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CC BY 4.0 · Organic Materials 2023; 05(04): 202-206
DOI: 10.1055/a-2172-1216
Short Communication

Synthesis of Polycyclic Aromatic Hydrocarbons with Highly Twisted N-Doped Heptalene

Shuhai Qiu 
a   Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. of China
,
Junzhi Liu 
a   Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. of China
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Abstract

A series of N-doped heptalene-containing polycyclic aromatic hydrocarbons (PAHs) have been synthesized and characterized in comparison with the N-doped azulene analogs. The crystal structure revealed its highly twisted geometry with a dihedral angle of 105.7° in the cove region of the N-doped dibenzoheptalene backbone. In addition, the electronic structure was both theoretically and experimentally investigated compared with the PAH bearing N-doped azulene unit. Our study provides a new synthetic strategy towards N-doped heptalene-embedded PAHs, and gives insights into the electronic properties of novel π-systems with N-doped nonalternant topologies.

Key words

heptalene - nitrogen doping - non-alternant PAHs - optical properties - fluorescence

Supporting Information



Publication History

Received: 03 July 2023

Accepted after revision: 30 August 2023

Accepted Manuscript online:
08 September 2023

Article published online:
12 December 2023

© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/).

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