ArticleAngewandte Chemie (International ed. in English)2025
Rhodium-Catalyzed Intermolecular Arylative [2 + 2 + 1] Annulation-Oxidation to Produce Electron-Deficient Azulene-Embedded Polycyclic Aromatic Hydrocarbons.
Article in Angewandte Chemie (International ed. in English), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- 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
- Rhodium-Catalyzed Intermolecular Arylative [2 + 2 + 1] Annulation-Oxidation to Produce Electron-Deficient Azulene-Embedded Polycyclic Aromatic Hydrocarbons.Angewandte Chemie (International ed. in English) · 2025Article
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10 authors.
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Abstract
Azulene derivatives have attracted much attention for their application in organic electronic materials and devices because of their large dipole moment and small HOMO-LUMO energy gap. As these physical properties of azulene depend on its substitution and condensation patterns, developing methods to synthesize functionalized and π-extended azulenes is desirable. However, synthesizing π-extended azulenes requires harsh reaction conditions, making it hard to achieve both functionalization and π-extension. Here, we report the synthesis of electron-deficient azulene-embedded polycyclic aromatic hydrocarbons (PAHs) with two alkoxycarbonyl groups by the rhodium-catalyzed intermolecular arylative [2 + 2 + 1] annulation of teraryl diynes with dialkyl acetylenedicarboxylates followed by oxidation at room temperature. Interestingly, for the electron-rich diyne, prolonged oxidation time after the arylative [2 + 2 + 1] annulation yields a helicene-like bis(azulene-embedded PAH) in good yield. Thus, obtained electron-deficient fused azulenes have small HOMO-LUMO energy gaps (up to E
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