Synthesis of 1, 13‐Dichloro 5, 6, 8, 9‐Tetraaza Dibenzo Anthracene, Helical Considerations

Helix‐shaped aromatic molecules or helicenes play an important role as building blocks of helical conjugated polymers and other compounds with unique material properties. Since helicenes are chiral conjugated molecules, they are useful as chiral derivatizing agents and as enantioselective complexing agents. They are also useful as chiral auxiliaries, as inducers of enantioselectivity, and as fluorescence sensors. Both [N]helicenes and helical [N]phenylenes are structures that exhibit unusual chiro‐optical, electro‐optical and fluorescence properties which constitute the cornerstone in many modern devices, from optic fibers to liquid‐crystal displays (LCD) and light‐emitting diodes (LED). These modern devices are found in most medical sensors such as biomedical spectroscopic sensors. Additionally, helical [N]phenylenes can serve as catalysts for enantioselective transformations, owing to their chirality. Given that the liquid crystal phase requires that the molecule be rigid in its central position and flexible at the extremities, a novel helix‐shaped molecule was designed using diazaanthracene as the central core. Therefore, it is hypothesized that the title compound fitting such parameters, 1,13‐dichloro 5,6,8,9‐tetraaza dibenzo anthracene could be prepared from 2,3 dichloronitro benzene and 1,5‐dinitro 2,4‐dichloro benzene by a two step synthesis, nitration and Ullmann coupling. Advantage was taken of the fact that a facile ring‐forming diazotization reaction was to follow a straight forward novel Ullmann coupling triarylation. Using these steps, a helicene‐like compound 1,13‐dichloro 5,6,8,9‐tetraaza dibenzo anthracene was synthesized. Nuclear Magnetic Resonance (NMR) of the compound synthesized has shown the presence of the titled compound and is undergoing further characterizations such as Gas Chromatography‐Mass Spectrometry (GC‐MS) and single crystal x‐ray. Supported by NIH 2T34GM008411