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Superacid-catalyzed polycondensation of acenaphthenequinone with aromatic hydrocarbons

Zolotukhin, M.G., Fomine, S., Lazo, L.M., Salcedo, R., Sansores, L.E. and Cedillo, G.G. (2005) Superacid-catalyzed polycondensation of acenaphthenequinone with aromatic hydrocarbons. Macromolecules, 38 (14). pp. 6005-6014. ISSN 0024-9297

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To link to this item DOI: 10.1021/ma0503460

Abstract/Summary

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 Bronsted 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), 2,6-diphenoxybenzoic acid (k), and 2-(4-biphenylyl)-6-phenylbenzoxazole (1) proceeded in a reaction medium of wide range of acidity, including pure TFSA (Hammett acidity function H-0 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 H-0 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. H-1 and C-13 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 degrees C.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:11731
Uncontrolled Keywords:FRIEDEL-CRAFTS REACTIONS, TRIFLUOROMETHANESULFONIC ACID, PRECIPITATION, POLYCONDENSATION, POLYMER CHEMISTRY, SUPERELECTROPHILES, DERIVATIVES, POLY(PHTHALIDYLIDENEARYLENE)S, POLYETHERKETONES, ELECTROPHILES, CONDENSATION

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