Organic-Inorganic Nano-Building Blocks via Hydrogermylation of Fatty Compounds

The synthesis and characterisation of new germylated fatty acid methyl esters and fatty alcohols as novel precursors for structured dendritic materials are described. Hydrogermylation of terminal and internal C=C double bonds by arylgermanes occurred under radical initiation using azo-bis-isobutyronitrile (AIBN) and peroxides. The reactivity depends essentially on the double bond position of the fatty derivatives (intern versus extern), the size of the arylgermane and the sensitivity of the Ge-H bond to radical initiators. More challenging hydrogermylation was also performed starting from glyceryl trioleate affording the functionalised germylated triacylglyceride in quantitative yield. In aqueous polar and non-polar solvents, the germylated di- and tri-esters and their alcohol analogues self-assembled into functional nano- and microstructures (nanoparticles, micrometer spheres and lamellar forms). These structures might provide a strategy toward nanostructured materials having bio-mimetic functions or drug delivery applications.