Citation: Dong Lu, Xiao-Chun Yang, Bing Leng, Xiao-Di Yang, Cong-Wu Ge, Xue-Shun Jia, Xi-Ke Gao. Fine-tuning the molecular energy levels by incorporating thiophene units onto the π-backbone of core-expanded naphthalene diimides[J]. Chinese Chemical Letters, ;2016, 27(7): 1022-1026. doi: 10.1016/j.cclet.2016.05.003 shu

Fine-tuning the molecular energy levels by incorporating thiophene units onto the π-backbone of core-expanded naphthalene diimides

Dong Lu ^a,b ,
Xiao-Chun Yang ^b ,
Bing Leng ^b ,
Xiao-Di Yang ^c ,
Cong-Wu Ge ^b,, ,
Xue-Shun Jia ^a,, ,
Xi-Ke Gao ^b,,

a.
Department of Chemistry, College of Science, Shanghai University, Shanghai, 200444, 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
c.
Laboratory of Advanced Materials, Fudan University, Shanghai, 200433, China

Corresponding author: Cong-Wu Ge, gecongwu@sioc.ac.cn Xue-Shun Jia, xsjia@mail.shu.edu.cn Xi-Ke Gao, gaoxk@mail.sioc.ac.cn
Received Date: 29 March 2016
Revised Date: 18 April 2016
Accepted Date: 22 April 2016
Available Online: 1 July 2016

Figures(5)

A series of core-expanded naphthalene diimides (NDI-DTYM) and thiophene-based derivatives (1a-c) were designed and synthesized to investigate the relationship between molecular structures and the highest occupied molecular orbital (HOMO) energy levels but has little impact on the lowest unoccupied molecular orbital (LUMO) energy levels. The results demonstrated that increasing the number of thiophene units can gradually elevate the HOMO energy levels but had little impact on the LUMO energy levels. The n-channel organic field-effect transistors (OFETs) based on 1b and 1c have demonstrated that these almost unchanged LUMO energy levels are proper to transport electrons.
- Naphthalene diimide,
- Thiophene,
- Molecular energy level,
- Organic transistor,
- Organic semiconductor
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