Protonation-induced red-coloured circularly polarized luminescence of [5]carbohelicene fused by benzimidazole

Hayato Sakai; Takako Kubota; Junpei Yuasa; Yasuyuki Araki; Tomo Sakanoue; Taishi Takenobu; Takehiko Wada; Tsuyoshi Kawai; Taku Hasobe

doi:10.1039/c6ob00937a

Protonation-induced red-coloured circularly polarized luminescence of [5]carbohelicene fused by benzimidazole

Hayato Sakai, Takako Kubota, Junpei Yuasa, Yasuyuki Araki, Tomo Sakanoue, Taishi Takenobu, Takehiko Wada, Tsuyoshi Kawai, Taku Hasobe

Department of Chemistry

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

34 Citations (Scopus)

Abstract

Benzimidazole-fused [5]carbohelicene ([5]HeliBI) was newly synthesized to examine the spectroscopic and chiroptical properties. The reversible protonation and deprotonation processes of [5]HeliBI were successfully investigated using ¹H NMR, absorption and fluorescence spectral measurements. We also confirmed the circularly polarized luminescence of protonated [5]HeliBI (H⁺-[5]HeliBI). This is the first observation of red-coloured CPL of a helicene derivative.

Original language	English
Pages (from-to)	6738-6743
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	28
DOIs	https://doi.org/10.1039/c6ob00937a
Publication status	Published - 2016

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Protonation-induced red-coloured circularly polarized luminescence of [5]carbohelicene fused by benzimidazole",

abstract = "Benzimidazole-fused [5]carbohelicene ([5]HeliBI) was newly synthesized to examine the spectroscopic and chiroptical properties. The reversible protonation and deprotonation processes of [5]HeliBI were successfully investigated using 1H NMR, absorption and fluorescence spectral measurements. We also confirmed the circularly polarized luminescence of protonated [5]HeliBI (H+-[5]HeliBI). This is the first observation of red-coloured CPL of a helicene derivative.",

author = "Hayato Sakai and Takako Kubota and Junpei Yuasa and Yasuyuki Araki and Tomo Sakanoue and Taishi Takenobu and Takehiko Wada and Tsuyoshi Kawai and Taku Hasobe",

note = "Funding Information: This work was partially supported by JSPS KAKENHI Grant Numbers 26286017, JP16K14067, JP15H01003. Publisher Copyright: {\textcopyright} 2016 The Royal Society of Chemistry.",

year = "2016",

doi = "10.1039/c6ob00937a",

language = "English",

volume = "14",

pages = "6738--6743",

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T1 - Protonation-induced red-coloured circularly polarized luminescence of [5]carbohelicene fused by benzimidazole

AU - Sakai, Hayato

AU - Kubota, Takako

AU - Yuasa, Junpei

AU - Araki, Yasuyuki

AU - Sakanoue, Tomo

AU - Takenobu, Taishi

AU - Wada, Takehiko

AU - Kawai, Tsuyoshi

AU - Hasobe, Taku

PY - 2016

Y1 - 2016

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AB - Benzimidazole-fused [5]carbohelicene ([5]HeliBI) was newly synthesized to examine the spectroscopic and chiroptical properties. The reversible protonation and deprotonation processes of [5]HeliBI were successfully investigated using 1H NMR, absorption and fluorescence spectral measurements. We also confirmed the circularly polarized luminescence of protonated [5]HeliBI (H+-[5]HeliBI). This is the first observation of red-coloured CPL of a helicene derivative.

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JF - Organic and Biomolecular Chemistry

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ER -

Protonation-induced red-coloured circularly polarized luminescence of [5]carbohelicene fused by benzimidazole

Abstract

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