Synthesis of nitrile and benzoyl substituted poly(biphenylene oxide)s via nitro displacement reaction

In, Insik; Kim, Sang Youl

doi:10.1016/j.polymer.2006.04.052

Cited by 8 publications

(1 citation statement)

References 22 publications

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“…In previous work, we found that trifluoromethyl groups and ether linkages are stable in a nitro displacement reaction, even at 190 °C, and that the displacement reaction occurs quantitatively without side reactions that are frequently observed during the nitro displacement reactions at high temperatures due to the reactive nitrite ion byproduct. − …”

Section: Introductionmentioning

confidence: 91%

Poly(arylene ether)s with Low Refractive Indices: Poly(biphenylene oxide)s with Trifluoromethyl Pendant Groups via a Meta-Activated Nitro Displacement Reaction

Kim

Chung

et al. 2012

Macromolecules

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High-molecular-weight poly(biphenylene oxide)s (PBPO) were prepared from AB-type monomers, 4′(3′)hydroxy-4-nitro-2,6-bis(trifluoromethyl)biphenyl, through a meta-activated nitro displacement reaction. The displacement of nitro leaving group activated by the two trifluoromethyl groups at the meta-position produced high-molecular-weight polymers, which implies that nucleophilic aromatic substitution reaction of the nitro leaving group proceeded very effectively with two activating groups at the meta-position. The obtained polymers have weight-average molecular weight of 20 800−143 300 g/mol and molecular weight distribution of 1.68−2.85. While two homopolymers of 4′-or 3′-hydroxy-4-nitro-2,6-bis(trifluoromethyl)biphenyl, p-PBPO and m-PBPO, showed a semicrystalline morphology, copolymers of the two monomers were amorphous and dissolved in a wide range of organic solvents. The PBPOs possessed a high glass transition temperature (T g ) in the range of 169 to 208 °C depending on their structure and high thermal stability with 10% weight loss temperatures from 486 to 542 °C in nitrogen and from 465 to 516 °C in air. Moreover, PBPOs containing two trifluoromethyl groups showed low refractive indices in the range of 1.4979−1.5052 as well as low birefringence values of 0.0095−0.0148.

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Section: Introductionmentioning

confidence: 91%

Poly(arylene ether)s with Low Refractive Indices: Poly(biphenylene oxide)s with Trifluoromethyl Pendant Groups via a Meta-Activated Nitro Displacement Reaction

Kim

Chung

et al. 2012

Macromolecules

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Synthetic Aspects of Intermolecular S_NAr Reactions

Terrier

2013

Modern Nucleophilic Aromatic Substitution

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Ethoxylation of p-Fluoronitrobenzene using phase-transfer catalysts under microflow conditions

2019

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Synthesis of nitrile and benzoyl substituted poly(biphenylene oxide)s via nitro displacement reaction

Cited by 8 publications

References 22 publications

Poly(arylene ether)s with Low Refractive Indices: Poly(biphenylene oxide)s with Trifluoromethyl Pendant Groups via a Meta-Activated Nitro Displacement Reaction

Poly(arylene ether)s with Low Refractive Indices: Poly(biphenylene oxide)s with Trifluoromethyl Pendant Groups via a Meta-Activated Nitro Displacement Reaction

Synthetic Aspects of Intermolecular S_NAr Reactions

Ethoxylation of p-Fluoronitrobenzene using phase-transfer catalysts under microflow conditions

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Synthesis of nitrile and benzoyl substituted poly(biphenylene oxide)s via nitro displacement reaction

Cited by 8 publications

References 22 publications

Poly(arylene ether)s with Low Refractive Indices: Poly(biphenylene oxide)s with Trifluoromethyl Pendant Groups via a Meta-Activated Nitro Displacement Reaction

Poly(arylene ether)s with Low Refractive Indices: Poly(biphenylene oxide)s with Trifluoromethyl Pendant Groups via a Meta-Activated Nitro Displacement Reaction

Synthetic Aspects of Intermolecular SNAr Reactions

Ethoxylation of p-Fluoronitrobenzene using phase-transfer catalysts under microflow conditions

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Synthetic Aspects of Intermolecular S_NAr Reactions