Synthesis and lithium transport in ionically conducting crown ether polymers

Collie, L.; Parker, David; Tachon, C.; Hubbard, H. V. Saint A.; Davies, G. R.; Ward, I. M.; Wellings, Simon C.

doi:10.1016/0032-3861(93)90877-d

Cited by 17 publications

(11 citation statements)

References 9 publications

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“…Crown ethers are an important class of compounds that undergo complexation with metal ions and other species, in some cases leading to the formation of threaded structures known as pseudorotaxanes and rotaxanes . Polymers containing small crown ethers, most commonly 18-membered rings, were known as early as 1970, mainly for study of cation binding. − Polyaramides derived from dibenzo-18-crown-6 have been made via interfacial polymerization of diaminodibenzo-18-crown-6 with aromatic and aliphatic diacid chlorides. − A variety of other approaches has produced polymers containing crown ethers. − …”

Section: Introductionmentioning

confidence: 99%

“…[5][6][7] A variety of other approaches has produced polymers containing crown ethers. [8][9][10][11][12][13][14] In our laboratory, we have utilized crown ethers to synthesize a variety of polypseudorotaxanes and polyrotaxanes (Scheme 1). 2,[15][16][17][18][19][20][21][22][23][24][25][26] By carrying out step-growth polymerizations in the presence of crown ethers, main chain polypseudorotaxanes of type A (Scheme 1) were prepared based on polyester 15,16 and polyurethane backbones.…”

Section: Introductionmentioning

confidence: 99%

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Polyamide Pseudorotaxanes, Rotaxanes, and Catenanes Based on Bis(5-carboxy-1,3-phenylene)-(3x+2)-crown-x Ethers

et al. 2004

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We previously reported that the polyamide 3a derived from bis(5-carboxy-1,3-phenylene)-32-crown-10 (BCP32C10, 1a) and 4,4‘-oxydianiline (ODA, 2) was completely insoluble and attributed this to the formation of mechanical cross-links via self-threading of the crown ether moieties by the amide backbone through hydrogen bonding. Moreover, polycondensation of 1a with bis[4-(m-aminophenoxy)phenyl]phenylphosphine oxide (m-BAPPO, 4) produced polyaramide 5a that, like its analogue 3a, was insoluble in all solvents examined, including H2SO4. In the present work bis(5-carboxy-1,3-phenylene)−(3x+2)-crown-x ethers [BCP(3x+2)Cx] with 26-membered (BCP32C10, 1b), 20-membered (BCP20C6, 1c) and 14-membered (BCP14C4, 1d) rings were utilized to investigate further the proposed topological branching via in situ threading during polymerization. Condensation of BCP26C8 (1b) with ODA (2) and m-BAPPO (4) gave two new poly(amide crown ether)s, 3b and 5b, which were soluble in dipolar aprotic solvents. However, the GPC traces of aramides 3b and 5b exhibited bimodal behavior indicative of two distinct molecular weight fractions, one very high, DPn > 800! Similarly the aramide 3c formed by condensation of BCP20C6 (1c) and ODA (2) displayed a bimodal GPC curve. As a reference system BCP14C4 (1d) was prepared and polymerized with ODA; the resultant aramide 3d displayed a monomodal GPC trace and relatively narrow molecular weight distribution. Mass spectrometric studies show that cyclic aramides (lactams) form in the larger crown ether-based systems 3b and 5b. Model aramide 6 from isophthalic acid and ODA also contains cyclic polymers, as expected from Kricheldorf's recent results, but has a “normal” molecular weight distribution. Mass spectrometric examination of aramides 3c and 3d does not indicate any cyclic polymer formation. Inasmuch as lactam formation by itself does not necessarily produce branching or cross-linking, e.g., 6, we conclude that threading of the crown ether moieties is the key step, leading to polypseudorotaxane, polyrotaxane and polycatenane structures to an extent dependent upon the their cavity size and the propensity for cyclization of the polymer backbone.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Polyamide Pseudorotaxanes, Rotaxanes, and Catenanes Based on Bis(5-carboxy-1,3-phenylene)-(3x+2)-crown-x Ethers

et al. 2004

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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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“…A typical example of such materials are poly(crown ether)s, obtained by the polymerization of crown ether bearing olefin or acrylate monomers. [ 112 ] Hawker et al. synthesized copolymers of ethylene oxide and glycidyl ethers with cyclic oligo (ethylene oxide) side chains ( Figure a), which showed an ion matching effect, leading to different cloud point responses.…”

Section: Well‐defined Polymer Matricesmentioning

confidence: 99%

Structure Code for Advanced Polymer Electrolyte in Lithium‐Ion Batteries

Wang

Zhen

et al. 2020

Adv Funct Materials

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Over the past decade, lithium‐ion batteries (LIBs) have been widely applied in consumer electronics and electric vehicles. Polymer electrolytes (PEs) play an essential role in LIBs and have attracted great interest for the development of next‐generation rechargeable batteries with high energy density. Due to the several practical applications of LIBs and high demands for LIBs performance, many state‐of‐the‐art PEs with different structures and functionalities have been developed to regulate the LIBs performance, especially their rate capability, cycling durability, and lifespan. In this review, the recent advances in high‐performance LIBs prepared using well‐defined PEs are summarized. The ion‐transport mechanisms and preparation techniques of various well‐defined PE classes compared to conventional PEs are also discussed. The aim is to elucidate the structure code for advanced PEs with optimized properties, including ionic conductivity, mechanical properties, processability, accessibility, etc. The existing challenges and future perspectives are also discussed, setting the basis for designing novel PEs for energy conversion applications.

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Synthesis and lithium transport in ionically conducting crown ether polymers

Cited by 17 publications

References 9 publications

Polyamide Pseudorotaxanes, Rotaxanes, and Catenanes Based on Bis(5-carboxy-1,3-phenylene)-(3x+2)-crown-x Ethers

Polyamide Pseudorotaxanes, Rotaxanes, and Catenanes Based on Bis(5-carboxy-1,3-phenylene)-(3x+2)-crown-x Ethers

Cation Complexation and Conductivity in Crown Ether Bearing Polyphosphazenes

Structure Code for Advanced Polymer Electrolyte in Lithium‐Ion Batteries

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