-ether (Tokyo Kasei Kogyo Co., Inc., >97%) were used as received. Methacryloyloxymethyl-15-crown-5 (1), 6 2-(2-bromoethyloxy)tetrahydropyran (5), 7 2-(6-bromohexyloxy)tetrahydropyran (6), 8 and 2-(12-bromododeceyloxy)tetrahydropyran (7) 9 were prepared according to reported procedures.…”

Section: Methodsmentioning

confidence: 99%

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Efficient Fixation of Carbon Dioxide into Poly(glycidyl methacrylate) Containing Pendant Crown Ether

2003

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The copolymers (CP1 − CP4) of glycidyl methacrylate (GMA) and methacrylate derivatives bearing 15-crown-5-ether (1 − 4) with M n of 9100−12 300 were prepared under radical conditions, and they were employed for the fixation of CO2 using NaI as a catalyst in nitromethane. The conversion of oxirane groups to carbonate by fixation of CO2 increased remarkably compared to the homopolymer of GMA. In the case of CP1, the reaction proceeded readily even in a dilute reaction system. Poly-GMA could convert into the corresponding polymer containing a carbonate moiety by the introduction of crown ether into the polymer backbone.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Efficient Fixation of Carbon Dioxide into Poly(glycidyl methacrylate) Containing Pendant Crown Ether

2003

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“…Through this strategy, well‐defined polymers with crown ether encircled in their main chains could be prepared with convenience. This is of great importance to the researches of crown ether containing polymers which are very useful functional materials or sensors . For instance, in early days, Kakuchi and coworkers had developed a series of cyclopolymerization strategies of difunctional monomers bearing an OEG chain to produce polymers with crown cavities for investigating the relevant metal ions binding properties .…”

Section: Introductionmentioning

confidence: 99%

Cyclopolymerization of α,ω‐heterodifunctional monomers containing styrene and maleimide moieties

Zou

Liu

Zhang

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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A series of α,ω‐heterodifunctional monomers with styrene (St) and maleimide moieties bridged by a varied length of oligo‐ethylene glycol (OEG) linkers were synthesized. Cyclopolymerizations of these monomers through reversible addition–fragmentation chain transfer‐mediated alternating radical copolymerization between intramolecular St and maleimide moieties were investigated. For the monomers with three or more ethylene glycol (EG) units, their cyclopolymerizations can be realized properly in low monomer feeding concentrations, affording well‐defined cyclopolymers with crown ether encircled in their main chains. Importantly, the cyclopolymerizations of monomers with six or seven EG units in the presence of KPF6 could be enhanced by the supramolecular effects between the OEG linkers and the potassium metal ion. Thus, the monomer feeding concentration could be largely improved, which may benefit preparation of the cyclopolymers with high degrees of copolymerization. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 330–338

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“…Parker and co-workers reported the synthesis of polyacrylates and polymethacrylates bearing 12- and 14-crown-4 ethers and the measurement of the ionic conductivity of these polymers when complexed with lithium perchlorate and triflate salts. − Of these two macrocylces, 14-crown-4 forms the more stable 1:1 complex with lithium. The polymers bearing 12-crown-4 units showed the higher ionic conductivities.…”

Section: Introductionmentioning

confidence: 99%

Cation Complexation and Conductivity in Crown Ether Bearing Polyphosphazenes

1998

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An attempt has been made to understand the mechanism of ionic conductivity in polyphosphazene−salt complexes by the synthesis and study of systems with crown ether side groups and salts with different cations. Amorphous phosphazene polymers, bearing either (12-crown-4)-methoxy, (15-crown-5)-methoxy, or (18-crown-6)-methoxy pendent groups, either as single-substituent polymers or mixed-substituent species in a 1:3 ratio with 2-(2-methoxyethoxy)ethoxy groups, were synthesized and characterized. The polymers in which all the side groups are crown ether units have glass transition temperatures higher than other oligo(ethyleneoxy) polyphosphazenes. They generate relatively low ionic conductivities at ambient temperatures when complexed with lithium triflate or lithium perchlorate. This suggests that the cation carries a significant part of the current in ether-type polymers. The ambient temperature ionic conductivity of the cosubstituent polyphosphazenes, as well as of poly[bis(2-(2-methoxyethoxy)ethoxy)phosphazene] (MEEP) (3), when complexed with MClO4 (M = Li, Na, K, Rb, Cs), was measured. The ionic conductivity is reduced when a favorable 1:1 or 2:1 crown ether−cation complex is formed. The thermal behavior of these polymer−salt complexes was also investigated. The polymers exhibit an increased glass transition temperature when a favorable 2:1 crown ether−cation complex is formed. The relationships between the ionic conductivity and the glass transition temperature of the host polymer electrolytes and the stability of the crown ether−cation complexes formed are discussed.

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Synthesis of functionalised 12-,13- and 14-membered crown ethers bearing exocyclic polymerisable groups and the binding properties and conductivities of their lithium doped polymers

Cited by 15 publications

References 5 publications

Efficient Fixation of Carbon Dioxide into Poly(glycidyl methacrylate) Containing Pendant Crown Ether

Efficient Fixation of Carbon Dioxide into Poly(glycidyl methacrylate) Containing Pendant Crown Ether

Cyclopolymerization of α,ω‐heterodifunctional monomers containing styrene and maleimide moieties

Cation Complexation and Conductivity in Crown Ether Bearing Polyphosphazenes

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