Fluorinated allyl-, acetyl-, and bromo-containing hydroxyl-substituted phenyl ethers with a hexafluorobenzene or decafluorobiphenyl central unit

Ткаченко, І. М.; Shekera, О.V.; Bliznyuk, Valery N.; Shevchenko, V. V.

doi:10.1016/j.jfluchem.2013.02.009

Cited by 9 publications

(5 citation statements)

References 31 publications

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“…Partially fluorinated poly(arylene ether)s have been developed for application as fuel cell membranes, and their polymerisability and degradation during sulfonation were examined . A wide variety of bifunctional phenyl ethers having tetrafluorophenylene or octafluorobiphenylene moieties has been synthesized for optical or membrane applications . Tetrafluorophenylene-bridged bisphospholes were synthesized to analyze their photophysical and electrochemical properties .…”

Section: Introductionmentioning

confidence: 99%

“…1 A wide variety of bifunctional phenyl ethers having tetrafluorophenylene or octafluorobiphenylene moieties has been synthesized for optical or membrane applications. 2 Tetrafluorophenylene-bridged bisphospholes were synthesized to analyze their photophysical and electrochemical properties. 3 Similar perfluoroaromatic molecules have been explored for application to peptides and proteins; model cysteine compounds were prepared by nucleophilic aromatic substitution (S N Ar) with hexafluorobenzene and decafluorobiphenyl to study stapled peptides.…”

Section: ■ Introductionmentioning

confidence: 99%

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Reactions of Bifunctional Perfluoroarylsilanes with Activated C–F Bonds in Perfluorinated Arenes

Nishida

Fukaya

et al. 2019

ACS Omega

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Reactions of bifunctional perfluoroarylsilanes, p- and m-C6F4(SiMe3)2 as well as o-BrC6F4SiMe3, with substituted perfluoroarenes having electron-withdrawing groups were investigated using NMR and density functional theory calculation techniques. The C–F bond in perfluoroarenes was activated by the para-position of an electron-withdrawing group, such as CF3, C6F5, CN, and NO2. The reaction of C6F4(SiMe3)2 mainly occurred at the para-position of the perfluoroarenes and also occurred at the ortho-position of C6F5CN and C6F5NO2. Two equivalent reactions of perfluoroarenes with bifunctional p- and m-C6F4(SiMe3)2 provided disubstituted perfluoroarenes, along with a small amount of protonated monosubstituted perfluoroarenes. The reaction of o-BrC6F4SiMe3 with the CF3- and CN-substituted pentafluorobenzenes provided unexpected coupling products between C–Br and C–F bonds, in addition to the coupling products between C–SiMe3 and C–F bonds.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Reactions of Bifunctional Perfluoroarylsilanes with Activated C–F Bonds in Perfluorinated Arenes

Nishida

Fukaya

et al. 2019

ACS Omega

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“…Fluorinated isomeric hydroxyl‐containing monomers 4‐[2,3,5,6‐tetrafluoro‐4‐(4‐hydroxyphenoxy)phenoxy]phenol ( 3 ) and 3‐[2,3,5,6‐tetrafluoro‐4‐(3‐hydroxyphenoxy)phenoxy]phenol ( 4 ) were synthesized according to a previously reported protocol . Fluorinated allyl‐ and acetyl‐containing hydroxyl‐substituted phenyl ethers with a TFB central unit, 2‐(prop‐2‐en‐1‐yl)‐4‐{2,3,5,6‐tetrafluoro‐4‐[4‐hydroxy‐3‐(prop‐2‐en‐1‐yl)phenoxy]phenoxy}phenol ( 5 ) and 1‐{5‐[4‐(3‐acetyl‐4‐hydroxyphenoxy)‐2,3,5,6‐tetra‐fluorophenoxy]‐2‐hydroxyphenyl}ethan‐1‐one ( 6 ), respectively, were synthesized following previously reported routines . N ‐bromosuccinimide (NBS; 99%, Acros Organics) was used as received without further purification.…”

Section: Methodsmentioning

confidence: 99%

“…Previously we have reported the first successful synthesis of FPAEs having both TFB and octafluorobiphenylene units in their backbone based on the aforementioned dihydroxyl‐containing monomers and individual DFB . To further develop this approach, we have synthesized novel fluorinated aminomethyl‐, allyl‐, acetyl‐ and bromo‐containing hydroxyl‐substituted phenyl ethers with the TFB central unit . The presence of functional groups enables the appearance of new properties and offers interesting opportunities for further preparation of functionalized polymers (creation of multifunctional polymer systems).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of novel fluorinated poly(arylene ether)s

et al. 2015

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Dibromomethylene‐containing monomer with a tetrafluorobenzene central unit was synthesized using 2,3,5,6‐tetrafluoro‐1,4‐bis(4‐methylphenoxy)benzene as a starting material. This approach enabled preparation of several fluorinated poly(arylene ether)s containing isomeric fragments, with or without allyl or acetyl side groups, which were prepared by interaction of the synthesized tetrafluorobenzene‐based monomer with various types of hydroxyl‐substituted diphenyl ethers. The structure of the synthesized compounds was determined using Fourier transform infrared, 1H NMR and 19 F NMR spectroscopy techniques. Most of the resulting polyethers were soluble in chlorinated, ether‐type or polar amide solvents. The molecular weight, mechanical and thermal properties of the synthesized fluorinated poly(arylene ether)s were studied depending on the inherent isomery of macromolecular chains and the nature of functional groups. Some ways of functionalization of the prepared fluorinated polyethers with epoxy and triethoxysilyl groups were proposed. © 2015 Society of Chemical Industry

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“…phases. [24][25][26][27][28][29][30] It is interesting to note that such fluorinated liquid crystals have good stability, high voltage holding ratio, and specific resistance. Moreover, they are characterized with low threshold switching voltage (V th ) and small temperature coefficient of V th , and are, therefore, widely used now in LC displays.…”

Section: 4′-{(2356-tetrafluoro-14-phenylene)bis[oxy-41-phenylementioning

confidence: 99%

Synthesis and characterization of fluorinated poly(azomethine ether)s from new core-fluorinated azomethine-containing monomers

Kobzar

Ткаченко

Bliznyuk

et al. 2015

Designed Monomers and Polymers

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In this work, we describe the design and synthesis of novel core-fluorinated Schiff base monomers and conjugated polymers based on them. The new fully aromatic highly fluorinated poly(azomethine ether)s (PAMEs) were prepared by polycondensation of core-fluorinated azomethine-containing compounds. The structure of the monomers and polymers were confirmed by FTIR, F NMR spectroscopic analysis. The influence of synthesis condition on the properties of PAME compounds was investigated. Application of polarization microscopy with a temperature control thermal stage revealed thermotropic liquid crystalline (LC) behavior in the synthesized materials. Transition temperatures and a range of the existence of the LC phase were studied by a combination of the optical microscopy and DSC analysis. According to the TGA analysis, all the synthesized PAMEs show high thermal stability and thus offer a wide range of thermal processibility (up to 410-477 °C), which makes them prospective materials for many modern applications.

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Fluorinated allyl-, acetyl-, and bromo-containing hydroxyl-substituted phenyl ethers with a hexafluorobenzene or decafluorobiphenyl central unit

Cited by 9 publications

References 31 publications

Reactions of Bifunctional Perfluoroarylsilanes with Activated C–F Bonds in Perfluorinated Arenes

Reactions of Bifunctional Perfluoroarylsilanes with Activated C–F Bonds in Perfluorinated Arenes

Synthesis and properties of novel fluorinated poly(arylene ether)s

Synthesis and characterization of fluorinated poly(azomethine ether)s from new core-fluorinated azomethine-containing monomers

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