Synthesis and characterization of octakis(3-propyl ethanethioate) octasilsesquioxane

Abstract

A novel octakis(3-propyl ethanethioate)octasilsesquioxane was successfully synthesized via nucleophilic substitution on octakis(3-chloropropyl) octasilsesquioxane using potassium thioacetate in aprotic dimethylformamide as a solvent. Complete substitution proceeded at room temperature within a day to produce a crystalline product in high yield. The reaction products were characterized by 1 H, 13 C, and 29 Si NMR spectroscopy; ESI-MS; and single-crystal X-ray diffraction, confirming the structure of the cubic T 8 cage and demonstrating that the substitution reaction on eight side chains progressed smoothly under ambient conditions without any cage rearrangement or cage decomposition. © 2011 American Chemical Society.