Facile Two-Step Synthesis of 1,10-Phenanthroline-Derived Polyaza[7]helicenes with High Fluorescence and CPL Efficiency

Takashi Otani, Ami Tsuyuki, Taiki Iwachi, Satoshi Someya, Kotaro Tateno, Hidetoshi Kawai, Takao Saito, Kyalo Stephen Kanyiva, Takanori Shibata

研究成果: Article査読

63 被引用数 (Scopus)

抄録

A facile two-step synthesis of aza[7]helicenes possessing a 6-5-6-6-6-5-6 skeleton from commercially available 2,9-dichloro-1,10-phenanthroline via double amination with aniline derivatives followed by hypervalent iodine reagent-mediated intramolecular double-NH/CH couplings was developed. Single-crystal X-ray analyses of the helicenes revealed unique structures, including both a significantly twisted center and planar terminals of the skeleton. The azahelicenes show high fluorescent quantum yields (Φs) under both neutral (Φ: 0.25–0.55) and acidic conditions (Φ: up to 0.80). An enantiomerically pure aza[7]helicene showed high circularly polarized luminescence (CPL) activity under both neutral and acidic conditions (glum: up to 0.009).

本文言語English
ページ(範囲)3906-3910
ページ数5
ジャーナルAngewandte Chemie - International Edition
56
14
DOI
出版ステータスPublished - 2017

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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