Citation: Youxiang He, Yongfa Zhu, Ming Luo, Haiping Xia. A nonalternant analogue of pentacene incorporating a non-terminal azulene unit[J]. Chinese Chemical Letters, ;2025, 36(7): 110463. doi: 10.1016/j.cclet.2024.110463 shu

A nonalternant analogue of pentacene incorporating a non-terminal azulene unit

Youxiang He ^a ,
Yongfa Zhu ^a ,
Ming Luo ^{b, *,} ,
Haiping Xia ^{a, b, *,}

a.
Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China
b.
Shenzhen Grubbs Institute and Guangdong Provincial Key Laboratory of Catalysis, Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China

luom3@sustech.edu.cn

xiahp@sustech.edu.cn

Received Date: 18 July 2024
Revised Date: 30 August 2024
Accepted Date: 13 September 2024
Available Online: 14 September 2024

Figures(6)

Azulene-fused acenes demonstrate enhanced stability, unique aromaticity, and distinctive photophysical properties, rendering them significant in organic electronics. In the present study, we report a new type of nonalternant analogue of pentacene incorporating a non-terminal azulene unit. Aromaticity analyses reveal that the five-membered rings in this analogue exhibit antiaromatic. The extensive conjugated aryl substituents on the acene's side shift the HOMO distributions from the naphthyl ring and metallacycle to the aryl groups, thereby narrowing the HOMO–LUMO energy gap and enhancing absorptions in the low-energy regions. Furthermore, these fused acenes readily react with base rather than acid, resulting in reversible base/acid stimuli responsiveness.
- Azulene,
- Aromaticity,
- DFT calculations,
- Reversible stimuli responsiveness,
- Photophysical properties
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