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https://doi.org/https://onlinelibrary.wiley.com/doi/10.1002/anie.202218090
Title: | Facile Synthesis and Chiral Resolution of Expanded Helicenes with up to 35 cata-Fused Benzene Rings | Authors: | Shaofei Wu Guifei Huo Toshiya M. Fukunaga Xudong Hou Wei Fan Hiroyuki Isobe Jishan Wu |
Keywords: | Benzannulation Chiral Molecules Circular Dichroism Expanded Helicenes Polyarenes |
Issue Date: | 24-Apr-2023 | Citation: | Shaofei Wu, Guifei Huo, Toshiya M. Fukunaga, Xudong Hou, Wei Fan, Hiroyuki Isobe, Jishan Wu (2023-04-24). Facile Synthesis and Chiral Resolution of Expanded Helicenes with up to 35 cata-Fused Benzene Rings. Angewandte Chemie International Edition 62 (18) : e202218090. ScholarBank@NUS Repository. https://doi.org/https://onlinelibrary.wiley.com/doi/10.1002/anie.202218090 | Rights: | Attribution-NonCommercial-NoDerivatives 4.0 International | Abstract: | Expanded helicenes are expected to show enhanced chiroptical properties as compared to the classical helicenes but the synthesis is very challenging. Herein, we report the facile synthesis of a series of expanded helicenes Hn (n=1–4) containing 11, 19, 27 and 35 cata-fused benzene rings through Suzuki coupling-based oligomerization followed by Bi(OTf)3-mediated regioselective cyclization of vinyl ethers. Their structures were determined by X-ray crystallographic analysis. Enantiopure H2, H3, and H4 can be isolated by chiral HPLC and they all exhibit strong chiroptical responses with high absorption dissymmetry factor (j gabs j) values (0.020 for H2, 0.021 for H3, and 0.021–0.024 for H4). | Source Title: | Angewandte Chemie International Edition | URI: | https://scholarbank.nus.edu.sg/handle/10635/249727 | ISSN: | 1433-7851 1521-3773 |
DOI: | https://onlinelibrary.wiley.com/doi/10.1002/anie.202218090 | Rights: | Attribution-NonCommercial-NoDerivatives 4.0 International |
Appears in Collections: | Staff Publications Elements |
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