| Summary: | Herein, we report synthetic strategies for the development of a bifunctional Janus T<sub>4</sub> tetrapod (Janus ring), in which the orthogonal silsesquioxane and organic faces are independently functionalized. An all-<i>cis</i> T<sub>4</sub> tetrasilanolate was functionalized to introduce thiol moieties on the silsesquioxane face and naphthyl groups on the organic face to introduce luminescent and self-organization properties. The stepwise synthesis conditions required to prepare such perfectly defined oligomers via a suite of well-defined intermediates and to avoid polymerization or reactions over all eight positions of the tetrapod are explored via <sup>29</sup>Si, <sup>13</sup>C and <sup>1</sup>H NMR, FTIR and TOF-ESI mass spectroscopy. To the best of our knowledge, this is one of the few reports of Janus T<sub>4</sub> tetrapods, with different functional groups located on both faces of the molecule, thus expanding the potential range of applications for these versatile precursors.
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