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).
| Original language | English |
|---|---|
| Pages (from-to) | 3906-3910 |
| Number of pages | 5 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 56 |
| Issue number | 14 |
| DOIs | |
| Publication status | Published - 2017 Mar 27 |
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Keywords
- azahelicene
- circularly polarized luminescence
- fluorescence
- oxidative coupling
- X-ray diffraction
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
Cite this
Facile Two-Step Synthesis of 1,10-Phenanthroline-Derived Polyaza[7]helicenes with High Fluorescence and CPL Efficiency. / Otani, Takashi; Tsuyuki, Ami; Iwachi, Taiki; Someya, Satoshi; Tateno, Kotaro; Kawai, Hidetoshi; Saito, Takao; Kanyiva, Stephen Kyalo; Shibata, Takanori.
In: Angewandte Chemie - International Edition, Vol. 56, No. 14, 27.03.2017, p. 3906-3910.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Facile Two-Step Synthesis of 1,10-Phenanthroline-Derived Polyaza[7]helicenes with High Fluorescence and CPL Efficiency
AU - Otani, Takashi
AU - Tsuyuki, Ami
AU - Iwachi, Taiki
AU - Someya, Satoshi
AU - Tateno, Kotaro
AU - Kawai, Hidetoshi
AU - Saito, Takao
AU - Kanyiva, Stephen Kyalo
AU - Shibata, Takanori
PY - 2017/3/27
Y1 - 2017/3/27
N2 - 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).
AB - 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).
KW - azahelicene
KW - circularly polarized luminescence
KW - fluorescence
KW - oxidative coupling
KW - X-ray diffraction
UR - http://www.scopus.com/inward/record.url?scp=85014734420&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85014734420&partnerID=8YFLogxK
U2 - 10.1002/anie.201700507
DO - 10.1002/anie.201700507
M3 - Article
VL - 56
SP - 3906
EP - 3910
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 14
ER -