ArticleChemical science2023
Helical fused 1,2:8,9-dibenzozethrene oligomers with up to 201° end-to-end twist: "one-pot" synthesis and chiral resolution.
Article in Chemical science, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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4 citing papers in PubMed.
- Isomeric Dibenzodiindenophenanthrene Diradicaloids: Synthesis, Structures, Properties, and Efficient NIR Photothermal Conversion for Imaging.Angewandte Chemie (International ed. in English) · 2026Article
- On Diphenalenes Comprising Seven Hexagonal Rings.ACS omega · 2025Article
- Helical polycyclic hydrocarbons with open-shell singlet ground states and ambipolar redox behaviors.Chemical science · 2024Article
- NIR-II photothermal conversion and imaging based on a cocrystal containing twisted components.Chemical science · 2024Article
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Authors and funding
10 authors.
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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.
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