H-Bonding in supramolecular sensing and ion-channels self-assembly

In this thesis we have investigated the crucial role of H-bonding interactions in supramolecular sensing and ion-channels formation. In the first case, we have demonstrated how the presence of a preorganized receptor, which bears specific functionalities, is essential for an effective molecular recognition process. In detail, we have conceived tetraphosphonate and mixed bridged thio-phosphonate cavitands, and probed their molecular recognition properties toward alcohols at the gas solid interface by using QCM sensor devices. On one hand, these receptors have shown a very high sensibility toward all alcohols and on the other, a good selectivity for short chain alcohols. In the second part of the thesis, we have directed the attention on different supramolecular structures able to self-assemble in ion-channel. We have conceived a ditopic guanosine-sterol derivative and we have tested its aggregation ability by using planar lipid bilayer experiments. Finally, we have demonstrated how the combination of the hydrophobic and hydrophilic aspects of this compound, affords the self-assembly of large and stable transmembrane ion-channels