A stable open-shell peri-hexacene with remarkable diradical character

Jinji Zhang, Xiaojing Fang, Weiwei Niu, Yiming Yu, Yanlin Hu, Jiawen Sun, Ying Xu, Zhihua Zhou, Heyuan Liu, Xiaonan Fan, Baishu Zheng (), Qing Jiang (), Guangwu Li () and Wangdong Zeng ()
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Jinji Zhang: Hunan University of Science and Technology
Xiaojing Fang: Hunan University of Science and Technology
Weiwei Niu: Nankai University
Yiming Yu: Hunan University of Science and Technology
Yanlin Hu: Hunan University of Science and Technology
Jiawen Sun: Hunan University of Science and Technology
Ying Xu: Hunan University of Science and Technology
Zhihua Zhou: Hunan University of Science and Technology
Heyuan Liu: China University of Petroleum (East China)
Xiaonan Fan: China University of Petroleum (East China)
Baishu Zheng: Hunan University of Science and Technology
Qing Jiang: Hunan University of Science and Engineering
Guangwu Li: Nankai University
Wangdong Zeng: Hunan University of Science and Technology

Nature Communications, 2025, vol. 16, issue 1, 1-9

Abstract: Abstract [n]Peri-acenes ([n]PA) have attracted great interest as promising candidates for nanoelectronics and spintronics. However, the synthesis of large [n]PA (n > 4) is extremely challenging due to their intrinsic open-shell radical character and high reactivity. Herein, we report the successful synthesis and isolation of a derivative (1) of peri-hexacene in crystalline form. The structure of 1 is unequivocally confirmed by X-ray crystallographic analysis. Its ground state, aromaticity and photophysical properties are systematically studied by both experimental methods and theoretical calculations. Although the parent peri-hexacene is calculated to have a very large diradical character (y0 = 94.5%), 1 shows reasonable stability (t1/2 = 24 h under ambient conditions) due to the kinetic blocking. 1 exhibits an open-shell singlet ground state with a small singlet-triplet energy gap (−1.33 kcal/mol from SQUID measurements). 1 has also a narrow HOMO-LUMO energy gap (1.05 eV) and displays amphoteric redox behavior. This work opens new avenues for the design and synthesis of stable zigzag-edged graphene-like molecules with significant diradical character.

Date: 2025
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DOI: 10.1038/s41467-024-55556-5

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