In this thesis, different strategies for obtaining azaacenes suitable for solution-based
processing techniques have been investigated and developed.
The first synthetic approach involved the condensation of commercially available
compounds which include the diamines 2,3-diaminobenzene, 2,3-diaminonaphtalene
and 2,3-diaminophenazine and the bromoanilic acid and embelin. This synthetic route
yielded a series of dihydroazaacenes with 5 and 7 fused aromatic rings. The low
overall solubility of this azaacenes did not permit an extensive characterization of the
compounds.
A second synthetic approach was developed to investigate both C-N exchange and
lateral expansion of the π-conjugation. Through this approach a tetraazaoctacene
derivative was obtained and characterized. However it lacked of solubility necessary
for being compatible with solution-processing techniques.
A third strategy was based on the introduction of solubilizing groups on such
extended tetraazaoctacene core. While the di-substitution did not render the
azaoctacene soluble in neutral media, tetra-substitution yielded a derivative with
enhanced solubility in neutral solvent.
