ArticleAngewandte Chemie (International ed. in English)2022
Oxidative Cyclodehydrogenation of Trinaphthylamine: Selective Formation of a Nitrogen-Centered Polycyclic π-System Comprising 5- and 7-Membered Rings.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 23 citations in OpenAlex.
- Highly Emissive Double π-Helical Molecular Carbons via Nitrogen Integration.Angewandte Chemie (International ed. in English) · 2026Article
- N-Doped Nonalternant Molecular Bowl/Saddle Hybrids.Angewandte Chemie (International ed. in English) · 2025Article
- The degradation mechanism of multi-resonance thermally activated delayed fluorescence materials.Nature communications · 2025Article
- Cycl[2,2,4]azine-embedded non-alternant nanographenes containing fused antiaromatic azepine ring.Chemical science · 2024Article
- Oxidative Cyclodehydrogenation of Trinaphthylamine: Selective Formation of a Nitrogen-Centered Polycyclic π-System Comprising 5- and 7-Membered Rings.Angewandte Chemie (International ed. in English) · 2022Article
Corrections and comments
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Authors and funding
12 authors at 3 institutions in 2 countries.
Funding
Abstract
We describe a new type of nitrogen-centered polycyclic scaffold comprising a unique combination of 5-, 6-, and 7-membered rings. The compound is accessible through an intramolecular oxidative cyclodehydrogenation of tri(1-naphthyl)amine. To the best of our knowledge this is the very first example of a direct 3-fold cyclization of a triarylamine under oxidative conditions. The unusual ring fusion motif is confirmed by X-ray crystallography and the impact of cyclization on the electronic and photophysical properties is investigated both experimentally and theoretically based on density-functional theory (DFT) calculations. The formation of the unexpected product is rationalized by detailed mechanistic studies on the DFT level. The results suggest the cyclization to occur under kinetic control via a dicationic mechanism.
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Registered trials
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