Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 12, Pages 3833-3841Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200902422
Keywords
azides; carbohydrates; click chemistry; dyes/pigments; silsesquioxanes
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Funding
- Ministry of Education and Science of Spain [CTQ-2006-15515-C02-02/BQU, MAT-2007-65778-C02-01]
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A one-step synthesis of octakis(3-azidopropyl)octasilsesquioxane from commercially available octakis(3-aminopropyl)octasilsesquioxime 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-azidopropypoyl)octasilses-quioxane is an excellent nanobuildmg 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)
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