Self-healing polymers have been studied, because these polymers, when damaged, are more easily repaired in situ. This project examines a model for a thermal self-healing polymer, which requires a heat source to effect its repair. The starting materials of the Diels-Alder models were synthesized, and the equilibrium constants for the reactions were determined by integrating 19F NMR spectra. The dienophile used, N-(4-fluorophenyl) maleimide (48% yield), has two EWGs making it highly reactive. The dienes used were furan, furfuryl alcohol, 3-furylpropan-1-ol, (furanmethoxy)pentafluorobenzene (synthesized from furfuryl alcohol in 83% yield), and (furanpropoxy)pentafluorobenzene. The equilibrium constants were measured at temperatures from 25°C to 65°C. For each reaction, K decreased as T increased. The extent of K depended on the electron-donating or electron-withdrawing nature of the furan substituents.

Equilibrium constants in the Diels-Alder reactions of furan derivatives with N-(4-fluorophenyl) maleimide

253rd National Meeting (2017)

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