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Title: Helical fused 1,2:8,9-dibenzozethrene oligomers with up to 201° end-to-end twist: "one-pot" synthesis and chiral resolution
Authors: Sun, Zhitao
Fan, Wei
Han, Yi
Yuan, Wei
Ni, Yong
Wang, Jinyi
Wei, Haipeng
Zhao, Yanli
Sun, Zhe
Wu, Jishan
Keywords: Science::Chemistry
Issue Date: 2023
Source: Sun, Z., Fan, W., Han, Y., Yuan, W., Ni, Y., Wang, J., Wei, H., Zhao, Y., Sun, Z. & Wu, J. (2023). Helical fused 1,2:8,9-dibenzozethrene oligomers with up to 201° end-to-end twist: "one-pot" synthesis and chiral resolution. Chemical Science, 14(29), 7922-7927.
Journal: Chemical Science 
Abstract: Twisted polyarenes with persistent chirality are desirable but their synthesis has remained a challenge. In this study, we present a "one-pot" synthesis of 1,2:8,9-dibenzozethrene (DBZ) and its vertically fused dimers and trimers using nickel-catalyzed cyclo-oligomerization reactions. X-ray crystallographic analysis confirmed highly twisted helical structures that consist of equal parts left- and right-handed enantiomers. Notably, the end-to-end twist between the terminal anthracene units measured 66°, 130°, and 201° for the DBZ monomer, dimer, and trimer, respectively, setting a new record among twisted polyarenes. Furthermore, the chiral resolution by HPLC yielded two enantiomers for the fused DBZ dimer and trimer, both of which maintained stable configurations and showed absorption dissymmetry factors of around 0.008-0.009. Additionally, their optical and electrochemical properties were investigated, which exhibited a chain-length dependence.
ISSN: 2041-6520
DOI: 10.1039/d3sc02285d
Schools: School of Chemistry, Chemical Engineering and Biotechnology 
Rights: © 2023 The Author(s). Published by the Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:CCEB Journal Articles

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