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- Title
Facile Two-Step Synthesis of 1,10-Phenanthroline-Derived Polyaza[7]helicenes with High Fluorescence and CPL Efficiency.
- Authors
Tsuyuki, Ami; Someya, Satoshi; Otani, Takashi; Shibata, Takanori; Saito, Takao; Iwachi, Taiki; Tateno, Kotaro; Kawai, Hidetoshi; Kanyiva, Kyalo Stephen
- Abstract
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).
- Subjects
HELICENES; FLUORESCENCE yield; LUMINESCENCE; CHIRALITY; PHENANTHROLINE; ANILINE derivatives
- Publication
Angewandte Chemie International Edition, 2017, Vol 56, Issue 14, p3906
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201700507