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

Okamoto, Akiko; Mitsui, Ryosuke; Maeyama, Katsuya; Saito, Hiromu; Oike, Hideaki; Murakami, Yoshihiko; Yonezawa, Noriyuki

doi:10.1016/j.reactfunctpolym.2007.08.003

Cited by 7 publications

(7 citation statements)

References 32 publications

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“…To synthesise SCT-SAPs via the strategy of 'sulfonation before polymerisation', the first goal is to search for suitable side-chainionized aromatic monomers. When looking through such a rich library of dicarboxylic acid and diarene monomers established by a pioneering research on polyacylation (see Table S1, ESI †), [15][16][17][18][19][20] inspiration hits us that the etherification of 2,2 0 -dihydroxybiphenyl with ionic group-terminated alkyl substituents (-R-IG) would create a series of novel ionised monomers as shown in Scheme 1a, where the length and property (fluorinated or not) of R and the species of IG could be facilely and widely varied.…”

Section: Synthesis and Characterisation Of Sulfonated Monomer And Pol...mentioning

confidence: 99%

“…Polyacylation of dicarboxylic acid monomers and electronrich diarene monomers or self-polyacylation of monomers containing both a carboxylic acid and an electron-rich arene group in acidic media such as P 2 O 5 -polyphosphoric acid mixture (P 2 O 5 -PPA), 15 P 2 O 5 -CH 3 SO 3 H mixture (PPMA) [16][17][18][19] and CF 3 SO 3 H (TFSA) 20 has been well developed for the synthesis of aromatic polyketones. However, as far as we know, no literature on the synthesis of SCT-SAPs directly from ionised monomers in such a polymerisation system has been reported.…”

Section: Introductionmentioning

confidence: 99%

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Novel aromatic proton-exchange polyelectrolytes via polyacylation of pre-sulfonated monomers

Zhang

2012

J. Mater. Chem.

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Section: Synthesis and Characterisation Of Sulfonated Monomer And Pol...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Novel aromatic proton-exchange polyelectrolytes via polyacylation of pre-sulfonated monomers

Zhang

2012

J. Mater. Chem.

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“…4-Bromodiphenyl ether (2), 4-fluorobenzoic acid and 4,4¢-oxybiphenol (8) were purchased from Tokyo Kasei Kogyo (Tokyo, Japan). Aluminum chloride, potassium carbonate and pinacol were purchased from Wako Pure Chemical Industries (Osaka, Japan).…”

Section: Experimental Procedures Materialsmentioning

confidence: 99%

“…[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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“…As briefly concerned above, introduction of 2,2 0 -dimethoxy-1,1 0 -binaphthylylene unit into aromatic polyketones has been performed efficiently via regioselective electrophilic aromatic aroylation introduction of polymerizable functional groups into 2,2 0 -dimethoxy-1,1 0 -binaphthyl nuclei (135) followed by suitable polymerization such as transition metal complex aromatic coupling polycondensation (Scheme 37) and electrophilic aromatic aroylation polycondensation (Schemes 38, 39). 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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Electrophilic aromatic aroylation polycondensation synthesis of wholly aromatic polyketone composed of 2,2′-dimethoxy-1,1′-binaphthylylene moiety

Cited by 7 publications

References 32 publications

Novel aromatic proton-exchange polyelectrolytes via polyacylation of pre-sulfonated monomers

Novel aromatic proton-exchange polyelectrolytes via polyacylation of pre-sulfonated monomers

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

Synthesis of Wholly Aromatic Polyketones

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