Internal-Edge-Substituted Coumarin-Fused [6]Helicenes: Asymmetric Synthesis, Structural Features, and Control of Self-Assembly

Kazuteru Usui, Kosuke Yamamoto, Yuhei Ueno, Kazunobu Igawa, Ryusuke Hagihara, Toshinobu Masuda, Akio Ojida, Satoru Karasawa, Katsuhiko Tomooka, Go Hirai, Hiroshi Suemune

研究成果: ジャーナルへの寄稿記事

2 引用 (Scopus)

抄録

π-Conjugated helicenes containing heteroatoms have attracted significant attention due to their diverse chemical and electronic structures, as well as tunable physical properties. It was rationally anticipated that the self-assembly of coumarin-fused helicenes would be controlled by the effects of a substituent on the internal edge of the helix. Here, this work reports the efficient syntheses of coumarin-fused helicenes 1 a,b (R=Ph, Me), and the enantioselective synthesis of 1 a (R=Ph) by chiral AuI-catalyzed hydroarylation. The helical structure of 1 was unambiguously determined by X-ray crystallography. Of particular note, the enantiomerically pure crystal of 1 a adopted a one-dimensional columnar structure based on π–π stacking interactions, as expected. Furthermore, a significant difference between the fluorescence quantum yields of the enantiomerically pure form and racemate of 1 a was observed.

元の言語英語
ページ(範囲)14617-14621
ページ数5
ジャーナルChemistry - A European Journal
24
発行部数55
DOI
出版物ステータス出版済み - 10 1 2018

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Self assembly
X ray crystallography
Quantum yield
Electronic structure
Physical properties
Fluorescence
Crystals
helicenes
coumarin

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

これを引用

Internal-Edge-Substituted Coumarin-Fused [6]Helicenes : Asymmetric Synthesis, Structural Features, and Control of Self-Assembly. / Usui, Kazuteru; Yamamoto, Kosuke; Ueno, Yuhei; Igawa, Kazunobu; Hagihara, Ryusuke; Masuda, Toshinobu; Ojida, Akio; Karasawa, Satoru; Tomooka, Katsuhiko; Hirai, Go; Suemune, Hiroshi.

:: Chemistry - A European Journal, 巻 24, 番号 55, 01.10.2018, p. 14617-14621.

研究成果: ジャーナルへの寄稿記事

Usui, Kazuteru ; Yamamoto, Kosuke ; Ueno, Yuhei ; Igawa, Kazunobu ; Hagihara, Ryusuke ; Masuda, Toshinobu ; Ojida, Akio ; Karasawa, Satoru ; Tomooka, Katsuhiko ; Hirai, Go ; Suemune, Hiroshi. / Internal-Edge-Substituted Coumarin-Fused [6]Helicenes : Asymmetric Synthesis, Structural Features, and Control of Self-Assembly. :: Chemistry - A European Journal. 2018 ; 巻 24, 番号 55. pp. 14617-14621.
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AU - Ueno, Yuhei

AU - Igawa, Kazunobu

AU - Hagihara, Ryusuke

AU - Masuda, Toshinobu

AU - Ojida, Akio

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