Citation: Tingting Huang, Zhuanlong Ding, Hao Liu, Ping-An Chen, Longfeng Zhao, Yuanyuan Hu, Yifan Yao, Kun Yang, Zebing Zeng. Electron-transporting boron-doped polycyclic aromatic hydrocarbons: Facile synthesis and heteroatom doping positions-modulated optoelectronic properties[J]. Chinese Chemical Letters, ;2024, 35(4): 109117. doi: 10.1016/j.cclet.2023.109117 shu

Electron-transporting boron-doped polycyclic aromatic hydrocarbons: Facile synthesis and heteroatom doping positions-modulated optoelectronic properties

Tingting Huang ^{a, b} ,
Zhuanlong Ding ^{a, b} ,
Hao Liu ^a ,
Ping-An Chen ^c ,
Longfeng Zhao ^c ,
Yuanyuan Hu ^c ,
Yifan Yao ^a ,
Kun Yang ^{a, b, *,} ,
Zebing Zeng ^{a, b, *,}

a.
Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
b.
Shenzhen Research Institute of Hunan University, Shenzhen 518000, China
c.
Key Laboratory for Micro/Nano Optoelectronic Devices of Ministry of Education and Hunan Provincial Key Laboratory of Low-Dimensional Structural Physics and Devices School of Physics and Electronics, Hunan University, Changsha 410082, China

yangk@hnu.edu.cn

zbzeng@hnu.edu.cn

Received Date: 4 July 2023
Revised Date: 13 September 2023
Accepted Date: 17 September 2023
Available Online: 22 September 2023

Figures(6)

While heteroatom doping serves as a powerful strategy for devising novel polycyclic aromatic hydrocarbons (PAHs), the further fine-tuning of optoelectronic properties via the precisely altering of doping patterns remains a challenge. Herein, by changing the doping positions of heteroatoms in a diindenopyrene skeleton, we report two isomeric boron, sulfur-embedded PAHs, named Anti-B₂S₂ and Syn-B₂S₂, as electron transporting semiconductors. Detailed structure-property relationship studies revealed that the varied heteroatom positions not only change their physicochemical properties, but also largely affect their solid-state packing modes and Lewis base-triggered photophysical responses. With their low-lying frontier molecular orbital levels, n-type characteristics with electron mobilities up to 1.5 × 10⁻³ cm² V⁻¹ s⁻¹ were achieved in solution-processed organic field-effect transistors. Our work revealed the critical role of controlling heteroatom doping patterns for designing advanced PAHs.
- Polycyclic aromatic hydrocarbon,
- Optoelectronic properties,
- Heteroatom doping,
- n-Type organic semiconductors,
- Structure–property relationship
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