Synthetic access to an elusive high-temperature perfluoroisopropenyl ether prepolymer for radical copolymerization

Burgess, Trevor; Pasiuk, Addison D. G.; Jelier, Benson J.; Friesen, Chadron M.

doi:10.1039/c8cc05241g

Cited by 3 publications

(3 citation statements)

References 17 publications

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“…PIPE monomer was synthesized following the reaction reported in Scheme 1. 18 A second 50 mL three-necked round-bottomed flask with a magnetic stir bar was fitted as above, and then purged with nitrogen while cooling to room temperature. 1.00 molar equivalents of previously degassed oligo(hexafluoropropylene oxide) primary iodide (10.0 g, 6.16 mmol) was added by weighed syringe.…”

Section: Synthesis Of Oligo(hexafluoropropylene Oxide)-pipementioning

confidence: 99%

“…If there is any excess of phenyl lithium added, it will form a cascade of side products as reported in a former work. 18 Finally, the lithium perfluorocarbanion was slowly warmed from -78 o C to room temperature over an average of 3.5 h to generate the desired product (see Figures S1-S3). Phenyl adducts, which are impurities in the PIPE, can reach as high at 28% if the conditions are not achieved carefully.…”

Section: Synthesis Of Oligo(hexafluoropropylene Oxide)-pipementioning

confidence: 99%

“…In 2018, we communicated the formation of oligo(HFPO)-PIPE. 18 The best route to PIPE was using oligo(HFPO) primary iodide and treating the iodide with one equivalent of phenyl lithium at -78 o C in perfluorohexane/hexane mixture and then proceeding to slowly warm up the mixture to room temperature over 4 hours.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of poly[oligo(hexafluoropropylene oxide) perfluoroisopropenylether (PIPE)] graft copolymers with vinylidene fluoride (VDF) using CF₃radicals

et al. 2019

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Section: Synthesis Of Oligo(hexafluoropropylene Oxide)-pipementioning

confidence: 99%

Section: Synthesis Of Oligo(hexafluoropropylene Oxide)-pipementioning

confidence: 99%

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Synthesis of poly[oligo(hexafluoropropylene oxide) perfluoroisopropenylether (PIPE)] graft copolymers with vinylidene fluoride (VDF) using CF₃radicals

et al. 2019

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Super SEI‐Forming Anion for Enhanced Interfacial Stability in Solid‐State Lithium Metal Batteries

Song,

Tian,

Zhu

et al. 2024

Advanced Materials

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The extremely high chemical reactivity of lithium metal (Li°) electrodes and its enormous volume change during repetitive cycles cause continuous interfacial degradations in prevailing organic electrolytes, thus deteriorating the cycling performances of rechargeable lithium metal batteries (LMBs). Herein, departing from traditional wisdom on the design of electrolyte components, a super SEI‐forming anion (SSA), as an efficient percussor for building stable interphases on Li° electrode, is proposed. Comprehensive investigations related to the unique anion chemistry of SSA reveal that the sulfonate and polyfluoroalkyl functionalities synergistically contribute to uniform spatial distributions of designer interfacial species, greatly improving the surface coverage property and conformal ability of the resulting interphases. Consequently, the incorporation of SSA leads to significant improvements in the cyclability of Li° electrode (exceeding 575 mAh cm−2 before failure) and the corresponding rechargeable Li°||LiFePO4 cells [a five‐time increase in lifespan as compared to the benchmark cell with the popular SEI‐forming anion bis(fluorosulfonyl)imide (FSI)]. The present work offers a paradigm shift to tame the notorious interfacial issues via upgraded anion chemistry, which can promote the practical development of rechargeable LMBs and other kinds of metal batteries.

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Diversity of Synthetic Approaches to Functionalized Perfluoropolyalkylether Polymers

et al. 2021

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Perfluoropolyalkylethers (PFPAEs) are a class of fluorinated polymers having −OCF2–, −OCF2CF2–, and −OCF2CF(CF3)– as common chain units. The ether linkages distinguish them from other famous fluorinated polymers such as poly(tetrafluoroethylene). Their higher mobility highlighted by below zero glass transition temperatures permit them to be noncrystalline, which makes them easy to use for many applications. They possess interesting tribological properties, combined with an excellent thermal and chemical stability, make them very useful as lubricants. However, after chemical modifications, they also demonstrated to be very useful in numerous applications as surfactants, electrolytes, high performance coatings, vitrimers, or microfluidic devices, to give a few examples. This Perspective aims to summarize all the chemical modifications reported on these PFPAEs to provide a new insight into their potential utility in emerging fields. Indeed, the end group can modulate the properties of PFPAE-based materials such as lubricity, superhydrophobicity, biofouling, antibacterial activity, amphiphilicity, and the ability to react further with comonomers under photochemical and thermal processes. It can also modulate their intrinsic properties such as viscosity and solubility in common organic solvents. The chemical modifications are sorted in five main parts: the condensation reactions, the nucleophilic reactions, the click chemistry reactions, the radical reactions, and finally reactions going through other mechanisms or requiring a multistep process. They can be employed as such or for further polymerization processes depending on the targeted application. Examples of applications are thoroughly described to demonstrate their current usefulness and to help provide direction for their future use.

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Synthetic access to an elusive high-temperature perfluoroisopropenyl ether prepolymer for radical copolymerization

Cited by 3 publications

References 17 publications

Synthesis of poly[oligo(hexafluoropropylene oxide) perfluoroisopropenylether (PIPE)] graft copolymers with vinylidene fluoride (VDF) using CF₃radicals

Synthesis of poly[oligo(hexafluoropropylene oxide) perfluoroisopropenylether (PIPE)] graft copolymers with vinylidene fluoride (VDF) using CF₃radicals

Super SEI‐Forming Anion for Enhanced Interfacial Stability in Solid‐State Lithium Metal Batteries

Diversity of Synthetic Approaches to Functionalized Perfluoropolyalkylether Polymers

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Synthetic access to an elusive high-temperature perfluoroisopropenyl ether prepolymer for radical copolymerization

Cited by 3 publications

References 17 publications

Synthesis of poly[oligo(hexafluoropropylene oxide) perfluoroisopropenylether (PIPE)] graft copolymers with vinylidene fluoride (VDF) using CF3radicals

Synthesis of poly[oligo(hexafluoropropylene oxide) perfluoroisopropenylether (PIPE)] graft copolymers with vinylidene fluoride (VDF) using CF3radicals

Super SEI‐Forming Anion for Enhanced Interfacial Stability in Solid‐State Lithium Metal Batteries

Diversity of Synthetic Approaches to Functionalized Perfluoropolyalkylether Polymers

Contact Info

Product

Resources

About

Synthesis of poly[oligo(hexafluoropropylene oxide) perfluoroisopropenylether (PIPE)] graft copolymers with vinylidene fluoride (VDF) using CF₃radicals

Synthesis of poly[oligo(hexafluoropropylene oxide) perfluoroisopropenylether (PIPE)] graft copolymers with vinylidene fluoride (VDF) using CF₃radicals