Electron Acceptors and Donors Based on Heteroatom-doped Polycyclic Aromatic Scaffolds

Within the scope of this doctoral thesis, the chemistry of 6,13-dihydro-6,13-diazapentacene was investigated. Methodologies for the N-arylation were explored and a series of differently substituted N,N’-diarylated 6,13-dihydro-6,13-diazapentacenes were synthesized. Moreover, derivatizations at the positions adjacent to the nitrogen atoms were performed. Selected derivatives were subjected to various cyclization reactions to yield novel azaacene-based π expanded polycyclic aromatic hydrocarbons. The fundamental characteristics of the obtained cyclized products were compared to the corresponding non-cyclized compounds. The obtained derivatives were characterized by NMR and IR spectroscopy as well as mass spectrometry. Furthermore, the derivatives were investigated regarding their photophysical and electrochemical properties in solution (UV/vis spectroscopy, cyclic voltammetry) as well as their structural characteristics in the solid state (X-ray crystallographic analysis). The experimental data were corroborated by theoretical calculations