ArticleChemistry (Weinheim an der Bergstrasse, Germany)2026
Azulene-Fused Polycyclic Aromatic Hydrocarbons: Synthesis, Structural, Optical, and Electrochemical Properties of Azuleno[1,2,3-cd]Benzo[mn]Pyrene-8,14-diones and Cyclohepta[1,2]Indeno[6,5,4-de]Anthracen-9-ones.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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3 citing papers in PubMed.
- Synthesis of azulene fluorophores reveals structure-property relationships.Organic chemistry frontiers : an international journal of organic chemistry · 2026Article
- Azulene-Fused Polycyclic Aromatic Hydrocarbons: Synthesis, Structural, Optical, and Electrochemical Properties of Azuleno[1,2,3-cd]Benzo[mn]Pyrene-8,14-diones and Cyclohepta[1,2]Indeno[6,5,4-de]Anthracen-9-ones.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Huisgen Cycloaddition of Azidoazulenes: Synthesis, Structural and Optical Properties of 2- and 6-(1,2,3-Triazol-1-yl)azulenes.Molecules (Basel, Switzerland) · 2026Article
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7 authors.
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Abstract
We report a modular synthesis of anthracene-based azulene-fused polycyclic aromatic hydrocarbons (PAHs) from 2-chloroazulenes via Suzuki-Miyaura coupling with 9-anthracenyl organoboron reagents, followed by Brønsted acid-promoted intramolecular annulation. The cyclization pathway was significantly influenced by the reaction medium: Eaton's reagent afforded doubly annulated products, whereas methanesulfonic acid preferentially gave mono-cyclized products through the annulation accompanied by decarboxylation. In one notable case, additional Scholl-type cyclization resulted in the formation of a more extensively fused naphtho[2,1-a]aceanthrylene analogue. Spectroscopic, crystallographic, and TD-DFT studies revealed that the appended 10-aryl substituents adopt orientations that are almost perpendicular to the fused core. This means that they have little influence on the neutral-state frontier electronic structure. Accordingly, most derivatives showed similar visible absorption profiles, whereas naphtho[2,1-a]aceanthrylene analogue exhibited substantially red-shifted absorption because of its expanded fused π-system. Under acidic conditions, both series displayed pronounced halochromic and fluorochromic behavior, including long-wavelength to near-infrared emission, and
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