TfOH-mediated electrophilic aromatic aroylation polycondensation of 2,2′-bis[4-(trifluoromethylated aroyl)phenoxy]biphenyls with arenedicarbonyl dichlorides

Okamoto, Akiko; Yamazaki, Megumi; Maeyama, Katsuya; Oike, Hideaki; Saito, Hiromu; Murakami, Yoshihiko; Yonezawa, Noriyuki

doi:10.1016/j.reactfunctpolym.2007.08.001

Cited by 6 publications

(2 citation statements)

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“…As the bifunctional acyl-acceptant monomer or the monomer precursor, 2,2 (117), and m-terphenyl were employed.…”

Section: Bifunctional Acyl-acceptant Moleculesmentioning

confidence: 99%

“…As the o-hydrogen atoms to the bridgehead carbons of biphenylylene unit sterically repel to each other, the phenylene rings are expected to have screwed conformation. In this course, the terminal phenyl groups of the o-terphenyl (117) should take the similar space position with that of 2,2 0 -dimethoxybiphenyl (7). Furthermore, this unit is expected to play a role of crankshaft unit suppressing regular aggregation of the polymer chains.…”

Section: Synthesis Of Wholly Aromatic Poly-ketones Bearing Terphenylymentioning

confidence: 99%

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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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“…As the bifunctional acyl-acceptant monomer or the monomer precursor, 2,2 (117), and m-terphenyl were employed.…”

Section: Bifunctional Acyl-acceptant Moleculesmentioning

confidence: 99%

Section: Synthesis Of Wholly Aromatic Poly-ketones Bearing Terphenylymentioning

confidence: 99%

Synthesis of Wholly Aromatic Polyketones

Yonezawa

Okamoto

2009

Polym. J.

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Electrophilic aromatic aroylation polycondensation synthesis of wholly aromatic polyketone composed of 2,2′-dimethoxy-1,1′-binaphthylylene moiety

Okamoto

Mitsui

Maeyama

et al. 2007

Reactive and Functional Polymers

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Reversible ArSE Aroylation of Naphthalene Derivatives

Okamoto

Yonezawa

2009

Chemistry Letters

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Reversible ArSE aroylation has been observed in the reaction of 2,7-dimethoxynaphthalene (1) with 4-chlorobenzoic acid/acid chloride 2 with the aid of discrete acidic mediators. The reaction readily gives 1-aroylated-, 3-aroylated-, and 1,8-diaroylated products. The product distribution clearly shows dependence on the kind and strength of the acidic mediators and the time-course of the distribution manifests dearoylation of the productive aroylnaphthalenes. These reaction behaviors including acid-strength-dependent reversibility are well interpreted from the viewpoint of highly congested noncoplanar geometry of the polyaromatic ketone products.

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TfOH-mediated electrophilic aromatic aroylation polycondensation of 2,2′-bis[4-(trifluoromethylated aroyl)phenoxy]biphenyls with arenedicarbonyl dichlorides

Cited by 6 publications

References 36 publications

Synthesis of Wholly Aromatic Polyketones

Synthesis of Wholly Aromatic Polyketones

Electrophilic aromatic aroylation polycondensation synthesis of wholly aromatic polyketone composed of 2,2′-dimethoxy-1,1′-binaphthylylene moiety

Reversible ArSE Aroylation of Naphthalene Derivatives

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