Synthese en bindingseigenschappen van aza- en thiapillararenen: op weg naar nieuwe heteramacrocyclische verbindingen binnen de pillarareenfamilie

Since their discovery in 2008, pillararenes have gained a vast amount of attention within the field of supramolecular chemistry. These macrocycles have various beneficial properties such as short and inexpensive synthetic routes, rigid frameworks, tunable solubilities, and easy functionalizations. As the synthesis of larger ring size pillararenes is often accompanied by lower yields, they have not been extensively studied yet. However, hosts with larger cavities remain of interest as they could enable complexation to a variety of novel guests. One way to achieve this structural feature is by using heteramacrocylic dithiapillararenes, which have already been obtained in high yields. Unfortunately, the low chemical stability of the disulfides hampers their widespread implementation. To combine larger cavities and a good chemical stability, this project focusses on the synthesis of a novel class of heterapillararenes, called thiapillararenes. Their soft sulfur atoms and the possibility to oxidize them can potentially lead to a novel class of chiral hosts with tunable host-guest properties. This in turn could enable selective recognition of chiral guests. As such, the project has two goals in mind. Firstly, synthetic routes towards thiapillararenes with different ring sizes and sulfur content will be developed. Secondly, the obtained molecules will be functionalized, and their binding properties will be evaluated.