Recent studies in the field of self-healing polymers offer a solution to the often expensive replacement of polymers or plastics. Due to its concerted and thermally reversible nature, the Diels-Alder reaction is a suitable reaction for both the synthesis of and healing pathway for self-healing polymers. This study focused on a small-molecule model for Diels-Alder polymerizations that used substituted furans as dienes. The dienes used were furan, furfuryl alcohol, 3-furylpropan-1-ol, (furanmethoxy)pentafluorobenzene (synthesized from furfuryl alcohol in 83% yield), and (furanpropoxy)pentafluorobenzene. The diene (furanpropoxy)pentafluorobenzene was synthesized from 3-(2-furyl)acrolein. This α,β-unsaturated aldehyde was hydrogenated in the presence of a Raney Nickel catalyst to form 3-(2-furyl)propan-1-ol. A higher-yielding but longer synthetic path involved NaBH4 reduction of the carbonyl followed by hydrogenation of the alkene. The resulting alcohol was then deprotonated using NaH and reacted with hexafluorobenzene in anhydrous THF to form (furanpropoxy)pentafluorobenzene. Diels-Alder kinetic experiments of each diene with N-(4-fluorophenyl)maleimide in deuterated benzene were followed by 19F NMR in order to study substituent group effects on Diels-Alder kinetics pertaining to thermal, self-healing polymers.

Synthesis of furan derivatives and the kinetics of their Diels-Alder reactions with N-(4-fluorophenyl) maleimide

253rd National Meeting (2017)

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