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

Autor: Tan J; College of Chemistry and Chemical Engineering, Central South University, 410083, Changsha, China.; Organic and Carbon Nanomaterials Unit, Okinawa Institute of Science and Technology Graduate University, 1919-1 Tancha, Onna-son, Kunigami-gun, Okinawa, 904-0495, Japan., Xu X; Organic and Carbon Nanomaterials Unit, Okinawa Institute of Science and Technology Graduate University, 1919-1 Tancha, Onna-son, Kunigami-gun, Okinawa, 904-0495, Japan., Liu J; College of Chemistry and Chemical Engineering, Central South University, 410083, Changsha, China., Vasylevskyi S; Engineering Section, Research Support Division, Okinawa Institute of Science and Technology Graduate University, 1919-1 Tancha, Onna-son, Kunigami-gun, Okinawa, 904-0495, Japan., Lin Z; Organic Optoelectronics Unit, Okinawa Institute of Science and Technology Graduate University, 1919-1 Tancha, Onna-son, Kunigami-gun, Okinawa, 904-0495, Japan., Kabe R; Organic Optoelectronics Unit, Okinawa Institute of Science and Technology Graduate University, 1919-1 Tancha, Onna-son, Kunigami-gun, Okinawa, 904-0495, Japan., Zou Y; College of Chemistry and Chemical Engineering, Central South University, 410083, Changsha, China., Müllen K; Max Planck Institute for Polymer Research, 55128, Mainz, Germany., Narita A; Organic and Carbon Nanomaterials Unit, Okinawa Institute of Science and Technology Graduate University, 1919-1 Tancha, Onna-son, Kunigami-gun, Okinawa, 904-0495, Japan., Hu Y; College of Chemistry and Chemical Engineering, Central South University, 410083, Changsha, China.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2023 Apr 24; Vol. 62 (18), pp. e202218494. Date of Electronic Publication: 2023 Mar 22.
DOI: 10.1002/anie.202218494
Abstrakt: 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.
(© 2023 Wiley-VCH GmbH.)
Databáze: MEDLINE
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