Calixarene-based ion or ion-pair receptors
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Calixarene derivatives are one of the most important supramolecular scaffolds. They have been extensively exploited to build more elaborate systems. Calixarene derivatives can stabilize host-guest complexes with various ions and neutral molecular guests through non-covalent interactions (e.g., hydrogen bonding, electrostatic interactions and cation-π interactions). This dissertation describes efforts to develop more efficient calixarene-based ion and ion-pair receptors. Chapter 1 describes an overview of sensitive ion selective chromogenic and fluoregenic sensors based on calixarene derivatives. Chapter 2 details a chromogenic calixarene-calixpyrrole sensor system formed by appending an indane substituent to the β-pyrrole position of the calixpyrrole portion of the hybrid and its use in detecting cesium salts. The indane substituted calixarene-calixpyrrole system gives rise to a colorimetric response when only exposed to simple ion pairs containing the cesium cation. Chapter 3 describes amido-indole incorporated calixarene anion receptors. An amido-indole moieties appended calixarene provides multiple hydrogen bond donors for the interaction with anions. In Chapter 4, graphene field-effect transistors (GFETs) are introduced for cesium ion sensing based on electrostatic measurements. In this work, a crown-6-ether strapped calixarene derivative that adopts a cesium ion selective conformation was prepared. Then, it was attached to various graphene field-effect transistors (GFETs) via π−π interactions. The co-complexation of Cs⁺ ion and calixarene receptor on the GFETs alters the electronic behavior of the system in an ion and concentration dependent manner. This work serves to extend the fundamental chemistry of calixarene-based cesium ion recognition to new research areas. Lastly, an experimental section and characterization data are provided in Chapter 5.