Synthesis and Chiroptical Properties of Quinoxaline-Fused Polyaza[5]–[7]helicenes with Orange-Color CPL Emissions

Takashi Otani; Takuma Sasayama; Masashi Horiuchi; Shunnosuke Okauchi; Hidetoshi Kawai; Maho Kitahara; Yoshitane Imai; Takanori Shibata

doi:10.1002/hlca.202100016

Synthesis and Chiroptical Properties of Quinoxaline-Fused Polyaza[5]–[7]helicenes with Orange-Color CPL Emissions

Takashi Otani^*, Takuma Sasayama, Masashi Horiuchi, Shunnosuke Okauchi, Hidetoshi Kawai, Maho Kitahara, Yoshitane Imai, Takanori Shibata^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

3 Citations (Scopus)

Abstract

We achieved a two-type synthesis of quinoxaline-fused polyaza[5]- and [7]helicenes through consecutive N−H/C−H coupling with a hypervalent iodine reagent as a key reaction. By fusing electron-deficient quinoxaline, these polyazahelicenes constitute an efficient donor-acceptor type of molecule with absorption edges that reach up to approximately 650 nm. Evaluating the chiroptical properties reveals that the polyazahelicene exhibits a rare orange circularly polarized glow with a luminescence dissymmetry factor (g_lum value) of 0.003.

Original language	English
Article number	e2100016
Journal	Helvetica Chimica Acta
Volume	104
Issue number	4
DOIs	https://doi.org/10.1002/hlca.202100016
Publication status	Published - 2021 Apr

Keywords

N−H/C−H coupling
circularly polarized luminescence
electron-deficient compounds
helicenes
hypervalent compounds
quinoxalines

ASJC Scopus subject areas

Catalysis
Biochemistry
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1002/hlca.202100016

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title = "Synthesis and Chiroptical Properties of Quinoxaline-Fused Polyaza[5]–[7]helicenes with Orange-Color CPL Emissions",

abstract = "We achieved a two-type synthesis of quinoxaline-fused polyaza[5]- and [7]helicenes through consecutive N−H/C−H coupling with a hypervalent iodine reagent as a key reaction. By fusing electron-deficient quinoxaline, these polyazahelicenes constitute an efficient donor-acceptor type of molecule with absorption edges that reach up to approximately 650 nm. Evaluating the chiroptical properties reveals that the polyazahelicene exhibits a rare orange circularly polarized glow with a luminescence dissymmetry factor (glum value) of 0.003.",

keywords = "N−H/C−H coupling, circularly polarized luminescence, electron-deficient compounds, helicenes, hypervalent compounds, quinoxalines",

author = "Takashi Otani and Takuma Sasayama and Masashi Horiuchi and Shunnosuke Okauchi and Hidetoshi Kawai and Maho Kitahara and Yoshitane Imai and Takanori Shibata",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Number 16 K05710 and Waseda University Grant for Special Research projects (2020 N‐007). We acknowledge . for a generous gift of HFIP. Central Glass Co., Ltd Funding Information: This work was supported by JSPS KAKENHI Grant Number 16 K05710 and Waseda University Grant for Special Research projects (2020 N-007). We acknowledge Central Glass Co., Ltd. for a generous gift of HFIP. Publisher Copyright: {\textcopyright} 2021 Wiley-VHCA AG, Zurich, Switzerland",

year = "2021",

month = apr,

doi = "10.1002/hlca.202100016",

language = "English",

volume = "104",

journal = "Helvetica Chimica Acta",

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T1 - Synthesis and Chiroptical Properties of Quinoxaline-Fused Polyaza[5]–[7]helicenes with Orange-Color CPL Emissions

AU - Otani, Takashi

AU - Sasayama, Takuma

AU - Horiuchi, Masashi

AU - Okauchi, Shunnosuke

AU - Kawai, Hidetoshi

AU - Kitahara, Maho

AU - Imai, Yoshitane

AU - Shibata, Takanori

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Number 16 K05710 and Waseda University Grant for Special Research projects (2020 N‐007). We acknowledge . for a generous gift of HFIP. Central Glass Co., Ltd Funding Information: This work was supported by JSPS KAKENHI Grant Number 16 K05710 and Waseda University Grant for Special Research projects (2020 N-007). We acknowledge Central Glass Co., Ltd. for a generous gift of HFIP. Publisher Copyright: © 2021 Wiley-VHCA AG, Zurich, Switzerland

PY - 2021/4

Y1 - 2021/4

N2 - We achieved a two-type synthesis of quinoxaline-fused polyaza[5]- and [7]helicenes through consecutive N−H/C−H coupling with a hypervalent iodine reagent as a key reaction. By fusing electron-deficient quinoxaline, these polyazahelicenes constitute an efficient donor-acceptor type of molecule with absorption edges that reach up to approximately 650 nm. Evaluating the chiroptical properties reveals that the polyazahelicene exhibits a rare orange circularly polarized glow with a luminescence dissymmetry factor (glum value) of 0.003.

AB - We achieved a two-type synthesis of quinoxaline-fused polyaza[5]- and [7]helicenes through consecutive N−H/C−H coupling with a hypervalent iodine reagent as a key reaction. By fusing electron-deficient quinoxaline, these polyazahelicenes constitute an efficient donor-acceptor type of molecule with absorption edges that reach up to approximately 650 nm. Evaluating the chiroptical properties reveals that the polyazahelicene exhibits a rare orange circularly polarized glow with a luminescence dissymmetry factor (glum value) of 0.003.

KW - N−H/C−H coupling

KW - circularly polarized luminescence

KW - electron-deficient compounds

KW - helicenes

KW - hypervalent compounds

KW - quinoxalines

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JO - Helvetica Chimica Acta

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Synthesis and Chiroptical Properties of Quinoxaline-Fused Polyaza[5]–[7]helicenes with Orange-Color CPL Emissions

Abstract

Keywords

ASJC Scopus subject areas

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