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@ARTICLE{Metzler:597365,
      author       = {Metzler, Maurice and Virovets, Alexandr and Lerner,
                      Hans-Wolfram and Wagner, Matthias},
      title        = {{B}$_2$,{N}$_4$ -{D}oped {H}eptacenes: {A}mbipolar
                      {C}harge-{T}ransfer {C}ompounds with {D}eep {LUMO} {L}evels},
      journal      = {Journal of the American Chemical Society},
      volume       = {145},
      number       = {43},
      issn         = {0002-7863},
      address      = {Washington, DC},
      publisher    = {ACS Publications},
      reportid     = {PUBDB-2023-06579},
      pages        = {23824 - 23831},
      year         = {2023},
      note         = {Waiting for fulltext},
      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.},
      cin          = {DOOR ; HAS-User},
      ddc          = {540},
      cid          = {I:(DE-H253)HAS-User-20120731},
      pnm          = {6G3 - PETRA III (DESY) (POF4-6G3) / FS-Proposal: I-20220822
                      (I-20220822)},
      pid          = {G:(DE-HGF)POF4-6G3 / G:(DE-H253)I-20220822},
      experiment   = {EXP:(DE-H253)P-P24-20150101},
      typ          = {PUB:(DE-HGF)16},
      pubmed       = {37862629},
      UT           = {WOS:001095366600001},
      doi          = {10.1021/jacs.3c09029},
      url          = {https://bib-pubdb1.desy.de/record/597365},
}