Citation: Fangwei Ding, Debin Xia, Xiping Ding, Ruibin Deng, Congwu Ge, Yulin Yang, Ruiqing Fan, Kaifeng Lin, Xike Gao. Benzothiophene and benzosulfone fused pyrazino[2,3-g]quinoxaline: Synthesis and semiconducting properties[J]. Chinese Chemical Letters, ;2023, 34(2): 107235. doi: 10.1016/j.cclet.2022.02.040 shu

Benzothiophene and benzosulfone fused pyrazino[2,3-g]quinoxaline: Synthesis and semiconducting properties

Fangwei Ding ^a ,
Debin Xia ^{a, *,} ,
Xiping Ding ^a ,
Ruibin Deng ^a ,
Congwu Ge ^b ,
Yulin Yang ^a ,
Ruiqing Fan ^a ,
Kaifeng Lin ^{a, *,} ,
Xike Gao ^{b, *,}

a.
MIIT Key Laboratory of Critical Materials Technology for New Energy Conversion and Storage, School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China
b.
Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, Shanghai 200032, China

xia@hit.edu.cn

linkaifeng@hit.edu.cn

gaoxk@mail.sioc.ac.cn

Received Date: 4 November 2021
Revised Date: 26 November 2021
Accepted Date: 15 February 2022
Available Online: 19 February 2022

Figures(6)

A novel air-stable n-type benzothiaphene endcapped azaarene (BTPQ) and its sulfonated derivative (BSPQ) were prepared via two pathways and characterized by NMR, UV–vis, fluorescence and cyclic voltammetry spectroscopy. Symmetrically introducing four nitrogen atoms into acenes, the semiconductor properties could be changed from p-type to n-type detected through the space charge limited current (SCLC) method. After sulfonation of BTPQ, BSPQ is with deeper frontier orbital energy levels and enhanced the electron mobility.
- Azaarenes,
- Deep LUMO levels,
- n-type,
- Organic semiconductor,
- Polycyclic aromatic hydrocarbons
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