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A persistent concealed non-Kekulé nanographene: synthesis and in situ characterization

MPS-Authors
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Imran,  Muhammad       
Department of Synthetic Materials and Functional Devices (SMFD), Max Planck Institute of Microstructure Physics, Max Planck Society;

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Yang,  Lin
Department of Synthetic Materials and Functional Devices (SMFD), Max Planck Institute of Microstructure Physics, Max Planck Society;

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Zhang,  Jin-Jiang       
Department of Synthetic Materials and Functional Devices (SMFD), Max Planck Institute of Microstructure Physics, Max Planck Society;

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Fu,  Yubin       
Department of Synthetic Materials and Functional Devices (SMFD), Max Planck Institute of Microstructure Physics, Max Planck Society;

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Feng,  Xinliang       
Department of Synthetic Materials and Functional Devices (SMFD), Max Planck Institute of Microstructure Physics, Max Planck Society;

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Citation

Imran, M., Yang, L., Zhang, J.-J., Qiu, Z.-L., Fu, Y., Israel, N., et al. (2025). A persistent concealed non-Kekulé nanographene: synthesis and in situ characterization. Organic Chemistry Frontiers. doi:10.1039/D4QO02019G.


Cite as: https://hdl.handle.net/21.11116/0000-0010-7A36-9
Abstract
Concealed non-Kekulé (CNK) nanographenes have recently gained attention as promising non-Kekulé model systems due to their distinctive antiferromagnetic electronic spins, which offer potential applications in spintronics and quantum information science. However, synthesizing CNK nanographenes in solution remains a significant challenge because of their strong biradical character and high reactivity. In this study, we report the successful synthesis of a novel CNK nanographene with two phenalene units fused in a cis configuration to perylene (c-CNK), which exhibits persistent stability under ambient conditions, with a half-life (t1/2) of 59 minutes. The formation of c-CNK is confirmed using in situ UV-Vis-NIR spectroscopy, Raman spectroscopy, and high-resolution mass spectrometry. The open-shell character of c-CNK is supported by electron paramagnetic resonance (EPR) spectroscopy by observing an isotropic signal with a g-value of 2.0026. Quantum chemical simulations reveal a high biradical character (y0 = 0.97) and a singlet open-shell ground state with a small singlet–triplet energy gap (ΔES–T) of 0.4 kcal mol−1. This work presents a solution synthesis of a next-generation concealed non-Kekulé nanographene with intrinsic antiferromagnetic electronic spins, highlighting its potential as a promising material for future quantum technologies.