One-Pot Synthesis of Triazatriphenylene Using the Povarov Reaction

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  • Sachie Yamamoto
    Tsukuba Research Center for Energy Materials Science (TREMS), Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8573, Japan
  • Zong Yang Zhou
    Tsukuba Research Center for Energy Materials Science (TREMS), Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8573, Japan
  • Goki Hiruta
    Tsukuba Research Center for Energy Materials Science (TREMS), Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8573, Japan
  • Katsuhiko Takeuchi
    National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan
  • Jun-Chul Choi
    National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan
  • Takeshi Yasuda
    Research Center for Functional Materials, National Institute for Materials Science (NIMS), 1-2-1 Sengen, Tsukuba, Ibaraki 305-0047, Japan
  • Takaki Kanbara
    Tsukuba Research Center for Energy Materials Science (TREMS), Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8573, Japan
  • Junpei Kuwabara
    Tsukuba Research Center for Energy Materials Science (TREMS), Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8573, Japan

書誌事項

公開日
2021-05-26
権利情報
  • https://doi.org/10.15223/policy-029
  • https://doi.org/10.15223/policy-037
  • https://doi.org/10.15223/policy-045
DOI
  • 10.1021/acs.joc.1c00078
公開者
American Chemical Society (ACS)

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説明

The Povarov reaction combines aromatic amines, aldehydes, and alkynes in a single step and is regarded as an annulative π-extension reaction of aromatic amines. In this study, the Povarov reaction was investigated as an efficient tool for the synthesis of aza-polycyclic aromatic hydrocarbons via multiple π-extensions. The double Povarov reaction of 1,4-diaminobenzene yielded the 4,7-phenanthroline derivative as the major product, regardless of the steric repulsion in the product. The site selectivity mainly depended on the HOMO distribution of the intermediate rather than the steric factor. Based on these insights, a 1,5,9-triazatriphenylene derivative was synthesized via a triple Povarov reaction. The structures of the synthesized compounds were unambiguously determined by single-crystal X-ray diffraction analysis. The triazatriphenylene derivative formed a smooth and stable thin film upon vacuum vapor deposition and served as a hole-blocking material in organic light-emitting diodes.

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