Chiral sensing is a challenging field for the chemist. Not many sensors for chiral recognition have been studied, and only a few examples of electrochemical chiral sensors are known in the literature. The aim of this project was to synthesise novel ferrocenyl-based chiral receptors, and to study their applications for chiral sensing in solution or upon incorporation onto gold surfaces as self-assembled monolayers (SAMs). From the solution studies it was possible to gain further information on the electrochemical behaviour of ferrocenyl-based receptors during the sensing of chiral carboxylates. The incorporation of receptors onto electrode surfaces led to an economy on the amount of compound required and higher sensitivity in analyte detection. However, the chiral recognition properties and the stability of the SAMs still need to be improved. Multifunctional receptors containing BINOL and ferrocenyl reporting groups were investigated to compare the use of electrochemistry and fluorescence spectroscopy in the chiral recognition of carboxylic acids, amino acid derivatives, or amino acid anions. Finally, a DNA analogue in which ferrocenyl units were incorporated in the backbone was studied. The electrochemical properties of this system as a single strand and in its interaction with complementary strands of DNA and PNA were investigated.
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