1,2,3-Triarylazulenes as precursors of azulene-embedded polycyclic aromatic hydrocarbons

A series of 1,2,3-triarylazulenes was obtained using new synthetic methodology and subsequently subjected to Scholl-type oxidation aiming for conjugated azulene-embedded polycyclic aromatic hydrocarbons (PAHs). The oxidation yielded either unexpected azulen-1(8aH)-ones or desired purely hydrocarbon...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2024-10, Vol.11 (21), p.6026-6035
Main Authors: Biesaga, Justyna, Szafert, Sławomir, Pigulski, Bartłomiej
Format: Article
Language:English
Subjects:
Azulene
Electrochemistry
Electronic structure
Energy gap
Near infrared radiation
Optical properties
Oxidation
Polycyclic aromatic hydrocarbons
Substitution reactions
Topology
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Summary:A series of 1,2,3-triarylazulenes was obtained using new synthetic methodology and subsequently subjected to Scholl-type oxidation aiming for conjugated azulene-embedded polycyclic aromatic hydrocarbons (PAHs). The oxidation yielded either unexpected azulen-1(8aH)-ones or desired purely hydrocarbon azulene-embedded PAHs, depending on the substitution pattern. Different reaction pathways were rationalized using DFT calculations, leading to the observation that 2-pyrenyl substituents facilitate formation of the desired conjugated molecules. The fully hydrocarbon azulene-embedded PAHs exhibit a relatively small electrochemical energy gap below 2 eV and optical absorption reaching the near-infrared (NIR) region. These properties are attributed to their non-alternant topology and retained azulene-like electronic structure.
ISSN:2052-4110
2052-4110
DOI:10.1039/d4qo01459f