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Novel cyclohexane-based receptors for anion binding and transport

This thesis describes a series of novel anionophores and details their synthesis, anion binding and anion transport capabilities. These novel anionophores are based on a cyclohexane scaffold CA, Figure 1), and are simpler to synthesise than the cholapod and decal ins CB and C in Figure 1 respectively) previously reported by the Davis group. Association constants for chloride were evaluated for the new cyclohexane-based receptors in DMSO-d6/0.S% H20 and, where solubility permitted, in water-saturated chloroform. For the novel cyclohexane systems A, higher association constants were obtained where R = Me as opposed to R = H as well as for those receptors possessing electron-deficient aromatics. However the association constants of these novel systems were found to be somewhat lower than those seen previously with cholapods and decalins. Anion transport by these new cyclohexanes was evaluated by the lucigenin method, with the majority of receptors displaying measurable anion transport activity. As with anion binding, higher levels of transport were obtained where R = Me as opposed to R = H and where aromatics were electron-deficient. Certain cyclohexane-based receptors were found to have similar or improved rates of transport when compared to previously reported receptors from the Davis group, including one which is the most active anion transporter reported by the Davis group. Some progress has also been made towards altering the identity of the hydrogen bond donors on the scaffold, further modifying appended alkyl units and a novel squaramide macrocycle.

Identiferoai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:683940
Date January 2016
CreatorsCooper, James Arthur
PublisherUniversity of Bristol
Source SetsEthos UK
Detected LanguageEnglish
TypeElectronic Thesis or Dissertation

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