Syntheses of calix[4]pyrrole–based receptors and applications for therapeutics and environmental remediation

Significant efforts have been made to develop synthetic receptors with high selectivity and affinity for specific anions or ion pairs. Calix[4]pyrroles, conformationally flexible tetrapyrrolic macrocycles defined by sp³ hybridized meso bridges, have emerged as one of the essential supramolecular hosts for anion and ion pair recognition. This dissertation describes efforts to develop functional calix[4]pyrroles that might allow their eventual use as therapeutics and in environmental remediation applications. A series of calix[4]pyrroles were prepared by functionalizing the parent calix[4]pyrrole at the so–called meso bridges, including mono–walled calix[4]pyrroles, double–walled calix[4]pyrroles, and strapped calix[4]pyrroles. Chapter 1 provides a brief overview of calix[4]pyrroles, calix[4]pyrrole–based anion transporters, and hydroxide extraction based on host–guest chemistry. Chapter 2 summarizes synthetic developments focused on preparing new calix[4]pyrroles. Chapter 3 details studies devoted to establishing correlations between changes in intracellular cation concentrations and cancer cell death. Chapter 4 describes the recognition and extraction of sodium hydroxide using calix[4]pyrrole–based ion pair receptors. Chapter 5 provides the synthetic procedures and the characterization data for all new compounds used in these studies.Chemistr