Multifunctional Octamethyltetrasila[2.2]cyclophanes: Conformational Variations, Circularly Polarized Luminescence, and Organic Electroluminescence

Masaki Shimada, Yoshinori Yamanoi*, Tatsuhiko Ohto, Song Toan Pham, Ryo Yamada, Hirokazu Tada, Kenichiro Omoto, Shohei Tashiro, Mitsuhiko Shionoya, Mineyuki Hattori, Keiko Jimura, Shigenobu Hayashi, Hikaru Koike, Munetaka Iwamura, Koichi Nozaki, 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

76 被引用数 (Scopus)

抄録

Both symmetrical and unsymmetrical cyclophanes containing disilane units, tetrasila[2.2]cyclophanes 1-9, were synthesized. The syn and anti conformations and the kinetics of inversion between two anti-isomers were investigated by X-ray diffraction and variableerature NMR analysis, respectively. The flipping motion of two aromatic rings was affected by the bulkiness of the aromatic moiety (1 vs 6), the phase (solid vs solution), and the inclusion by host molecules (1 vs 1?[Ag2L]2+). The photophysical, electrochemical, and structural properties of the compounds were thoroughly investigated. Unsymmetrical tetrasila[2.2]cyclophanes 5-8 displayed blue-green emission arising from intramolecular charge transfer. Compound 6 emitted a brilliant green light in the solid state under 365 nm irradiation and showed a higher fluorescence quantum yield in the solid state (φ = 0.49) than in solution (φ = 0.05). We also obtained planar chiral tetrasila[2.2]cyclophane 9, which showed interesting chiroptical properties, such as a circularly polarized luminescence (CPL) with a dissymmetry factor of |glum| = ca. 2 × 10-3 at 500 nm. Moreover, an organic green light-emitting diode that showed a maximum external quantum efficiency (next) of ca. 0.4% was fabricated by doping 4,4′-bis(2,2′-diphenylvinyl)-1,1′-biphenyl with 6.

本文言語英語
ページ(範囲)11214-11221
ページ数8
ジャーナルJournal of the American Chemical Society
139
32
DOI
出版ステータス出版済み - 2017/08/16

ASJC Scopus 主題領域

  • 触媒
  • 化学一般
  • 生化学
  • コロイド化学および表面化学

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