Superacid-catalyzed polycondensation of acenaphthenequinone with aromatic hydrocarbons

Mikhail G. Zolotukhin, Serguei Fomine, Luz María Lazo, Roberto Salcedo, Luis E. Sansores, Gerardo G. Cedillo, Howard M. Colquhoun, Juan M. Fernandez-G., Alexei F. Khalizov

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

Abstract

A novel series of linear, high molecular weight polymers were synthesized by one-pot, superacid-catalyzed reaction of acenaphthenequinone (1) with aromatic hydrocarbons. The reactions were performed at room temperature in the Brønsted superacid CF3SO3H (trifluoromethanesulfonic acid, TFSA) and in a mixture of TFSA with methanesulfonic acid (MSA) and trifluoroacetic acid (TFA), which was used as both solvent and a medium for generation of electrophilic species from acenaphthenequinone. The polymer-forming reaction was found to be dependent greatly on the acidity of the reaction medium, as judged from the viscosity of the polymers obtained. Polycondensations of acenaphthenequinone with 4,4′-diphenoxybenzophenone (f), 1,3-bis(4-phenoxybenzoyl)benzene (g), 1,4-bis(4-phenoxybenzoyl)benzene (h), 1,10-bis(4-phenoxyphenyl)decane-1,10-dione (i), 2,6-diphenoxybenzonitrile (j), 2,6-diphenoxybenzoic acid (k), and 2-(4-biphenylyl)-6-phenylbenzoxazole (I) proceeded in a reaction medium of wide range of acidity, including pure TFSA (Hammett acidity function H0 of pure TFSA is -14.1), whereas condensation of 1 with biphenyl, terphenyl, diphenyl ether, and 1,4-diphenoxybenzene needed a reaction medium of acidity H0 less than -11.5. A possible reaction mechanism is suggested. The polymers obtained were found to be soluble in the common organic solvents, and flexible transparent films could be cast from the solutions. 1H and 13C NMR analyses of the polymers synthesized revealed their linear, highly regular structure. The polymers also possess high thermostability. Char yields for polymers 3a, 3c, 3d, and 3l in nitrogen were close to 80% at 1000°C.

Original languageEnglish (US)
Pages (from-to)6005-6014
Number of pages10
JournalMacromolecules
Volume38
Issue number14
DOIs
StatePublished - Jul 12 2005
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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