Perfluoropyridine as a Scaffold for Semifluorinated Thiol-ene Networks with Readily Tunable Thermal Properties

Two new trifunctional alkene monomers based on the highly modular perfluoropyridine scaffold are synthesized with an aliphatic and an aromatic moiety, 4-penten-1-ol and eugenol, respectively. The monomers are the basis for thiol-ene thermoset materials, formulated against a difunctional or trifunctional thiol. Systems based on these novel monomers have a wide range of thermal properties, with glass transition temperatures (T(g)s) spanning from -42 to 21 degrees C. Mixed systems obey the Fox equation, and T(g)s of the mixtures can be tuned to specific values in that range. Thermal degradation temperatures follow a similar trend, with decomposition temperatures ranging from 274 to 348 degrees C in nitrogen with varying compositions having tailorability therein. This new class of semifluorinated thermoset materials with tunable thermal properties has several potential applications within the aerospace industry, such as sealants and coatings, where stability and survivability at high temperatures in harsh environmental conditions are imperative.