Intramolecular borylation via sequential B-Mes bond cleavage for the divergent synthesis of B,N,B-doped benzo[4]helicenes

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

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)
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Abstract

New symmetric and unsymmetric B,N,B-doped benzo[4]helicenes 3 - 6a/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 2a/2b via intramolecular borylation and sequential B-Mes bond cleavage in presence of BBr3. Subsequent reaction of 2a/2b 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 ∆EST suggest the potential as thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs).
Original languageEnglish
JournalAngewandte Chemie International Edition
VolumeEarly View
Early online date16 Jan 2020
DOIs
Publication statusE-pub ahead of print - 16 Jan 2020

Keywords

  • Synthetic methods
  • Boron
  • Luminescence
  • B,N,B- benzo[4]helicenes
  • Divergent synthesis

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