The preparation, reactivity, and synthetic applications of functionalized perfluorooctynyl and fluorooctenyl silanes were explored. Fluorinated compounds are unique that they are water and oil repellant, lubricative, combustible, and chemically inert. Fluorinated silsesquioxanes have attracted considerable attention from material scientists as they provide nano-scaffolds for the fluoroalkyl groups. One route to perfluorinated silsesquioxanes is via condensation of an alkynyltrialkoxysilane or alkynyltrihalosilane. In this work, a perfluorinated alkylnyl silane monomer represented by the formula, RfSiX3 [Rf - perfluorooctynyl group, X = OC2H5] was synthesized in ~50% yield by nucleophillic addition of 1-perfluorooctynyl magnesium bromide with commercially available alkoxy silane electrophiles. Unfortunately, acid hydrolysis leads to an ill defined silsesquioxane mixture. Therefore, an alternate route was pursued using a fluorooctenyl silane. The unsaturated C=C double bond also provides an possible site of reactivity which could be used to attach the fluoro-POSS to surfaces. The synthesis of functionalized fluorooctenyl silane and its condensation will be discussed.

Perfluorinated and partially fluorinated silane derivatives of perfluorooctynes: Synthesis, characterization, and chemical reactivity

243rd National Meeting (2012)

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