Silane meets click chemistry: towards the functionalization of wet bacterial cellulose sheets

The modification of cellulosic materials is of great interest in materials research. Wet bacterial cellulose sheets were modified by an alkoxysilane under mild conditions to make them accessible to click chemistry derivatization. For this purpose (3-azidopropyl)triethoxysilane was grafted covalently onto the cellulosic surface. The silanized bacterial cellulose sheets were characterized comprehensively by attenuated total reflectance FTIR spectroscopy, solid-state NMR spectroscopy, thermogravimetric analysis, SEM with energy-dispersive X-ray spectroscopy, and elemental analysis. To demonstrate subsequent click chemistry functionalization, a new fluorophore based on fluorescein was synthesized and clicked to the silane-modified bacterial cellulose. The new method renders bacterial cellulose and other never-dried cellulosic materials susceptible to direct and facile functionalization in an aqueous medium without the need to work in water-free organic phases or to employ extensive protecting group chemistry and functional group interconversion.