Synthesis of Emissive Heteroacene Derivatives via Nucleophilic Aromatic Substitution

A synthetic
approach for preparing a variety of heterocyclic tetrahydropentacene
derivatives via nucleophilic aromatic substitution reactions of bidentate
nucleophiles and tetrafluorotere­phthalonitrile was developed.
X-ray crystallography of several products revealed that the compounds
containing oxygen and nitrogen heteroatoms are highly planar and engage
in π-stacking, while the compounds containing sulfur are bent
and do not stack as effectively. The compounds were also highly emissive,
and the heteroatom had a significant impact on the emission and electrochemical
properties.