Synthesis and properties of novel soluble fluorinated aromatic polyamides containing 4-benzoyl-2,3,5,6-tetrafluorophenoxy pendant groups

Tang, Huali; Huang, Bin; Xie, Xiujun; Yan, Tao; Cai, Mingzhong

doi:10.1007/s10965-018-1454-1

Cited by 11 publications

(3 citation statements)

References 39 publications

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“…Other functional groups, e.g., PhthN– ( 1m ), −NH 2 ( 1n ), −COOH ( 1o ), and MeO 2 C– ( 1p ), were also compatible with the present conditions. Delightfully, 2,3,4,5,6-pentafluoro-substituted 1,2-diarylalkene ( 1r ) also worked well to produce 2,3,4,5,6-pentafluorobenzophenone with a decent yield, which is frequently used in the synthesis of OLED and F-containing polymers . More importantly, heterocycle-substituted internal alkenes, such as 2-styrylthiophene ( 1t ) and 2-styrylpyridine ( 1s ), are compatible with this catalytic system, delivering their respective ketones in 71% and 77% yield, respectively.…”

Section: Resultsmentioning

confidence: 94%

A Bifunctional Iron Nanocomposite Catalyst for Efficient Oxidation of Alkenes to Ketones and 1,2-Diketones

Song

Ren

et al. 2020

ACS Catal.

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We herein report the fabrication of a bifunctional iron nanocomposite catalyst, in which two catalytically active sites of Fe−N x and Fe phosphate, as oxidation and Lewis acid sites, were simultaneously integrated into a hierarchical N,P-dual doped porous carbon. As a bifunctional catalyst, it exhibited high efficiency for direct oxidative cleavage of alkenes into ketones or their oxidation into 1,2-diketones with a broad substrate scope and high functional group tolerance using TBHP as the oxidant in water under mild reaction conditions. Furthermore, it could be easily recovered for successive recycling without appreciable loss of activity. Mechanistic studies disclose that the direct oxidation of alkenes proceeds via the formation of an epoxide as intermediate followed by either acid-catalyzed Meinwald rearrangement to give ketones with one carbon shorter or nucleophilic ring-opening to generate 1,2-diketones in a cascade manner. This study not only opens up a fancy pathway in the rational design of Fe−N−C catalysts but also offers a simple and efficient method for accessing industrially important ketones and 1,2-diketones from alkenes in a cost-effective and environmentally benign fashion.

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Section: Resultsmentioning

confidence: 94%

A Bifunctional Iron Nanocomposite Catalyst for Efficient Oxidation of Alkenes to Ketones and 1,2-Diketones

Song

Ren

et al. 2020

ACS Catal.

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“…Polyarylamides and poly(amide-imide)s are widely known as high-performance polymeric materials characterized by light weight, thermal and chemical resistance, and superior mechanical properties. , However, the interchain interactions (mainly hydrogen bonding) in the polymers are strong which worsens their solubility and processability. In order to solve this problem, scientists have been long seeking alternative strategies to improve their solubility by introducing flexible linkages, , bulky side groups, , alkyl structures, etc. However, such modification on polymer backbones leads to a decrease in both T g s and thermal stability.…”

Section: Introductionmentioning

confidence: 99%

Significant Influence of Alkyl Substituents in the Alicyclic Rigid Backbone on Solubility and Thermal Stability of Polyarylamide Copolymers

Jin

Sun

Feng

et al. 2021

ACS Appl. Polym. Mater.

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Incorporation of alicyclic structural units in a polymer backbone holds great promises for preparing polyarylamides with superior physical properties (solubility, optical transparency, thermal stability, etc.). In this study, the alicyclic-containing building block, tetraethyl-substituted dibenzocyclooctadiene (TE-DBCOD), was integrated into the backbone of polyarylamides through a unique diamine monomer, TE-DBCOD-NH 2 . The TE-DBCOD-containing polyarylamides were synthesized first through polycondensation with different contents of TE-DBCOD units. Compared to the control polymers without DBCOD or ethyl side-chain units, the polyarylamides with TE-DBCOD units showed better solubility in less polar solvents (m-cresol, pyridine, and tetrahydrofuran) and higher glass transition temperature (T g ), which provides an opportunity to fabricate polyarylamides with both improved solubility and T g . Meanwhile, we also prepared the poly(amide-imide)s with TE-DBCOD by a two-step method for comparison. In contrast, the aromatic poly(amide-imide)s showed better solubility and lower T g s than the corresponding aromatic poly(amide-imide)s without TE-DBCOD contents, which revealed the complex influence of structure parameters on different polymers. Additionally, the synthesized polymers possessed high thermal stability (5% weight loss temperature > 440 °C) verified by thermogravimetric analysis. The strategy of introducing short side chains in polymer backbones opens a window for exploration of polymers with improved solubility and increased T g simultaneously, which also facilitates the understanding of the structure−property relationship of polymers with alicyclic structural units.

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“…Cai et al [116] prepared a novel diaroyl chloride monomer, via nucleophilic substitution reaction. The polymeric series containing fluorophenoxy unit was synthesized by taking different aromatic diamines as shown in (Scheme 31, P31).…”

Section: Aromatic Pas Covering Fluorescence Propertymentioning

confidence: 99%

Progress in the chemistry of functional aramids properties

Mishra

Madhad

Vasava

2021

Journal of Heterocyclic Chem

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High-performance polymers based on amide aromatic rings are known as wholly aromatic polyamides or aramids. The arrangement and admirable properties of aramids are built on the basis of amide linkage and rigid aromaticity. Aramids are attractive because of their extraordinary bond strengths and very high stiffness. Synthetic aromatic polymeric chains provide increased mechanical resistance and thermal softening compared to aliphatic aramids.In addition, aramids exhibit high thermal stability, low creep, and good optical activity with fluorescence. Hence, aramids are found in advanced arenas for engineering thermoplastics such as transport applications, electroactive materials, films, bullet-proof body armor, smart materials, protective clothing, fibers, in nanocomposites as asbestos alternatives, cutting edge complexes in arming, high-temperature lining material, in space engineering, and more. The objective of this review is to make the field of aramids functionality more accessible to the materials science community, that is, scientists, academicians, and engineers.

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Synthesis and properties of novel soluble fluorinated aromatic polyamides containing 4-benzoyl-2,3,5,6-tetrafluorophenoxy pendant groups

Cited by 11 publications

References 39 publications

A Bifunctional Iron Nanocomposite Catalyst for Efficient Oxidation of Alkenes to Ketones and 1,2-Diketones

A Bifunctional Iron Nanocomposite Catalyst for Efficient Oxidation of Alkenes to Ketones and 1,2-Diketones

Significant Influence of Alkyl Substituents in the Alicyclic Rigid Backbone on Solubility and Thermal Stability of Polyarylamide Copolymers

Progress in the chemistry of functional aramids properties

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