Novel fluoropolymers formed by an unprecedented SRN1 condensation polymerization mechanism

Rodriguez‐Garcia, Valerie; Wu, Kai; Angerhofer, Alexander; Hedhli, Lotfi; Elsheikh, Maher

doi:10.1016/j.jfluchem.2008.02.010

Cited by 7 publications

(6 citation statements)

References 12 publications

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“…Scheme 36. Synthesis of the copolymer via condensation mechanism, [177] where CVD stands for chemical vapor deposition. Reproduced with permission from Elsevier.…”

Section: Cobalt-mediated Radical Copolymerization Of Chlorotrifluoroethylene and Vinyl Acetatementioning

confidence: 99%

Macromolecular engineering approach for the preparation of new architectures from fluorinated olefins and their applications

Mohammad

Shingdilwar

Banerjee

et al. 2020

Progress in Polymer Science

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An overview on fluorinated olefins-based architectures prepared by reversible deactivation radical polymerization (RDRP) techniques and applications is presented. Controlled synthesis of well-defined fluoropolymers is discussed as a route to prepare tailored macromolecules of various architectures, such as homopolymers, block copolymers (BCPs), graft copolymers, and star/miktoarms[1]. Primary examples of different strategies of synthesis include (a) Iodine Transfer Polymerization (ITP), (b) Reversible Addition-Fragmentation Chain Transfer /Macromolecular Design via the Interchange of Xanthates (RAFT/MADIX) polymerization, (c) Atom Transfer Radical Polymerization (ATRP), (d) Nitroxide Mediated Polymerization (NMP), (e) Organometallic-Mediated Radical Polymerization (OMRP) and (f) Others systems (based on borinates, Tellurium, and other complexes). Synthesis of BCPs and graft copolymers using these polymerization techniques of vinylidene Fluoride (VDF), chlorotrifluoroethylene (CTFE) and other fluorinated monomers was also discussed, as well as using Copper(I)-catalyzed azide-alkyne cycloaddition (click chemistry). Phase behavior and self-assembly of the fluorinated block copolymers were also discussed. Special attention was devoted to the applications of fluoropolymer architectures in producing thermoplastic elastomers, medical tactile sensors, fuel cells membranes, functional coatings, electroactive polymers (e.g. piezoelectric/ferroelectric/dielectric devices and actuators), high energy storage capacitors, surfactants and composites.

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“…Scheme 36. Synthesis of the copolymer via condensation mechanism, [177] where CVD stands for chemical vapor deposition. Reproduced with permission from Elsevier.…”

Section: Cobalt-mediated Radical Copolymerization Of Chlorotrifluoroethylene and Vinyl Acetatementioning

confidence: 99%

Macromolecular engineering approach for the preparation of new architectures from fluorinated olefins and their applications

Mohammad

Shingdilwar

Banerjee

et al. 2020

Progress in Polymer Science

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“…Parylene AF-4 is a high-temperature stable polymer for conformal coatings with a broad field of applications [1][2][3]. It is produced by chemical vapour deposition (CVD) via the Gorham method [4].…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, using DMPU on reflux gave a modest yield of 78%. Earlier protocols like the one of Dolbier et al [3] used highly toxic HMPA. We decided to replace it by DMPU, which poses a far smaller safety hazard and environmental concerns, and is therefore a very important consideration for scale-up [15].…”

Section: Introductionmentioning

confidence: 99%

“…The solvent HMPA is known to favour S N 2 reactions and to increase their rate. How exactly the mechanism works is though not clear among all authors of previous related publications [3,16,17]. In microwave reactions and subsequent qNMR studies, the influence of temperature, time and excess molar equivalents of sodium phenolate were compared.…”

Section: Introductionmentioning

confidence: 99%

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Improved route to a diphenoxide-based precursor for chemical vapour deposition of parylene AF-4

2021

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In this work, we present the synthesis of an alternative precursor for chemical vapour deposition of parylene AF-4 to the widely used standard, octafluoro[2.2]paracyclophane. The standard precursor suffers from uncertainties in its supply chain and its synthesis is of low yield. A comparison between different reaction parameters and solvents is drawn by means of thermal, laboratory-scale and microwave-assisted reactions and quantitative nuclear magnetic resonance (qNMR) studies.

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“…Among fluorinated functional groups, the bromodifluoromethyl (CF 2 Br) group is a versatile one because various bromodifluoromethylated aromatics have served as precursors of [ 18 F]trifluoromethylated compounds for positron emission tomography (PET) imaging, 2 liquid crystal (LC) compounds containing a -CF 2 OAr moiety, 3 fluoroparacyclophanes, 4 and fluorinated polymers (Scheme 1). 5 In addition, the CF 2 Br group can be regarded as an equivalent of trifluoromethyl (CF 3 ) 2 and difluoromethyl (CHF 2 ) 6 groups. To introduce the CF 2 Br group via carbonAcarbon bond formation, dibromodifluoromethane (CF 2 Br 2 ) has been used as a source of the CF 2 Br group and several bromodifluoromethylations of carbon nucleophiles, such as acetylides 7 and enolates, 6c,8 were reported.…”

Section: Introductionmentioning

confidence: 99%

Bromodifluoromethylation of aromatic Grignard reagents with CF2Br2

Shiosaki

Inoue

2014

Tetrahedron Letters

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Novel fluoropolymers formed by an unprecedented SRN1 condensation polymerization mechanism

Cited by 7 publications

References 12 publications

Macromolecular engineering approach for the preparation of new architectures from fluorinated olefins and their applications

Macromolecular engineering approach for the preparation of new architectures from fluorinated olefins and their applications

Improved route to a diphenoxide-based precursor for chemical vapour deposition of parylene AF-4

Bromodifluoromethylation of aromatic Grignard reagents with CF2Br2

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