A convenient and scalable (gram-scale) route to unprecedented T8D2-DDSQs bearing four chloro-(3b) or four azido (5b) groups is reported. Both compounds were characterized and proved to undergo successfully nucleophilic substitution for 3b (with iodide or azide) and coppercatalyzed azide-alkyne [3+2] cycloaddition for 5b. All these transformations occurred under mild conditions and the corresponding DDSQs were prepared in very high yields. Beyond the enhanced multivalency as compared to the previously described di-substituted D2T8 structures, the reported tetra-functional DDSQs are formed as a single isomer and readily isolated in very high yields.Moreover, the tetra-azido DDSQ 5b constitutes a multipurpose nano-building block for the further preparation of new inorganic-organic hybrid materials where the covalent incorporation of a DDSQ moiety brings valuable properties.
Tetra(3-mercaptopropyl)-silsesquioxanes with double-decker (DDSQ) or ladder nano-cores were easily prepared from the corresponding tetraallyl derivatives through fast and convenient thiol-ene reaction. An additional tetrathiol-DDSQ with more flexible arms was also...
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