Perfluorinated and Partially-Fluorinated Silane Derivatives of Perfluorooctyne: Synthesis Characterization and Chemical Reactivity
AIR FORCE RESEARCH LAB EDWARDS AFB CA PROPULSION DIRECTORATE SPACE AND MISSILE PROPULSION DIV/PROPULSION MATERIALS APPLICATIONS BRANCH
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The preparation, reactivity, and synthetic applications of functionalized perfluorooctynyl and fluorooctenyl silanes were explored. Fluorinated compounds are unique in that they are water and oil repellent, lubricative, incombustible, 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 alkynyl silane monomer represented by the formula RfSiX3 Rf perfluorooctyne group, X OC2H5 was synthesized in 50 yield by nucleophilic addition of 1-perfluorooctynyl magnesium bromide with commercially available alkoxysilane electophiles. Unfortunately, acid hydrolysis leads to an ill-defined silsesquioxane mixture. Therefore, an alternative route was pursued using a fluorooctenyl silane. The unsaturated C-C double bond also provides a possible site of reactivity which could be used to attach the fluoro-POSS to surfaces, thereby increasing its durability. The synthesis of functionalized fluorooctenyl silane and its condensation reactions will be discussed.
- Inorganic Chemistry