%0 Journal Article
%A Metzler, Maurice
%A Virovets, Alexandr
%A Lerner, Hans-Wolfram
%A Wagner, Matthias
%T B<sub>2</sub>,N<sub>4</sub> -Doped Heptacenes: Ambipolar Charge-Transfer Compounds with Deep LUMO Levels
%J Journal of the American Chemical Society
%V 145
%N 43
%@ 0002-7863
%C Washington, DC
%I ACS Publications
%M PUBDB-2023-06579
%P 23824 - 23831
%D 2023
%Z Waiting for fulltext 
%X The B<sub>2</sub>,N<sub>4</sub>-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<sub>2</sub>C<sub>4</sub> core.
%F PUB:(DE-HGF)16
%9 Journal Article
%$ 37862629
%U <Go to ISI:>//WOS:001095366600001
%R 10.1021/jacs.3c09029
%U https://bib-pubdb1.desy.de/record/597365