A Novel Approach to the Synthesis of High Performance and Functional Polymers

A novel series of linear, high molecular weight high performance and functional polymers were synthesized by a one-pot, superacid-catalyzed polyhydroxylakylation reaction of carbonyl compounds containing electron-withdrawing substituents, adjacent or relatively close to a carbocation center with non-activated aromatic hydrocarbons. The reactions were performed at room temperature in the Brønsted superacid CF3SO3H (trifluoromethanesulfonic acid, TFSA) and in a mixture of TFSA with methylene chloride, which was used as both solvent and a medium for generation of electrophilic species from the carbonyl component. Polycondensations of 1,1,1-trifluoroacetone, 2,2,2-trifluoroacetohenone, 2,7-dinitrofluorenone, acenaphthenequinone and isatin with aromatic hydrocarbons proceed readily in the presence of superacid at room temperature. 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.