We report the use of our recently-discovered sterically-driven hypervalent iodine oxyacid-mediated oxidation of 2,7-di-tert-butylpyrene in devising an efficient synthetic pathway for both asymmetric pyrene-fused pyrazaacenes (asymmetric PPAs or N-heteroacenes) and pyrene-fused pyrazinocyanines (PPycs). A series of asymmetric PPAs was synthesized in good yields using an oxidize-condense-oxidize-condense four-step sequence starting from 2,7-di-tert-butylpyrene. This sequence is an improvement over the sequential condensations between, e.g., 2,7-di-tert-butylpyrene-4,5,9,10-tetraone and different ortho-diamines in stoichiometrically-controlled conditions, which can severely limit the flexibility of the synthetic route and result in symmetric PPA byproducts, Moreover, the asymmetric PPAs with one phthalonitrile end were cyclized into the corresponding Pycs. We present the synthesis and photophysical properties of these new compounds.

Asymmetric pyrene-fused pyrazaacenes and pyrazinocyanines through the Green oxidation of 2,7-di-tert-butylpyrene

ACS Spring 2022

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