Functionalization of monovinyl substituted octasilsesquioxane via photochemical thiol-ene reaction

•Synthesis of functionalized monosubstituted POSS via thiol-ene reaction under UV.•More efficient synthetic strategy relative to the methods previously explored.•These new POSS would play important roles in the preparation of hybrid materials.

In this paper, monovinyl substituted POSS was chosen as the starting material to react with a series of thiols bearing hydroxyl, carboxyl, ester and trialkoxysilane groups to produce the corresponding functionalized POSS monomers in high yield via thiol-ene reaction under UV irradiation. The resulting functional cage compounds were fully characterized by FTIR, NMR, elemental analysis and mass spectroscopy. It was appeared that the thiol-ene reaction was a more efficient synthetic strategy in the preparation of functional POSS compounds relative to the methods previously explored. These cage compounds enrich the silsesquioxane pool and they would play important roles in the preparation of hybrid materials and other applications.

Graphical abstractMonovinyl substituted octasilsesquioxane reacted with various commercially available thiols bearing different functional groups (hydroxyl, carboxyl, ester and alkoxyl) to produce the corresponding functionalized monosubstituted thioether cage compounds in high yield under UV irradiation.Figure optionsDownload full-size imageDownload as PowerPoint slide