Dioxacyclophanes as a Scaffold for Silicon-based Circularly Polarized Luminescent Materials

Yoshinori Yamanoi*, Tsukasa Usuki, Kenichiro Omoto, Masaki Shimada, Hikaru Koike, Munetaka Iwamura, Koichi Nozaki, Daisuke Saito, Masako Kato, Hiroshi Nishihara

*この論文の責任著者

研究成果: ジャーナルへの寄稿学術論文査読

1 被引用数 (Scopus)

抄録

Planar chiral dioxacyclophanes were designed and synthesized as a key scaffold for materials with circularly polarized luminescence (CPL). Representative planar chiral 1,12-dioxa[12](1,4)naphthaleneophane-derived organosilane compounds (−)-(R)-1, (+)-(R)-2, and (−)-(R)-3 were prepared by (+)-sparteine-mediated aryl metalation and an electrophilic reaction with chlorosilanes. The absolute configurations of the planar chirality were determined in the R form by single-crystal X-ray analysis. Optically active compound (+)-(R)-2 exhibited blue fluorescence and a CPL signal with a dissymmetry factor (g lum value) of 0.001 in solution. The electronic structure was corroborated by DFT and TD-DFT calculations rationalizing the observed spectroscopic properties.

本文言語英語
ページ(範囲)1108-1112
ページ数5
ジャーナルTetrahedron Letters
60
16
DOI
出版ステータス出版済み - 2019/04/18

ASJC Scopus 主題領域

  • 生化学
  • 創薬
  • 有機化学

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