Synthesis and characterization of a novel AB2 monomer and corresponding hyperbranched poly(arylene ether phosphine oxide)s

Qin, Lin; Long, Timothy Edward

doi:10.1002/1099-0518(20001015)38:20<3736::aid-pola40>3.0.co;2-y

Cited by 63 publications

(53 citation statements)

References 20 publications

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“…phenyl quinoxaline)s, [16][17][18] poly(phenylene oxide)s, [19,20] poly(arylene ether imide)s, [21][22][23] poly(arylene ether ketone imide)s, [24,25] and poly(arylene ether phosphine oxide)s. [26,27] However, AB x monomers are usually not always commercially available and their synthesis sometimes involves multistep organic synthesis. As a consequence several groups have attempted a facile A 2 þ B 3 approach toward hyperbranched polymers.…”

Section: Introductionmentioning

confidence: 59%

Synthesis and Characterization of Hyperbranched Poly(arylene ether)s from a New Activated Trifluoro B₃ Monomer Adopting an A₂ + B₃ Approach

Banerjee

Komber

Häußler

et al. 2009

Macro Chemistry & Physics

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A new trifluoromethyl‐activated trifluoro monomer was successfully prepared by Pd‐initiated coupling of 1,3,5‐tribromobenzene with 4‐fluoro‐3‐trifluoromethylphenylboronic acid. 1,3,5‐Tris(4‐fluoro‐3‐trifluoromethylphenyl)benzene (B3) leads to several hyperbranched poly(arylene ether)s when reacted with three different bisphenols (A2) in different molar ratios. The 1.5:1 molar product of A2/B3 showed very high molecular weight without significant gelation. The products have been well characterized by GPC, DSC, TGA, FTIR, and NMR techniques. The 19F NMR signals were used to calculate the degree of branching. The 1.5:1 molar products have excellent thermal stability and higher glass transition temperatures than their linear analogs.magnified image

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Section: Introductionmentioning

confidence: 59%

Synthesis and Characterization of Hyperbranched Poly(arylene ether)s from a New Activated Trifluoro B₃ Monomer Adopting an A₂ + B₃ Approach

Banerjee

Komber

Häußler

et al. 2009

Macro Chemistry & Physics

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“…1 In addition to common electron-withdrawing groups such as sulfone and ketone, certain heterocycles can activate aryl halides toward aromatic nucleophilic substitution. Several hyperbranched poly(arylene ether)s from AB 2 monomers have been reported in the literature that include poly(ether sulfone), 12 poly(ether ketone)s, [14][15][16] poly(etheroxazole), 18 poly(ether phenyl phenyl quinoxaline)s, [19][20][21] poly(phenylene oxide)s, 22,23 poly-(arylene ether imide)s, [24][25][26] poly(arylene ether ketone imide)s, 27,28 and poly(arylene ether phosphine oxide)s. 29,30 Increasingly, hyperbranched polymers are synthesized also by the A 2 þ B y approach from easily available monomers. Several groups have attempted a facile A 2 þ B 3 approach toward hyperbranched polymers.…”

Section: Introductionmentioning

confidence: 99%

Extremely High Molar Mass Hyperbranched Poly(arylene ether)s from a New Semifluorinated AB₂ Monomer by an Unusual AB₂+ A₂ Polymerization Approach

et al. 2010

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A new AB 2 monomer [3,5-bis(4-fluoro-3-trifluoromethylphenyl)phenol] has been successfully prepared by the Pd(0)-initiated coupling reaction of 4-fluoro-3-trifluoromethylphenylboronic acid and 3,5-dibromophenol. This monomer led to a high molecular weight hyperbranched polymer (M w =230 000 g/mol) by self-condensation. Several hyperbranched polymers have also been prepared successfully by condensing the AB 2 monomer with different diphenols (A 2 ) in different molar ratios. Here, the stoichiometric (2:1) AB 2 /A 2 products 2c and 3c showed extremely high weight-average molecular weights of 3 730 000 and 4 470 000 g/mol without any gelation under the specified reaction conditions. The products have been well characterized by SEC, DSC, TGA, FTIR, and NMR techniques. The degree of branching of the AB 2 product could be determined by proton NMR for a medium molar mass sample and was found to be 0.5. The AB 2 selfcondensed hyperbranched poly(arylene ether) showed a glass transition temperature (T g ) as high as 199°C and the 10% weight loss temperature as high as 573°C in N 2 , whereas the extremely high molar mass products 2c and 3c of the AB 2 /A 2 approach did not show a T g up to 350°C and similar high thermal stability. Homogenous and stable films could be prepared from these new polymers which are prone to self-crosslinking by heating especially for the AB 2 /A 2 products. High hydrophobicity of the polymers combined with high thermal stability renders those materials highly interesting for microelectronics application.

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“…[1][2][3] For example, hyperbranched polymers exhibit several unique properties, including low solution and melt viscosities, enhanced solubility, and the presence of a large number of functional end groups for further modification [4][5][6][7][8][9][10][11][12][13][14][15][16][17] as compared to linear analogs. However, the application of hyperbranched polymers as conventional structural materials is limited due to inadequate mechanical strength, which is attributed to a lack of chain entanglements among the low molar mass branches.…”

Section: Introductionmentioning

confidence: 99%

Highly Branched Poly(arylene ether)s via Oligomeric A₂ + B₃ Strategies

Qin¹,

Ünal

Fornof

et al. 2006

Macro Chemistry & Physics

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Summary: Branched poly(arylene ether)s were prepared in an oligomeric A2 + B3 polymerization of phenol endcapped telechelic poly(arylene ether sulfone) oligomers as A2 and TFPPO as trifunctional monomer B3. The molar mass of the A2 oligomer significantly influenced the onset of gelation and the DB. A high level of cyclization during polymerization of low molar mass A2 oligomers (U3 = 660 and U6 = 1 200 g · mol−1) led to a high conversion of functional groups in the absence of gelation, and the level of cyclization reactions in the polymerization decreased as the molar mass of the A2 oligomer was increased. The pronounced steric effect in the polymerization of higher molar mass A2 oligomers (U8 = 1 800 and U16 = 3 400 g · mol−1) resulted in low reactivity of the third aryl fluoride in the B3 monomer. As a result, only slightly branched (U8 = 1 800 g · mol−1) or nearly linear (U16 = 3 400 g · mol−1) high molar mass products were obtained with higher molar mass A2 oligomers. The branched polymers exhibited lower Mark‐Houwink exponents and [η] relative to linear analogs, and differences between the branched polymers and linear analogs were less significant as the molar mass of the A2 oligomers was increased due to a decrease in the overall DB. magnified image

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Synthesis and characterization of a novel AB2 monomer and corresponding hyperbranched poly(arylene ether phosphine oxide)s

Cited by 63 publications

References 20 publications

Synthesis and Characterization of Hyperbranched Poly(arylene ether)s from a New Activated Trifluoro B₃ Monomer Adopting an A₂ + B₃ Approach

Synthesis and Characterization of Hyperbranched Poly(arylene ether)s from a New Activated Trifluoro B₃ Monomer Adopting an A₂ + B₃ Approach

Extremely High Molar Mass Hyperbranched Poly(arylene ether)s from a New Semifluorinated AB₂ Monomer by an Unusual AB₂+ A₂ Polymerization Approach

Highly Branched Poly(arylene ether)s via Oligomeric A₂ + B₃ Strategies

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Synthesis and characterization of a novel AB2 monomer and corresponding hyperbranched poly(arylene ether phosphine oxide)s

Cited by 63 publications

References 20 publications

Synthesis and Characterization of Hyperbranched Poly(arylene ether)s from a New Activated Trifluoro B3 Monomer Adopting an A2 + B3 Approach

Synthesis and Characterization of Hyperbranched Poly(arylene ether)s from a New Activated Trifluoro B3 Monomer Adopting an A2 + B3 Approach

Extremely High Molar Mass Hyperbranched Poly(arylene ether)s from a New Semifluorinated AB2 Monomer by an Unusual AB2 + A2 Polymerization Approach

Highly Branched Poly(arylene ether)s via Oligomeric A2 + B3 Strategies

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Synthesis and Characterization of Hyperbranched Poly(arylene ether)s from a New Activated Trifluoro B₃ Monomer Adopting an A₂ + B₃ Approach

Synthesis and Characterization of Hyperbranched Poly(arylene ether)s from a New Activated Trifluoro B₃ Monomer Adopting an A₂ + B₃ Approach

Extremely High Molar Mass Hyperbranched Poly(arylene ether)s from a New Semifluorinated AB₂ Monomer by an Unusual AB₂+ A₂ Polymerization Approach

Highly Branched Poly(arylene ether)s via Oligomeric A₂ + B₃ Strategies