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CC BY 4.0 · Organic Materials 2023; 05(04): 202-206
DOI: 10.1055/a-2172-1216
DOI: 10.1055/a-2172-1216
Short Communication
Synthesis of Polycyclic Aromatic Hydrocarbons with Highly Twisted N-Doped Heptalene
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.
Publikationsverlauf
Eingereicht: 03. Juli 2023
Angenommen nach Revision: 30. August 2023
Accepted Manuscript online:
08. September 2023
Artikel online veröffentlicht:
12. Dezember 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/).
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
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- 19 The UV-Vis spectroscopy was performed on the Agilent Cary 60. The photoluminescence spectra were measured on Cary Eclipse Fluorescence Spectrofluorometer, Agilent Cary G9800AA. Cyclic voltammetry (CV) measurements were carried out on a CHI660E (CH Instruments, USA) in a three-electrode cell in an anhydrous dichloromethane (DCM) solution of tetrabutylammonium hexafluorophosphate (n-Bu4NPF6, 0.1 M) with a scan rate of 100 mV/s at room temperature. All potentials were further calibrated against ferrocene/ferrocenium (Fc/Fc+).