Synthesis of a novel pendant side-chain conjugated perylene based polymer

Student thesis: Master thesis (including HD thesis)

  • Nils Johannes Klitmøller
4. Term, Chemistry, Master (polyt) (Master Programme)
The focus in this master thesis was developing a synthetic strategy for a novel perylene based monomer, capable of radical polymerization, resulting in side-chain conjugated homopolymers with possible photovoltaic properties, by p-p stacking of conjugated pendants. The monomer was synthesized through a 3-step process, followed by the fourth step, i.e., polymerization. Verification of the structure was done by 1H NMR and ATR FT-IR spectroscopy, and characterization of the polymer and intermediates included solubility analysis, UV/VIS absorbance and fluorescence spectroscopy and simultaneous thermogravimetric analysis. The synthesis was successful, resulting in a completely insoluble bright orange homopolymer. The low solubility of the intermediates led to the additional synthesis of perylene diimides with four different alkylamine substitutions, the most soluble of which was the diimide of sec-butylamine. Further synthesis of the diimides towards a similar homopolymer was however unsuccessful, due to the severely reduced reactivity in the Diels-Alder cycloaddition of maleic anhydride, in step two.
Publication date2 Oct 2015
Number of pages56
ID: 219674584