ArticleNature chemistry2023
Tetrafluorenofulvalene as a sterically frustrated open-shell alkene.
Article in Nature chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed, 29 citations in OpenAlex.
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- Backbone Engineering of Carbon-Centered NHC-Derived Diradicals: From Electronic State Tuning to High-Performance Organic Field-Effect Transistors.Advanced materials (Deerfield Beach, Fla.) · 2026Article
- The interplay of antiaromaticity and diradical character in diarenoindacenes and diindenoarenes.Chemical science · 2025Review
- Solution-phase synthesis of Clar's goblet and elucidation of its spin properties.Nature chemistry · 2025Article
- Diverse redox-mediated transformations to realize the para-quinoid, σ-bond, and ortho-diphenoquinoid forms.Nature communications · 2025Article
- Enhancing the Optically Detected Magnetic Resonance Signal of Organic Molecular Qubits.ACS central science · 2025Article
- 6,6'-Biindeno[1,2-Chemical science · 2024Article
- Difluorenoheteroles: topological control of π conjugation in diradicaloids and mixed-valence radical ions.Chemical science · 2024Article
- An open-shell molecule that exhibits conformational dynamics.Nature chemistry · 2023Article
- Synthesis, structural analysis, and properties of highly twisted alkenes 13,13'-bis(dibenzo[a,i]fluorenylidene) and its derivatives.Nature communications · 2023Article
Corrections and comments
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Authors and funding
8 authors at 3 institutions in 3 countries.
Funding
Abstract
Electronic and steric effects are known to greatly influence the structure, characteristics and reactivity of organic compounds. A typical π bond is weakened by oxidation (corresponding to the removal of electrons from bonding orbitals), by reduction (through addition of electrons to antibonding orbitals) and by unpairing of the bonding electrons, such as in the triplet state. Here we describe tetrafluorenofulvalene (TFF), a twisted, open-shell alkene for which these general rules do not hold. Through the synthesis, experimental characterization and computational analysis of its charged species spanning seven redox states, the central alkene bond in TFF is shown to become substantially stronger in the tri- and tetraanion, generated by chemical reduction. Furthermore, although its triplet state contains a weaker alkene bond than the singlet, in the quintet state its bond order increases substantially, yielding a flatter structure. This behaviour originates from the doubly bifurcated topology of the underlying spin system and can be rationalized by the balancing effects of benzenoid aromaticity and spin pairing.
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