Citation: Kexiang Zhao, Zongrui Wang, Qi-Yuan Wan, Jing-Cai Zeng, Li Ding, Jie-Yu Wang, Jian Pei. Janus-type BN-embedded perylene diimides via a "shuffling" strategy: Regioselective functionalizable building block towards high-performance n-type organic semiconductors[J]. Chinese Chemical Letters, ;2025, 36(6): 110339. doi: 10.1016/j.cclet.2024.110339 shu

Janus-type BN-embedded perylene diimides via a "shuffling" strategy: Regioselective functionalizable building block towards high-performance n-type organic semiconductors

Kexiang Zhao ^a ,
Zongrui Wang ^b ,
Qi-Yuan Wan ^a ,
Jing-Cai Zeng ^a ,
Li Ding ^a ,
Jie-Yu Wang ^{a, *,} ,
Jian Pei ^a

a.
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Center of Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
b.
Center for Soft Matter Science and Engineering, State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, China

jieyuwang@pku.edu.cn

Received Date: 27 April 2024
Revised Date: 3 August 2024
Accepted Date: 13 August 2024
Available Online: 13 August 2024

Figures(6)

Regioselevtive functionalization of perylene diimides (PDIs) at bay area often requires multistep synthesis and strenuous recrystallization. Direct bromination of perylene diimides only afford the 1, 6 and 1, 7-regioisomers. More importantly, the 1, 6-dibromo regioisomers could only be separated by preparative HPLC. Herein, we report a promising strategy for constructing Janus backbone of BN-doped perylene diimide derivatives. This Janus-type configuration results in the unique regioselective functionalization of BN-JPDIs, which yields exclusively the 1, 6-regioisomers. Further investigation shows that the Janus-type configuration leads to a net dipole moment of 1.94 D and intramolecular charge transfer, which causes substantial changes on the optoelectronic properties. Moreover, the single crystal organic field-effect transistors based on BN-JPDIs exhibit electron mobilities up to 0.57 cm² V⁻¹ s⁻¹, showcasing their potential as versatile building block towards high-performance n-type organic semiconductors.
- BN heterocycles,
- Perylene diimides,
- Regioselective functionalization,
- Intramolecular charge transfer,
- N-type organic semiconductors
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