Octakis(3‐azidopropyl)octasilsesquioxane: A Versatile Nanobuilding Block for the Efficient Preparation of Highly Functionalized Cube‐Octameric Polyhedral Oligosilsesquioxane Frameworks Through Click Assembly |
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Authors: | Beatriz Trastoy M Eugenia Pérez‐Ojeda Roberto Sastre Prof Dr Jose Luis Chiara Dr |
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Institution: | 1. Instituto de Química Orgánica General, CSIC, Juan de La Cierva, 3, 28006 Madrid (Spain), Fax: (+34)?91‐564‐4853;2. Instituto de Ciencia y Tecnología de Polímeros, CSIC, Juan de La Cierva, 3, 28006 Madrid (Spain) |
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Abstract: | A 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). |
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Keywords: | azides carbohydrates click chemistry dyes/pigments silsesquioxanes |
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