Intramolecular Borylation via Sequential B−Mes Bond Cleavage for the Divergent Synthesis of B,N,B-Doped Benzo[4]helicenes

Julius A. Knöller, Guoyun Meng, Xiang Wang, David Hall, Anton Pershin, David Beljonne, Yoann Olivier, Sabine Laschat, Eli Zysman-Colman, Suning Wang

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Abstract

New symmetric and unsymmetric B,N,B-doped benzo[4]helicenes 3–6 a/b have been achieved in good yields, using a three-step process, starting from N(tolyl)3 in a highly divergent manner (7 examples). A borinic acid functionalized 1,4-B,N-anthracene 1 was found to display unprecedented reactivity, acting as a convenient and highly effective precursor for selective formation of bromo-substituted B,N,B-benzo[4]helicenes 2 a/2 b via intramolecular borylation and sequential B−Mes bond cleavage in the presence of BBr3. Subsequent reaction of 2 a/2 b with Ar-Li provided a highly effective toolbox for the preparation of symmetrically/unsymmetrically functionalized B,N,B-helicenes. Their high photoluminescence quantum yields along with the small ΔEST suggest their potential as thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs).

Original languageEnglish
Pages (from-to)3156-3160
Number of pages5
JournalAngewandte Chemie - International Edition
Volume59
Issue number8
DOIs
Publication statusPublished - 17 Feb 2020

Keywords

  • B,N,B-benzo[4]helicenes
  • boron
  • divergent synthesis
  • luminescence
  • synthetic methods

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  • Datasets

    CCDC 1946485: Experimental Crystal Structure Determination

    Knöller, J. A. (Creator), Meng, G. (Creator), Wang, X. (Creator), Hall, D. (Creator), Pershin, A. (Creator), Beljonne, D. (Creator), Olivier, Y. (Contributor), Laschat, S. (Creator), Zysman‐Colman, E. (Creator) & Wang, S. (Creator), University of Namur, 17 Feb 2020

    Dataset

    CCDC 1946488: Experimental Crystal Structure Determination

    Knöller, J. A. (Creator), Meng, G. (Creator), Wang, X. (Creator), Hall, D. (Creator), Pershin, A. (Creator), Beljonne, D. (Creator), Olivier, Y. (Contributor), Laschat, S. (Creator), Zysman‐Colman, E. (Creator) & Wang, S. (Creator), University of Namur, 17 Feb 2020

    Dataset

    CCDC 1946489: Experimental Crystal Structure Determination

    Knöller, J. A. (Creator), Meng, G. (Creator), Wang, X. (Creator), Hall, D. (Creator), Pershin, A. (Creator), Beljonne, D. (Creator), Olivier, Y. (Contributor), Laschat, S. (Creator), Zysman‐Colman, E. (Creator) & Wang, S. (Creator), University of Namur, 17 Feb 2020

    Dataset

    Cite this

    Knöller, J. A., Meng, G., Wang, X., Hall, D., Pershin, A., Beljonne, D., Olivier, Y., Laschat, S., Zysman-Colman, E., & Wang, S. (2020). Intramolecular Borylation via Sequential B−Mes Bond Cleavage for the Divergent Synthesis of B,N,B-Doped Benzo[4]helicenes. Angewandte Chemie - International Edition, 59(8), 3156-3160. https://doi.org/10.1002/anie.201912340