Date of Award
Master of Science (MS)
1,6,7,12-tetrachloroperylene tetracarboxylic acid anhydride (PDACl4) is a fluorescent dye with a wide range of tunability. This work explores the functionalization of PDACl4 to exploit its supramolecular and photovoltaic (PV) capabilities. Synthesis of a novel pillared paddlewheel (PPW) metal-organic framework (MOF) using a bipyridyl functionalized tetrachloro perylene diimide (BPyPDICl4) pillar with 2,6-naphthalenedicarboxylic acid (2,6-NDC) struts was successfully achieved and confirmed with X-ray diffraction (XRD). The growth of the new MOF as a thin film on both zinc oxide and titanium dioxide-coated fluorine-doped tin oxide (FTO) glass was explored for its potential use in dye-sensitized solar cell (DSSC) type application using powder x-ray diffraction (PXRD), UV-Vis, and diffuse reflectance (DR) spectroscopy. Other solvothermal syntheses of UiO, MOF-5, and PPF-type MOFs using tetrachloro perylene diimide (PDICl4) ligands were performed and discussed. Organic synthesis of a new 4-tert-butylaniline based tetrachloro perylene diimide is reported along with its potential as a reaction intermediate. Bay substitution with cyclohexylamine, pyrrolidine, 1,2-dimethylhydrazie, 2-methoxyethanol, and pentaethylene glycol on various PDICl4 derivatives is investigated through different synthetic routes with a final goal of substituting all four bay position with electron-rich or cation-coordinating moieties on a perylene diimide with metal-coordinating imide groups. Future direction for the novel MOF and the application of the newly synthesized PDI ligands in MOF application is discussed.
Palukoshka, Andrei, "Functionalization of 1,6,7,12-Tetrachloroperylene Tetracarboxylic Acid Anhydride for Synthesis of Metal-Organic Frameworks in Energy Applications" (2020). All Theses. 3311.