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

Abstract

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

Development of a light-responsive fluorinated poly(arylene ether) copolymer containing azobenzene groups in the main polymer chain

“…This choice is based on our previous results, which demonstrate that meta -connecting polymers possess enhanced solubility, thermostability and mechanical properties. 38…”

“…This choice is based on our previous results, which demonstrate that meta-connecting polymers possess enhanced solubility, thermostability and mechanical properties. 38 The success of the synthesis of the Azo-coFPAE is confirmed with 1 H NMR, 19 F NMR, FTIR and Raman spectroscopy techniques. All peaks in the 1 H NMR spectrum of the representative copolyether Azo-coFPAE can be readily assigned to the protons in the corresponding repeat units (Fig.…”

Per-Fluorinated Azo- and Azomethane-Based Organic Polymers Developed Via Nucleophilic Aromatic Substitution Mechanism: Synthesis, Thermal, Optical Properties, Porosity and Environmental Applications

“…Further steps of the reaction mechanism are enclosed in Scheme S1. This polymerization methodology has been applied to prepare several reported per uorinated organic polymers [1,4,10,21]. According to literature, the polymers that contain HFB or DFB linkers were prepared under mild conditions of relatively low temperatures that did not exceed 80 °C with long stirring time [22].…”

“…Regarding the NAS, the synthetic methodology relies on successfully substituting the C-F bond with strong nucleophiles containing oxygen such as aromatic phenoxide or aliphatic alkoxides. Examples of this type include: small-molecule or polymer chains such as uorinated poly(aryl ether), poly(aliphatic ethers), poly(ether ketone)s, poly(ether sulfone)s, and poly(ether nitrile)s [11,[17][18][19][20][21]. This principle is also applied to diamines and dithiols for the preparation of uorinated polyamines or uorinated poly(sul de).…”

Synthesis, Characterization, and Environmental Applications of Novel Per-Fluorinated Organic Polymers with Azo- and Azomethine-Based Linkers via Nucleophilic Aromatic Substitution

“…In the NAS synthetic methodology, successful substitution of the C-F bond is achieved by using strong nucleophiles containing oxygen, such as aromatic phenoxide or aliphatic alkoxides. This methodology is employed with various small molecules or polymer chains such as fluorinated poly(aryl ether), poly(aliphatic ethers), poly(ether ketone)s, poly(ether sulfone)s, and poly(ether nitrile)s [11,[18][19][20][21][22]. The above-mentioned principle is also employed in the preparation of fluorinated polyamines or fluorinated poly(sulfide) using diamines and dithiols [23,24].…”