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