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Twofold C-H Activation Enables Synthesis of a Diazacoronene-type Fluorophore with Near Infrared Emission through Isosteric Replacement.

Authors
  • Greßies, Steffen1
  • Ito, Masato2
  • Sakai, Mika3
  • Osaki, Hiroshi2
  • Kim, Ju Hyun1
  • Gensch, Tobias1
  • Daniliuc, Constantin1
  • Ando, Naoki2
  • Yamaguchi, Shigehiro4
  • Glorius, Frank5
  • 1 Westfälische Wilhelms-Universität Münster: Westfalische Wilhelms-Universitat Munster, Chemistry, GERMANY. , (Germany)
  • 2 Nagoya University, Graduate School of Science, JAPAN. , (Japan)
  • 3 Nagoya University: Nagoya Daigaku, Graduate School of Science, JAPAN. , (Japan)
  • 4 Nagoya University: Nagoya Daigaku, Institute of Transformative Biomolecules, JAPAN. , (Japan)
  • 5 WWU Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149, Münster, GERMANY. , (Germany)
Type
Published Article
Journal
Chemistry - A European Journal
Publisher
Wiley (John Wiley & Sons)
Publication Date
Oct 21, 2020
Identifiers
DOI: 10.1002/chem.202004080
PMID: 33085826
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

The synthesis and photophysical properties of a soluble amide-embedded coronene is reported. The key step in this synthesis is the twofold C-H activation of diazaperylene by a rhodium(III)Cp* catalyst. This unprecedented structural motif shows intense fluorescence in the near infrared region with a small Stokes shift and a distinct vibronic structure, which exhibits a slight extent of negative solvatochromism. Comparison of this compound with some relevant compounds revealed the importance of the amide incorporation in the peripheral concave region including an angular position to retain high aromaticity reflecting that of parent coronene. Treatment of this compound with Lewis acid B(C6F5)3 formed a bis-adduct, which exhibited enhanced aromaticity as a consequence of the increased double bond character of the amide C-N bonds. © 2020 Wiley-VCH GmbH.

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