Biomedical Sciences

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Discrete Functionalization of Resorcinarenes for Applications in Supramolecular Chemistry
(2023-01-01) Twum, Kwaku; Beyeh, Ngong K.; Sevilla, Michael; Yang, Ziming; Madlambayan, Gerard
Resorcinarenes are three-dimensional cyclic oligomers obtained by acid-catalyzed condensation between resorcinol and an appropriate aldehyde. This doctoral thesis research presents basic and translational research studies that demonstrate the versatile functionalization and applications of the resorcinarene macrocycle. In chapter one, this thesis introduces macrocyclic chemistry with a brief reflection on the history of the science and Beyeh Lab’s use of the resorcinarene macrocycle in supramolecular chemistry. Chapter two presents a fundamental study of cooperativity in non-covalent interactions using a resorcinarene as an anchor to a guest in a solution that restricts its free rotation in the solution. Chapter three explores the molecular recognition potential of functionalized resorcinarenes as sensors for ammonium cations and pyrophosphate anions. Last, chapter four presents functionalized water-soluble resorcinarenes as aggregation inhibitors for peptides that cause eye cataracts. These applications are all realized through the persistent hydrophobic cavity inherent in the basic resorcinarene cavitand and the synthetic functionalization of the macrocyclic ring, which underscores the versatile use of resorcinarene compounds in supramolecular chemistry.