Glycidyl alkoxysilane reactivities towards simple nucleophiles in organic media for improved molecular structure definition in hybrid materials

Abstract

For hybrid materials, the relationship between the macroscopic properties and the molecular structures and dynamics at the microscopic between the organic and inorganic components level is crucial. The characterization of these components as well as their reactivity have to be emphasized in order to design and synthesize improved hybrids. We report herein the first comprehensive study of the reactivity in organic media of (3-glycidyloxypropyl)trialkoxysilanes, widely used as precursors in sol–gel hybrid synthesis, towards common nucleophiles. Thorough investigations of the reactions allowed us to draw clear conclusions about the reactivities of both epoxide and alkoxysilane functions. Furthermore, the nucleophile properties and the method of activations have a great influence on the reaction outcomes, and unexpected results were found in some cases. The importance of the nature of the alkoxy residues (methoxy, ethoxy…) was also investigated highlighting chemoselective reactions on glycidyl silane derivatives (GPTMS, GPTES and PECS) and opening a new library of original sol–gel precursors.