A Synthetic Route to Quaternary Pyridinium Salt-Functionalized Silsesquioxanes
A synthetic route to potentially biocidal silsesquioxanes functionalized by quaternary pyridinium functionalities has been developed.N-Alkylation reactions of the precursor compounds 4-(2-(trimethoxysilyl)ethyl)-pyridine (5) and 4-(2-trichloro-silylethyl)pyridine (6) with iodomethane,n-hexylbromide, andn-hexadecylbromide cleanly afforded the correspondingN-alkylpyridinium salts (7–10). The synthesis of a 4-(2-ethyl)pyridine POSS derivative (2) was achieved by capping of the silsesquioxane trisilanol Cy7Si7O9(OH)3(1) via two different preparative routes. Attempts to use compound2as precursor for quaternary pyridinium salt-functionalized POSS derivatives were met with only partial success. Only the reaction with iodomethane cleanly afforded the newN-methylpyridinium salt12in high yield, whereasn-hexylbromide andn-hexadecylbromide failed to react with2even under forcing conditions.