Cavitand receptors for chiral recognition and fluorescent sensing

The need to develop sensors specific for different classes of analytes is well recognized and confirmed by the considerable research efforts spent for the preparation of more and more efficient devices. The crucial parameter to define the success of a given sensor is therefore selectivity, and for this reason the strategy to prepare the sensing material following the principle of supramolecular chemistry has quickly gained increasing importance. Within this context, the present thesis focused on the realization and characterization of supramolecular receptors as material for sensing chemicals vapors such as alcohols and nitroaromatics. In detail, we have conceived and prepared mixed bridged phosphonate cavitands and quinoxaline cavitands, probing their molecular recognition properties toward suitable guest at the gas solid interface and in solution. A new highly selective fluorescent sensor for C1-C4 alcohols has been prepared, in which only the specific interactions between the analyte and the sensing layer are transduced into a readable signals. Inherently chiral cavitands were also prepared, capable of enantiospecific recognition in the solid state toward chiral alcohols and in solution toward L-amino acids.