Ultra-electron-deficient azaacenes were synthesized via Buchwald-Hartwig coupling of ortho-diaminoarenes with chlorinated mellophanic diimide followed by oxidation of the intermediate N,N'-dihydro compounds with MnO or PbO . The resulting cata-annulated bisimide azaacenes have ultrahigh electron affinities with first reduction potentials as low as -0.35 V recorded for a tetraazapentacene. Attempts to prepare a tetrakis(dicarboximide)tetraazaheptacene resulted in the formation of a symmetric butterfly dimer.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8457205 | PMC |
| http://dx.doi.org/10.1002/chem.202101573 | DOI Listing |
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