Synthesis and characterization of modified Schiff base silatranes (MSBS) via 'Click Silylation'

Schiff bases (1a-1d) were modified into terminal alkynes (2a-2d) which on Click Silylation with 3-azidopropyltriethoxysilane (AzPTES) yielded 1,2,3-triazole capped triethoxysilanes (3a-3d). These triethoxysilanes on transesterification with triethanolamine afforded corresponding modified Schiff base silatranes (MSBS) (4a-4d) in high yield and purity. All the synthesized compounds were well characterized by IR, NMR (H-1,C-13), mass spectroscopy, elemental analysis and complete structure elucidation by X-ray diffraction studies for 2b and 4b. Starting alkynes and final silatranes are further compared by their absorption spectra and TGA analysis. Synthesized MSBS are the first compounds of their kind which being hydrolytically stable can be put to further use in the field of medical and material research. (C) 2014 Elsevier B.V. All rights reserved.