Synthesis of optically active aromatic poly(ether ketone)s containing 2,2′-bis (4-benzoylphenoxy)-1,1′-binaphthyl-6,6′-ene backbones

Maeyama, Katsuya; Maeda, Shugo; Oginö, Kazuhíde; Saito, Hiromu; Yonezawa, Noriyuki

doi:10.1016/j.reactfunctpolym.2005.06.006

Cited by 20 publications

(8 citation statements)

References 20 publications

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“…Probably, the adequate solubility is due to the suitably twisting structures between naphthalene rings of the resulting polymers, similar to reported aromatic polyketones bearing 2,2 0 -dioxy-1,1 0 -binaphthyl-6,6 0 -diyl units. [9][10][11] Glass transition temperatures (T g ) of the polymers 7a and 7b were almost as high as those of wholly aromatic polyketones containing 2,2 0 -dimethoxy-1,1 0 -binaphthylene units previously reported.…”

Section: Cyclization Of 5a With (S)-binol (1)mentioning

confidence: 63%

“…14,15,18 Next, reaction of difluoride 3 with 4-chlorobenzoic acid (4a) was carried out in P 2 O 5 -MsOH. 19 According to our previous report, 11 the reaction at 80 C afforded the corresponding disubstituted binaphthyl (5a) in good yield. Similarly, disubstituted binaphthyl 5b was also prepared in good yield (Scheme 1).…”

Section: Synthesis Of Pre-cyclized Productsmentioning

confidence: 67%

“…[4][5][6][7][8] We have also reported the syntheses of optically active aromatic polyketones bearing 2,2 0 -dioxy-1,1 0 -binaphthyl-6,6 0 -diyl units via nucleophilic aromatic substitution polymerization and nickel complex-mediated aromatic coupling polymerization. [9][10][11] The resulting polyketones have high thermal stability and excellent solubility to organic solvents such as CHCl 3 and DMF. Large dihedral angles between two naphthalene rings raise the solubility of the polyketones.…”

Section: 2mentioning

confidence: 99%

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Synthesis of Wholly Aromatic Polyketones Containing Optically Active Macrocycles

Maeyama

Maeda

Saito

et al. 2007

Polym J

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Section: Cyclization Of 5a With (S)-binol (1)mentioning

confidence: 63%

Section: Synthesis Of Pre-cyclized Productsmentioning

confidence: 67%

Section: 2mentioning

confidence: 99%

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Synthesis of Wholly Aromatic Polyketones Containing Optically Active Macrocycles

Maeyama

Maeda

Saito

et al. 2007

Polym J

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“…130,132 In the same manner, utilization of nucleophilic aromatic substitution polymerization is far more convenient method to obtain optically active aromatic polymers of aromatic poly-(ether ketone)s (Scheme 40). 133,134 The chemistry of the wholly aromatic polyketones composed of 2,2 0 -dimethoxy-1,1 0 -binaphthyl (135) will be reviewed and discussed elsewhere in the future.…”

Section: Synthesis Of Wholly Aromatic Poly-ketones Comprising Of 22mentioning

confidence: 99%

Synthesis of Wholly Aromatic Polyketones

Yonezawa

Okamoto

2009

Polym. J.

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The structural design strategy and the synthetic approaches for the wholly aromatic polyketones and the monomers are described. Electrophilic aromatic aroylation substitution polycondensation and aromatic coupling polycondensation have been investigated as synthetic routes for wholly aromatic polyketones by the author's group. Acyl-acceptant arene molecules as the electrophilic aromatic aroylation substitution polycondensation type monomers and the aromatic nuclei for bis(chlorobenzoylated) compounds as the aromatic coupling polycondensation one were designed and synthesized employing 2,2 0 -dioxybiphenyl, 2,2 0 -dioxy-1,1-binaphtyl, and o-terphenyl skeletons. Determining factors for monomers, which enable regioselective polycondensation, are also discussed. The properties of polyketones are also discussed briefly on the basis of polymer repeating unit structures. Aromatic polyketones are a group of aromatic polymers having ketonic carbonyl groups as the major linkage in the aromatic polymer main chain. Though there have been reported many examples of aromatic polyketones, almost all of them belong to the category of ''aromatic poly(ether ketone)s.'' [1][2][3][4][5] In fact, the term ''aromatic polyketone'' is generally apt to be regarded identical to ''aromatic poly(ether ketone).'' As a representative material of this category of aromatic polymer, PEEK Ò (1), a poly(ether ether ketone), is well-known super engineering plastics showing superior thermal stability, mechanical strength, and chemical resistance. Figure 1 shows the structure of PEEK Ò (1). The repeating unit of the polymer is composed of three 1,4-phenylene moieties bonded with two ether linkages and one ketonic carbonyl group. The structure suggests that PEEK Ò (1) might have properties more attributable to aromatic ether rather than aromatic ketone.On the other hand, aromatic polymers that have main chain structure composed of only aromatic rings and ketonic carbonyl groups are another type of aromatic polyketones (Figure 2). 6 The authors' group has been investigating the synthesis of aromatic polyketones free from main chain hetero linkages, wholly aromatic polyketones, during recent one and a half decades. Contrary to aromatic poly(ether ketone)s, wholly aromatic polyketones were seldom reported before.Prior to discussion of synthetic chemistry of wholly aromatic polyketones, the overview of aromatic polyketones including aromatic poly(ether ketone)s is briefly summarized to discriminate between aromatic poly(ether ketone)s and wholly aromatic polyketones.Aromatic polyketones are obliged to have copolymer structure composed of aromatic rings and ketonic carbonyl groups. From this point, aromatic polyketones are regarded as polyarylenes bearing inserted carbonyl groups. These polymers are classified into wholly aromatic polyketones or others according to the absence or presence of hetero linkages in the main chain. Aromatic poly(ether ketone) is the representative polymer of the latter type.As a natural consequence of the structural characterist...

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“…[1][2][3] In particular, poly(ether ether ketone) is well known as one of the great engineering plastics. We synthesized aromatic poly(ether ketone)s [4][5][6] and wholly aromatic polyketones 7,8 containing optically active 2,2¢-dioxy-1,1¢-binaphthyl-6,6¢-diyl units. These polymers have high chemical stability and excellent solubility in organic solvents such as CHCl 3 and DMF.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of aromatic poly(ether ketone)s bearing optically active macrocycles through Suzuki coupling polymerization

Maeyama

Yamashita

Saito

et al. 2012

Polym J

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Synthesis of optically active aromatic poly(ether ketone)s containing 2,2′-bis (4-benzoylphenoxy)-1,1′-binaphthyl-6,6′-ene backbones

Cited by 20 publications

References 20 publications

Synthesis of Wholly Aromatic Polyketones Containing Optically Active Macrocycles

Synthesis of Wholly Aromatic Polyketones Containing Optically Active Macrocycles

Synthesis of Wholly Aromatic Polyketones

Synthesis of aromatic poly(ether ketone)s bearing optically active macrocycles through Suzuki coupling polymerization

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