Azahelicene‐Fused BODIPY Analogues Showing Circularly Polarized Luminescence

Helical carbazole‐based BODIPY analogues were readily synthesized via aza[7]helicenes. The structures of azahelicene‐incorporated BF2 dyes were elucidated by x‐ray diffraction analysis. DFT calculations revealed that the π‐conjugated system expanded from the helicene moiety to the BODIPY framework....

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Bibliographic Details
Published inAngewandte Chemie Vol. 132; no. 20; pp. 7887 - 7891
Main Authors Maeda, Chihiro, Nagahata, Keiji, Shirakawa, Takuma, Ema, Tadashi
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 11.05.2020
Subjects
BODIPY
Boron
Carbazole
Carbazoles
Chemistry
Circular polarization
Dyes
Farbstoffe
Helicene
Luminescence
Zirkular polarisierte Lumineszenz
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Summary:Helical carbazole‐based BODIPY analogues were readily synthesized via aza[7]helicenes. The structures of azahelicene‐incorporated BF2 dyes were elucidated by x‐ray diffraction analysis. DFT calculations revealed that the π‐conjugated system expanded from the helicene moiety to the BODIPY framework. The azahelicene‐fused boron complexes showed the Cotton effects and the circularly polarized luminescence (CPL) in the visible region. Furthermore, an axially chiral binaphthyl group was attached to the helically chiral dyes, which enhanced the chiroptical properties. Eine polarisierende Wendung: Helikale Borkomplexe auf Carbazol‐Basis wurden leicht über Aza[7]helicene synthetisiert. Das π‐konjugierte System expandierte von der Helicen‐Einheit zum BODIPY‐Gerüst, und die azahelicenkondensierten Borkomplexe zeigten die Cotton‐Effekte und eine deutlich zirkular polarisierte Lumineszenz (CPL) im sichtbaren Bereich.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202001186