Mirri, Giorgio (2011)
Ph.D. thesis, University of Birmingham.
Chiral recognition, determination of enantiomeric excess and the separation of enantiomers are challenging problems for the chemist. This work has as its aim the design and syntheses of new electrochemical chiral receptors for neutral molecules. All the receptors prepared contain a ferrocene group as electroactive reporting unit. The differences among the receptors mainly relate to the binding site and the chiral group. The first type of receptor, presented in Chapter 2, consists of chiral ferrocene containing boronic acids that have been used to electrochemically sense aromatic and aliphatic chiral and achiral diols. The electrochemical determination of the enantiomeric excess of a mixture of two enantiomers of Binol performed with one of these boronic acids represents a new advance in supramolecular chiral sensing. In Chapter 3 the synthesis of ferrocene-containing chiral macrocycles of different sizes is described. The binding site is a cavity featuring a diamidopyridine moiety, with the chirality introduced through a Binol unit. These receptors showed low interaction with achiral cyclic ureas and chiral carboxylic acids. Chapter 4 describes the study of self-assembled monolayers onto gold surfaces. The monolayers are formed by ferrocene-containing amides of lipoic (thioctic) acid and, for the first time, isolipoic acid. The studies indicate that isolipoic acid could be an attractive anchor group for SAM formation when strong control over the chirality of the monolayer is required.
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