ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
Cations and Anions of Dibenzo[a,e]pentalene and Reduction of a Dibenzo[a,e]pentalenophane.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- TetrahedralJACS Au · 2026Article
- Modular synthesis of benzothiophene-fused pentalenes reveals substituent-dependent antiaromaticity.Chemical science · 2026Article
- Concealed antiaromaticity.Open research Europe · 2025Article
- Towards clustered carbonyl cations [MChemical science · 2022Article
- Enantiopure nanohoops through racemic resolution of diketo[Chemical science · 2021Article
- Conjugated Nanohoops Incorporating Donor, Acceptor, Hetero- or Polycyclic Aromatics.Angewandte Chemie (International ed. in English) · 2021Review
- Chiral Dibenzopentalene-Based Conjugated Nanohoops through Stereoselective Synthesis.Angewandte Chemie (International ed. in English) · 2021Article
- Cations and Anions of Dibenzo[a,e]pentalene and Reduction of a Dibenzo[a,e]pentalenophane.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
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7 authors.
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Abstract
Dibenzo[a,e]pentalene (DBP) is a non-alternant conjugated hydrocarbon with antiaromatic character and ambipolar electrochemical behavior. Upon both reduction and oxidation, it becomes aromatic. We herein study the chemical oxidation and reduction of a planar DBP derivative and a bent DBP-phane. The molecular structures of its planar dication, cation radical and anion radical in the solid state demonstrate the gained aromaticity through bond length equalization, which is supported by nucleus independent chemical shift-calculations. EPR spectra on the cation radical confirm the spin delocalization over the DBP framework. A similar delocalization was not possible in the reduced bent DBP-phane, which stabilized itself by proton abstraction from a solvent molecule upon reduction. This is the first report on structures of a DBP cation radical and dication in the solid state and of a reduced bent DBP derivative. Our study provides valuable insight into the charged species of DBP for its application as semiconductor.
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