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Synthesis of electrochromic oxygen-doped polycyclic aromatic hydrocarbons

Fletcher-Charles, Jack 2019. Synthesis of electrochromic oxygen-doped polycyclic aromatic hydrocarbons. MPhil Thesis, Cardiff University.
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Abstract

The synthesis of two O-doped anthracene-based molecules possessing red/pink colour was achieved. These molecules were found to possess high sensitivity to air and, according to literature, react with singlet oxygen.96 In addition, an air-stable O-doped naphthalene-based molecule, 3,10-di-tertbutylbenzo[ 3,4]isochromeno[7,8,1-mna]xanthene, was synthesised using a CuO mediated cyclisation reaction. A short investigation into the selectivity of the reaction using a reference molecule was carried out. This demonstrated that both pyrano and furano product formation was equally favoured. Attempts to synthesise a second naphthalene-based molecule, 2,6,9,13-tetra-tert-butylxantheno[2,1,9-mna]xanthene, led to the isolation of a difurano- molecule in 17 % yield and trace amounts of pyrano-furano- molecule. The spectroelectrochemical analysis of 3,10-di-tert-butylbenzo[3,4]isochromeno[7,8,1-mna]xanthene was performed, demonstrating a reversible colour change from yellow to blue at a potential of 0.9 V in solution. A drop-cast prototype ECD using and FTO-glass was constructed and gave rise to a device which exhibited the colour change described above at a potential of 2.0 V.

Item Type: Thesis (MPhil)
Date Type: Completion
Status: Unpublished
Schools: Chemistry
Funders: European Commission
Last Modified: 05 Nov 2019 10:22
URI: http://orca.cf.ac.uk/id/eprint/126562

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