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Synthesis of a π-Extended Double [9]Helicene.

Jingyun TanXiushang XuJun LiuSerhii I VasylevskyiZesen LinRyota KabeYingping ZouKlaus MüllenAkimitsu NaritaYingping Zou
Published in: Angewandte Chemie (International ed. in English) (2023)
Double helicenes are appealing chiral frameworks. Their π-extension is desirable to achieve (chir)optical response in the visible and near-infrared (NIR) region, but access to higher double [n]helicenes (n≥8) has remained challenging. Herein, we report an unprecedented π-extended double [9]helicene (D9H), unambiguously revealing its structure by single-crystal X-ray diffraction. D9H shows remarkable NIR emission from 750 to 1100 nm with a high photoluminescence quantum yield of 18 %. In addition, optically pure D9H exhibits panchromatic circular dichroism with a notable dissymmetry factor (g CD ) of 0.019 at 590 nm, which is among the highest in the visible region for reported helicenes.
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