Modular Synthesis of Structurally Diverse Azulene‐Embedded Polycyclic Aromatic Hydrocarbons by Knoevenagel‐Type Condensation

Autor: Renxiang Liu, Yubin Fu, Fupeng Wu, Fupin Liu, Jin‐Jiang Zhang, Lin Yang, Alexey A. Popov, Ji Ma, Xinliang Feng
Rok vydání: 2023
Předmět:
Zdroj: Angewandte Chemie, International Edition in English
ISSN: 1521-3773
1433-7851
DOI: 10.1002/anie.202219091
Popis: The research interest in azulene-embedded polycyclic aromatic hydrocarbons (PAHs) has significantly increased recently, but the lack of efficient synthetic strategies impedes the investigation of their structure-property relationships and further opto-electronic applications. Here we report a modular synthetic strategy towards diverse azulene-embedded PAHs by a tandem Suzuki coupling and base-promoted Knoevenagel-type condensation with good yields and great structural versatility, including non-alternant thiophene-rich PAHs, butterfly- or Z-shaped PAHs bearing two azulene units, and the first example of a two-azulene-embedded double [5]helicene. The structural topology, aromaticity and photophysical properties were investigated by NMR, X-ray crystallography analysis and UV/Vis absorption spectroscopy assisted by DFT calculations. This strategy provides a new platform for rapidly synthesizing unexplored non-alternant PAHs or even graphene nanoribbons with multiple azulene units.
Databáze: OpenAIRE
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