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| Home > Publications database > B$_2$,N$_4$ -Doped Heptacenes: Ambipolar Charge-Transfer Compounds with Deep LUMO Levels |
| Home > Publications database > B$_2$,N$_4$ -Doped Heptacenes: Ambipolar Charge-Transfer Compounds with Deep LUMO Levels |
| Journal Article | PUBDB-2023-06579 |
; ; ;
2023
ACS Publications
Washington, DC
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Please use a persistent id in citations: doi:10.1021/jacs.3c09029
Abstract: The B$_2$,N$_4$-doped heptacene H4 in which two N,N′-dihydrophenazine units are linked by two BMes bridges (Mes = mesityl) was synthesized via fourfold Buchwald−Hartwig coupling between 2,3,6,7-tetrachloro-9,10-dimesityl-9,10-dihydro-9,10-diboraanthracene and o-phenylenediamine (tBuXPhos-Pd-G3, DBU/NaOTf, 2-MeTHF, 50 °C, 16 h). Upon exposure to ambient air, H4 is oxidized to its N,N′-dihydro form H2; further oxidation with MnO2 furnishes the di(phenazine) derivative H0. Stirring under a blanket of H2 in the presence of Pd/C hydrogenates H0 back to H2 and ultimately H4. Yellow-colored H0 is a remarkably good electron acceptor with a LUMO-energy level of −3.9 eV; upon irradiation with a 405 nm LED in the presence of THF or 1,4-cyclohexadiene, H0 accepts two H atoms to furnish H2. One-electron reduction of H0 yields the isolable radical-anion salt Li[H0] (lithium naphthalenide, THF, −30 °C to rt). The ambipolar compounds H2 and H4 possess a navy blue and deep purple color, respectively, due to charge-transfer interactions from the electron-rich N,N′-dihydrophenazine donor(s) to the electron-accepting B$_2$C$_4$ core.
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