Synthesis of a Polyconjugated Polymer by Aldol Condensation of 2,5-Diformylfuran and Acetone

Abstract

Pioneer synthesis of the product of aldol polycondensation between 2,5-diformylfuran and acetone is presented. The synthesis was accomplished by a direct reaction of diformylfuran and acetone in dimethyl sulfoxide with addition of aqueous sodium hydroxide as a catalyst. The fact of the aldol condensation occurrence and formation of the polyconjugated oligomers in this system is confirmed by 1H nuclear magnetic resonance and molecular absorption spectroscopy. Cannizzaro reaction plays a significant side process role in the studied system, leading to the loss of diformylfuran’s aldehyde groups and their inability to participate in polymer chain growth. A solid polymeric product of brown color was isolated with the yield of 28 % based on the initial diformylfuran. The solid product is insoluble (judging by the lack of coloration in liquid) in various tested solvents: water, 1,4-dioxane, dimethyl sulfoxide, acetone, chloroform, or 1,2-dichloroethane with trifluoroacetic acid mixed in different proportions. The presence of polyconjugated chains in the solid product is confirmed by electron spin resonance spectroscopy.