Dottorato in SCIENZE CHIMICHE

Titolo della tesi: Synthesis, characterization and application of new amphiphilic compounds as precursors of functional materials

In the last two decades or so, bile acids and their synthetic derivatives have been shown to be useful building blocks in the preparation of particular nanostructures in a bottom-up approach. This work is part of that research field and focused on the preparation of new derivatives of bile acids and on the study of their properties that make them versatile in a wide range of research field, from medicinal chemistry and catalysis to surface chemistry and molecular electronics. In particular, this research work dealt with the synthesis of new aromatic derivatives through click reactions, an innovative synthetic method never described in literature to link aromatic subunits to bile acids, in order to evaluate their aggregation properties and the possibility of exploiting this functionalization method on this type of substrate. This is what will be shown in Chapter 2. In Chapter 3, bile acids were then tested also as useful surfactants essential for amino acids catalytic activity carried out in only water. Furthermore, in Chapter 4, from the positive data of the aforementioned tests arose the idea of directly functionalizing these amphiphilic molecules with amino acid subunits, also evaluating if this could give a greater contribution by increasing yields, diastereoisomeric and enantiomeric excesses, given the intrinsic characteristics of molecules capable of inducing greater stereoselectivity. Finally, ferrocenyl derivatives were synthesized, connecting the subunits in C-3 position or on steroid skeleton side chain in order to obtain molecules capable of functionalizing graphene surfaces, deposited on electrodes, in order to prevent their oxidation while still allowing the ET and more generally molecules useful in molecular electronics. This was described in final Chapter.