The overarching aim of the present project is the synthesis and the study of the applications of molecular containers/receptors that possess polar interiors derived from the use of aryl-extended calix[4]pyrrole units. First, we propose the synthesis of containers / receptors with covalent structure (cavitands), as well as self-assembled analogs through the use of covalent reversible bonds (e.g. coordination bonds or dynamic covalent bonds) or mechanical bonds (i.e. rotaxanes). The prepared receptors will have a cavity large enough to include or encapsulate neutral or charged polar molecules of low molecular weight, which are of some relevance to health and/or the environment. We want to synthesize containers / receptors that are soluble in organic solutions and subsequently evolve them towards related compounds but soluble in aqueous solutions. Water is the natural medium of many of the analytes that we intend to recognize and detect.
Second, we will study the binding processes of the synthesized receptors / co-presenters against different analytes, both in organic solvents and in water. These processes will be thermodynamically and kinetically characterized in detail. With this methodology we hope to advance in our knowledge about their binding properties and to be able to design modified versions with improved properties. Finally, the applications that we intend to address include their conversion into molecular sensors (i.e. fluorescent receptors or receptors immobilized on the surface of nanoparticles), their use as molecular carriers for the transport of neutral and charged molecular cargo through lipid
membranes (i.e. mainly transport of anions and amino acids), as well as the study of the chemical reactivity and intermolecular interactions of molecules confined in their inner cavities.