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Octakis(3-azidopropyl)octasilsesquioxane: A Versatile Nanobuilding Block for the Efficient Preparation of Highly Functionalized Cube-Octameric Polyhedral Oligosilsesquioxane Frameworks Through Click Assembly

AuthorsTrastoy, Beatriz ORCID; Pérez-Ojeda, M. Eugenia CSIC; Sastre Muñoz, Roberto CSIC; Chiara, José Luis CSIC ORCID
Click chemistry
Issue Date2010
CitationChemistry - A European Journal 16(12): 3833-3841 (2010)
AbstractA one-step synthesis of octakis(3-azidopropyl)octasilsesquioxane from commercially available octakis(3-aminopropyl)octasilsesquioxane has been developed through a highly efficient diazo-transfer reaction under very mild conditions. Nonaflyl azide is shown to be a safer, cheaper, and more efficient reagent for this transformation than the better known and generally used diazo-transfer reagent triflyl azide. Octakis(3-azidopropyl)octasilsesquioxane is an excellent nanobuilding block that can be readily octafunctionalized with a range of terminal alkynes by copper(I)-catalyzed 1,3-dipolar azide–alkyne cycloaddition to provide new functional nanocages, maintaining a perfect 3D cubic symmetry. The mildness, simplicity, and efficiency of this approach have been demonstrated in the preparation of a glyco-polyhedral oligosilsesquioxane (POSS) conjugate and a BODIPY–POSS cluster (BODIPY=boron dipyrromethene).
Description9 páginas, 1 figura, 1 esquema, 2 tablas
Publisher version (URL)http://dx.doi.org/10.1002/chem.200902422
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