4.8 Article

Divergent Synthesis of Heteroatom-Centered 4,8,12-Triazatriangulenes

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 18, Pages 5087-5090

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201701246

Keywords

divergent synthesis; electrophilic substitution; heterocycles; triangulenes; X-ray diffraction

Funding

  1. Ministry of Education, Culture, Sports, Science & Technology in Japan (MEXT) [15H01004, 26288095]
  2. Accelerated Innovation Research Initiative Turning Top Science and Ideas into High-Impact Values (ACCEL) program of JST
  3. Mitsubishi Foundation
  4. Grants-in-Aid for Scientific Research [26288095, 16J02975, 15H01004] Funding Source: KAKEN

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The increasing attention devoted to triangulenes and their heteroatom derivatives inspired us to explore a divergent synthesis of heteroatom-centered 4,8,12-triazatriangulenes, which involved the preparation of a nitrogen-containing macrocyclic precursor and subsequent central heteroatom introduction by electrophilic C-Li and C-H substitution. The boron-centered triangulene has a planar structure unlike the bowl-shaped phosphorus-and silicon-centered triangulenes. The described synthetic procedure can be used to fabricate a broad range of attractive functional materials, for example, for organic light-emitting diodes, based on heteroatom-centered triangulenes.

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