Azahelicene-Fused BODIPY Analogues Showing Circularly Polarized Luminescence

Chihiro Maeda; Keiji Nagahata; Takuma Shirakawa; Tadashi Ema

doi:10.1002/anie.202001186

Azahelicene-Fused BODIPY Analogues Showing Circularly Polarized Luminescence

Chihiro Maeda, Keiji Nagahata, Takuma Shirakawa, Tadashi Ema

Research output: Contribution to journal › Article › peer-review

61 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	7813-7817
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	59
Issue number	20
DOIs	https://doi.org/10.1002/anie.202001186
Publication status	Published - May 11 2020

Keywords

BODIPY
carbazoles
circularly polarized luminescence
dyes
helicenes

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.202001186

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title = "Azahelicene-Fused BODIPY Analogues Showing Circularly Polarized Luminescence",

abstract = "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.",

keywords = "BODIPY, carbazoles, circularly polarized luminescence, dyes, helicenes",

author = "Chihiro Maeda and Keiji Nagahata and Takuma Shirakawa and Tadashi Ema",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Number 18K05083, Tokuyama Science Foundation, and Wesco Scientific Promotion Foundation. We thank Prof. A. Osuka and Dr. T. Tanaka (Kyoto University) for x-ray diffraction analysis, fluorescence measurements and optical resolution, and Prof. H. Yorimitsu (Kyoto University) for mass measurements. Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2020",

month = may,

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doi = "10.1002/anie.202001186",

language = "English",

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AU - Maeda, Chihiro

AU - Nagahata, Keiji

AU - Shirakawa, Takuma

AU - Ema, Tadashi

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Number 18K05083, Tokuyama Science Foundation, and Wesco Scientific Promotion Foundation. We thank Prof. A. Osuka and Dr. T. Tanaka (Kyoto University) for x-ray diffraction analysis, fluorescence measurements and optical resolution, and Prof. H. Yorimitsu (Kyoto University) for mass measurements. Publisher Copyright: © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2020/5/11

Y1 - 2020/5/11

N2 - 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.

AB - 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.

KW - BODIPY

KW - carbazoles

KW - circularly polarized luminescence

KW - dyes

KW - helicenes

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JO - Angewandte Chemie - International Edition

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ER -

Azahelicene-Fused BODIPY Analogues Showing Circularly Polarized Luminescence

Abstract

Keywords

ASJC Scopus subject areas

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