Electrophilic Aromatic Aroylation Polycondensation of Acyl-acceptor and Acyl-donor Molecules Composed of Binaphthylylene or Biphenylylene Aromatic Ring Assembly Units

• Published in: KOBUNSHI RONBUNSHU Vol. 66; no. 4; pp. 147 - 153
• Main Authors: OKAMOTO, Akiko, SHIKIJI, Wataru, MAEYAMA, Katsuya, OIKE, Hideaki, IMAIZUMI, Masahiro, YONEZAWA, Noriyuki
• Format: Journal Article
• Language: English; Japanese
• Published: The Society of Polymer Science, Japan 01.01.2009
• Subjects: Acidic Mediator; Acyl-acceptor Monomer; Acyl-donor Monomer; Consecutive Aroylation; Electrophilic Aromatic Aroylation; Polycondensation
• ISSN: 0386-2186; 1881-5685
• DOI: 10.1295/koron.66.147

Polymerization of 2,2′-dimethoxybiphenyl and 2,2′-dimethoxybis(1-naphthyl) as acyl-acceptor monomers and 2,2′-dimethoxybis(1-naphthylylene)-6,6′-dicarboxylic acid/-dicarbonyl chloride and 2,2′-dimethoxybiphenyl dicarboxylic acid/-dicarbonyl chloride as acyl-donor monomer in the electrophilic aromatic aroylation polycondensation is discussed. 2,2′-Dimethoxybis(1-naphthyl) only gave medium molecular weight aromatic polyketones by phosphorous pentoxide-methanesulfonic acid (P2O5-MsOH)-mediated electrophilic aromatic aroylation polycondensation with 2,2′-dimethoxybiphenyl and its dicarboxylic acid, whereas 2,2′-dimethoxybiphenyl has proved to be far more effective acyl-acceptant ability to give various aromatic polyketones with arenedicarboxylic acids/-dicarbonyl chlorides with the aid of trifluoromethanesulfonic acid (TfOH) or P2O5-MsOH. In general, the reactivity of acyl-acceptor monomer determines the susceptibility of electrophilic aromatic aroylation polycondensation. Furthermore, we could show that TfOH with arenedicarbonyl chloride has tolerable activity with sufficient selectivity and balanced reactivity, which is a requisite to promote this type of polycondensation.