ACYCLIC CUCURBIT[N]URIL MOLECULAR RECEPTORS: SEQUESTRANTS FOR DRUGS, MICROPOLLUTANTS, AND IODINE

Abstract

Molecular containers are extensively utilized for their exceptional molecular recognition capabilities, making them suitable for use as sensors and sequestration agents. Cucurbit[n]urils, in particular, are recognized for their strong binding affinities, especially towards cationic guest molecules. These applications can be further enhanced by adjusting the size and shape of the host and incorporating functional groups.In Chapter 1, the concept of supramolecular chemistry is introduced, with a specific focus on cucurbit[n]urils. The chapter provides an overview of the development of cucurbit[n]urils and their potential applications. It also addresses the challenge of poor water solubility of cucurbit[n]urils, and discusses the enhancement of water solubility through the development of acyclic CB[n]s. Furthermore, the potential application of these containers as sequestration agents is explored. Chapter 2 describes the synthesis of a novel sulfated acyclic CB[n] receptor (Me4TetM0) and its recognition properties towards a panel of drugs of abuse. The obtained results were compared with two other sulfated acyclic CB[n]s (TetM0 and TriM0). Furthermore, in vivo studies were conducted with TetM0 to assess its efficacy as a sequestration agent for methamphetamine. Chapter 3 presents the synthesis of a series of water insoluble acyclic CB[n]-type receptors and studies their function as solid state sequestrants for organic micropollutants. The results are compared with CB[6] and CB[8]. The time course experiments performed with H4 show a rapid sequestration ability of the five micropollutants studied. Furthermore, under identical conditions, the micropollutant removal efficiency is higher than activated charcoal. Chapter 4 investigates the use of water-insoluble acyclic CB[n]-type receptors for the reversible capture of iodine from the vapor phase. H2 exhibits an iodine capture of 2.2 g g-1, equivalent to 12 iodine atoms per H2 molecule. Following iodine uptake, H2 undergoes partial oxidation, and the uptake of I3- and I5- was confirmed through Raman spectroscopy. Chapter 5 details the synthesis of glycoluril dimer bis(cyclic) ether-based hosts with diverse aromatic side walls. The chapter presents a comparative analysis of dye removal from a solid state and delves into the influence of distinct aromatic walls and various attached substituents.