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Updated: Jun 29, 2025

Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry
Published on: March 4, 2021
Highly Contorted Rigid Nitrogen-Rich Nanographene with Four Heptagons
Abdusalom A Suleymanov1, Qilin He1, Peter Müller1
1Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.
Abstract:
Nucleophilic substitution of 9,10-dichlorooctafluoroanthracene with 3,4-diethylpyrrole and subsequent Scholl reaction give the annularly fused decapyrrollyl anthracene. Single crystal X-ray analysis revealed a highly contorted geometry induced by a combination of adjacent heptagons, forming a unique 7-7-6-7-7 topology. The end-to-end twist angle along the acene moiety is 90°. Cyclic voltammetry studies reveal 6-electron oxidation waves. Density functional theory calculations provided further insights into the aromaticity and electronic properties of this highly twisted, nitrogen-rich nanographene. The structural rigidity and high racemization energy barrier have been studied theoretically and experimentally by VT-NMR.
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