Citation: Liang Long, Liu Li-Na, Chen Xue-Qiang, Xiang Xuan, Ling Jun, Lu Zheng-Quan, Li Jing-Jing, Li Wei-Shi. Benzodithiophene/Benzothiadiazole-Based ADA-Type Optoelectronic Molecules: Influence of Fluorine Substitution[J]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 157-169. doi: 10.6023/cjoc201808034 shu

Benzodithiophene/Benzothiadiazole-Based ADA-Type Optoelectronic Molecules: Influence of Fluorine Substitution

Liang Long ^a,b,† ,
Liu Li-Na ^b,† ,
Chen Xue-Qiang ^b ,
Xiang Xuan ^b ,
Ling Jun ^c ,
Lu Zheng-Quan ^a ,
Li Jing-Jing ^a ,
Li Wei-Shi ^a,b,,

a.
Zhengzhou Engineering Research Center for High Performance Organic Functional Materials, Zhengzhou Institute of Technology, Zhengzhou 450044
b.
Key Laboratory of Synthetic and Self-assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
c.
Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 320027

Corresponding author: Li Wei-Shi, liws@mail.sioc.ac.cn

^†

Received Date: 28 August 2018
Revised Date: 25 October 2018
Available Online: 11 January 2018
Fund Project: the Strategic Priority Research Program of Chinese Academy of Sciences XDB20020000the Science and Technology Open Cooperation Projects of Henan Province 162106000018Project supported by the National Natural Science Foundation of China (Nos. 21474129, 21674125, 51761145043), the Strategic Priority Research Program of Chinese Academy of Sciences (No. XDB20020000), the Science and Technology Open Cooperation Projects of Henan Province (Nos. 162106000018, 172106000067) and the Zhengzhou Institute of Technologythe National Natural Science Foundation of China 21674125the Science and Technology Open Cooperation Projects of Henan Province 172106000067the National Natural Science Foundation of China 21474129the National Natural Science Foundation of China 51761145043

Figures(11)

Fluorination on conjugated components is one of popular strategies to modify organic optoelectronic materials. Following the research of a benzodithiophene/benzothiadiazole ADA-type optoelectronic molecule, two benzothiadiazole (BT) units were fluorinated with different numbers and positions, and the change in basic properties and performances for field-effect transistors and organic solar cells was investigated. It was found that when the F-substitution number increases, the molecule enhances thermal stability, decreases solubility, lowers HOMO and LUMO energy levels, but almost does not alter light absorption range. Furthermore, investigations on organic field-effect transistors found the molecular hole mobility reduces with only one F-substituent at outer position of BT units, while increases up to 0.27 cm²·V^-1·s^-1 with two F substituents on BT units. However, when these materials are applied in organic solar cells, the fluorinated ones enhance open-circuit voltage, but deteriorate active layer morphology, finally leading to decrease in short-circuit current and device efficiency.
- organic optoelectronic materials,
- fluorination effect,
- organic field-effect transistors,
- organic solar cells
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