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Synthesis of functional cubes from octavinylsilsesquioxane (OVS)

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Ge Cheng, Nicolas R. Vautravers, Russell E. Morris, David John Cole-Hamilton

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Octavinylsilsesquioxane, (CH2CH)(8)Si8O12, a cubic molecule with vinyl groups at each vertex, has been elaborated to give a series of potential starting materials for nanohybrid synthesis. Terminal bromophenyl groups were introduced onto the surface of octavinylsilsesquioxane either by cross-metathesis or hydrosilylation to give fully bromide substituted POSS A, POSS B and POSS C; the last two were further capped with trimethylsilylacetylene by Sonogashira coupling to produce POSS D and POSS E, showing interesting potential for more useful end group functionalisation. Heck coupling with iodobenzene was used to make the simple phenyl terminated dendrimer POSS F. Cross-metathesis of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) styrene with octavinylsilsesquioxane afforded POSS G with eight aryl borate groups on its periphery, suitable for use as a starting material in Suzuki coupling. Finally, POSS H has been functionalized with 8 benzyl chloride groups via Grubbs coupling, allowing further substitutions by nucleophiles.



Original languageEnglish
Pages (from-to)4662-4667
Number of pages6
JournalOrganic & Biomolecular Chemistry
Issue number24
Publication statusPublished - 2008

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