Citation: Li Jing, Hu Yong-Hui, Ge Cong-Wu, Gong He-Gui, Gao Xi-Ke. The role of halogen bonding in improving OFET performance of a naphthalenediimide derivative[J]. Chinese Chemical Letters, ;2018, 29(3): 423-428. doi: 10.1016/j.cclet.2017.06.008 shu

The role of halogen bonding in improving OFET performance of a naphthalenediimide derivative

Li Jing ^a,b ,
Hu Yong-Hui ^b ,
Ge Cong-Wu ^b,, ,
Gong He-Gui ^a,, ,
Gao Xi-Ke ^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

Corresponding author: Ge Cong-Wu, gecongwu@sioc.ac.cn Gong He-Gui, hegui_gong@shu.edu.cn Gao Xi-Ke, gaoxk@mail.sioc.ac.cn
Received Date: 28 April 2017
Revised Date: 19 May 2017
Accepted Date: 2 June 2017
Available Online: 7 March 2017

Figures(6)

Controlling microstructure and thin film morphology of organic semiconductors by supramolecular arrangement is critical to improving their device performance. To realize well-controlling supramolecular assembly, a core-expanded naphthalene diimides derivative (1) was designed and synthesized as an n-type organic semiconductor and also as a halogen bonding (XB) donor that could form complementary XBs with 2, 2-dipyridine or 2, 2-bipyrimidine acceptor. The XB interactions in the solid state of 1/2, 2-dipyridine and 1/2, 2-bipyrimidine were confirmed by a series of characterization methods, such as thermal gravimetric analysis (TGA), X-ray photoelectron spectroscopy (XPS), nuclear magnetic resonance (NMR) involving ¹⁹F NMR and solid-state ¹³C NMR. Organic field-effect transistors (OFETs) based on XB complexes 1/2, 2-dipyridine or 1/2, 2-bipyrimidine showed better device performance than that of devices based on pure 1, with the average electron mobility increased more than doubled (from 0.027 cm² V^-1 s^-1 to 0.070 cm² V^-1 s^-1).
- Supramolecular assembly,
- Halogen bond,
- Naphthalene diimide,
- Organic semiconductor,
- Organic field-effect transistor
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