The Diels-Alder (DA) reaction has been the subject of renewed interest in the field of self-healing polymers because the DA reaction can be thermo-reversible within a moderate temperature window.  This research focuses on the synthesis of highly-fluorinated dienes for use in the Diels-Alder reaction. Nucleophilic substitution reactions of furfuryl alcohol with decafluorobiphenyl under basic conditions afforded either 1-(furanmethoxy)nonafluorobiphenyl in a 62% yield or 4,4’-bis(furanmethoxy)octafluorobiphenyl in a 78% yield, depending on the reactant stoichiometry and reaction conditions  Diels-Alder reactions of these dienes with N-4-fluorophenylmaleimide were studied as models for the synthesis of linear DA polymers based on bis(maleimide) monomers. Reaction products were purified using chromatographic methods and characterized using <sup>1</sup>H and <sup>19</sup>F NMR spectroscopy.

Self-healing polymers: Synthesis of highly-fluorinated dienes and their model Diels-Alder reactions

249th National Meeting (2015)

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