Investigation of the Anion Binding Properties of Tripodal and Arylethynyl-Based Receptors
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Anion sensing is important due to the roles anions play in biological systems and the environment. Given the complexity of these environments, selectivity in receptors is crucial. Research in the labs of Profs. Darren Johnson and Mike Haley focuses on developing novel receptors which use non-covalent interactions to reversibly bind anions—ideally for use in sensors. This dissertation presents novel tripodal-structured receptors, as well as systems based on a previously established arylethynyl scaffold —a conjugated backbone that often provides fluorescent properties to the receptor. Chapter I is an introduction of the less commonly utilized non-colvalent interactions for anion binding—anion–π interactions and Caryl–H hydrogen bonds. The design and synthesis of cryptand and tripodal receptors with electron-deficient arenes ideal for anion–π interactions is presented in Chapter II. Chapters III and IV discuss work on novel tripodal 1,3,5-tris(arylethynyl)benzene receptors which demonstrate either anion–π interactions and Caryl–H···X– hydrogen bonds. A chloride selective bis(urea) arylethynylpyridine receptor is presented in Chapter V. Lastly, Chapter VI introduces initial efforts on the synthesis of mono(urea) arylethynyl receptors which will be used to further explore the anion–π binding capabilities of these systems and may also demonstrate the preference of anion–π binding interactions over Caryl–H hydrogen bonding when binding nitrate, as is demonstrated in Chapters III and IV. This dissertation includes previously published and unpublished coauthored material.