This thesis describes the development and synthesis of a range of novel fluorophores based on 1,8-naphthalimide, N-heterocyclic carbene (NHC) and phosphine derivatives, as well as coordination chemistry with Au(I), Ir(III) and Fe(II). Detailed discussions on the characterisation and the photophysical properties are described, with reference to applications including bioimaging, diagnostics and therapeutics. Chapter 2 describes the synthetic development and spectroscopic analysis of a series of NHC-functionalised 1,8-naphthalimide fluorophores, generating ten new ligands that were successfully utilised for Au(I) coordination chemistry. The optical properties of the compounds were dictated by ligand-centred transitions. Cytotoxicity assessments revealed that compounds were the most toxic to LOVO and MCF-7 cell lines. In addition, lysosomal localisation was observed in cell imaging studies with MCF-7 cells, as seen with structurally related anticancer compounds. Chapter 3 describes the synthetic development and spectroscopic analysis of a series of aminophosphine and phosphinite fluorophores, generating six new ligands, with some successfully utilised for Au(I) coordination chemistry. The photophysical properties were explored in detail due to the presence of different fluorescent groups, including naphthalene, anthracene, pyrene and anthraquinone. In this chapter, 31P NMR was particularly important in confirming the success of the synthetic routes. Chapter 4 describes the comparative syntheses of six new phenyl-1H-pyrazoles and their corresponding cyclometalated iridium(III) complexes using both batch and, successfully applied, flow-microwave methodologies. Isolation of spectroscopically pure species in less than 1 hour of reaction time from IrCl3 was observed, along with ligand-dependent, tuneable green-yellow luminescence. Chapter 5 outlines determination of a successful synthetic route to a series of fluorescent electrochemical biosensors that incorporate both a redox active ferrocene unit and a naphthalimide moiety, with the intention to be applied as an electrochemical detection method for Clostridium Difficile (CDF). Detailed photophysical and electrochemical investigations were used to determine suitability for the desired application.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:732300 |
| Date | January 2017 |
| Creators | Groves, Lara |
| Publisher | Cardiff University |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://orca.cf.ac.uk/108908/ |
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