Isoamethyrin analogues and cyclo[n]pyrrole as sensors for cations and anions



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The increased worldwide interest in nuclear power and the politically charged threat of nuclear weapons release has made understanding the components, as well as the waste, of nuclear energy an important area of research. More specifically, the identification and selective extraction of the dioxoactinide cations uranyl (UO₂²⁺) and plutonyl (PuO₂⁺), low valent actinides scuh as Am³⁺ or Cm³⁺ and various anions, such as pertechnetate (TcO₄⁻), is essential in the event of a weapons release or the spill of nuclear waste. It has been previously demonstrated that the expanded porphyrin [24]hexaphyrin(, commonly referred to as isoamethyrin, displays a dramatic color change, from golden yellow to red, upon coordination of uranyl, neptunyl and plutonyl cations. Chapter 2 details quantitative investigations of isoamethyrin with the uranyl cation as well as the interactions of isoamethyrin with other, potentially competing, cations. This work was carried out in order to assess the ability of isoamethyrin to serve as a colorimetric sensor for the actinide cations. Chapter 3 describes the synthesis and properties of periphery-modified isoamethyrin analogues. The addition of functional groups to this expanded porphyrin allows for immobilization onto a solid support and may enhance its utility as a sensor. Chapter 4 presents the preliminary investigations into the metalation and anion binding properties of a new series of macrocycles, the cyclo[n]pyrroles. Chapter 5 provides experimental methods and characterization data.