Syntheses and Properties of Five-Ring Fused Azo- and Thio-Aromatic Compounds Containing Imide Substituent

doi:10.6023/A15120782

Acta Chim. Sinica ›› 2016, Vol. 74 ›› Issue (4): 335-339.DOI: 10.6023/A15120782 Previous Articles Next Articles

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含有酰亚胺结构单元的氮杂和硫杂稠五环分子的合成与性能研究

杨宁^a,b, 乔小兰^b, 房忍忍^b, 陶竞炜^b, 郝健^a, 李洪祥^b

a. 上海大学化学系上海 200444;
b. 中国科学院上海有机化学研究所上海 200032

投稿日期:2015-12-18 发布日期:2016-03-03
通讯作者: 郝健, 李洪祥 E-mail:jhao@shu.edu.cn;lhx@mail.sioc.ac.cn
基金资助:
项目受国家自然科学基金(Nos. 51273212, 51303201)资助.

Syntheses and Properties of Five-Ring Fused Azo- and Thio-Aromatic Compounds Containing Imide Substituent

Yang Ning^a,b, Qiao Xiaolan^b, Fang Renren^b, Tao Jingwei^b, Hao Jian^a, Li Hongxiang^b

a Department of Chemistry, Shanghai University, Shanghai 200444;
b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2015-12-18 Published:2016-03-03
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 51273212, 51303201).

Five-ring fused azo-and thio-aromatic compounds 1 and 2 containing imide substituent were designed and synthesized. 3,4-Dibromo-1-(2-ethylhexyl)-1H-pyrrole-2,5-dione reacted with lithium indyl and benzothiophene-3-boronic acid respectively, affording intermediates 3 and 4. Compound 3 was intramolecular cyclized in the presence of PdCl₂ to give target compound 1. And compound 2 was prepared through intramolecular cyclization of intermediate 4 by means of photochemical ringclosure reaction and oxidation. The physicochemical properties of compounds 1 and 2 were thoroughly investigated with TGA, UV-vis absorption spectra and cyclic voltammetry. Experimental results showed the introduction of imide substituent not only increased the solubility of compounds 1 and 2, but also decreased their energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO). The HOMO/LUMO energy levels of compounds 1 and 2 are -5.58/-2.25 eV and -6.04/-3.51 eV respectively. Single crystals of compound 1 were grown through solvent evaporation method in the mixture of dichloromethane and petroleum ether. Single crystal structure revealed compound 1 has a planar conjugated core and forms dimmer in the crystal. Strong π-π intermolecular interactions exist in the dimmer, and hydrogen bonds (NH…O＝C) are observed among dimmers. The charge carrier mobilities of compounds 1 and 2 were investigated through thin film transistors. The transistors were fabricated with top-contact/bottom-gate device configurations. And thin films were deposited in vacuum on octadecyltrichlorosilane (OTS)-modified Si/SiO₂ substrates. Transistors performance of compound 2 displays obvious p-type performance with a mobility of 2.75×10^-3 cm²·V^-¹·s^-¹. However, compound 1 exhibited no organic field-effect transistor (OFET) behavior. In order to understand the different device performances of compounds 1 and 2, their thin films were investigated by atomic force microscopy (AFM) and X-ray diffraction (XRD). AFM images showed that compound 1 formed continuous thin film with small size of microstructures, the existence of grain boundaries hindered the transport of charge carriers in the film. XRD curves revealed that compound 2 formed crystalline thin films. Though the continuity of 2 films was worse than that of 1, the larger size of microstructures and the crystalline property of the films facilitated the transport of charge carriers.

Key words: organic semiconductors, five-ring fused aromatic molecules, organic thin film transistors

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Yang Ning, Qiao Xiaolan, Fang Renren, Tao Jingwei, Hao Jian, Li Hongxiang. Syntheses and Properties of Five-Ring Fused Azo- and Thio-Aromatic Compounds Containing Imide Substituent[J]. Acta Chim. Sinica, 2016, 74(4): 335-339.

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含有酰亚胺结构单元的氮杂和硫杂稠五环分子的合成与性能研究

Syntheses and Properties of Five-Ring Fused Azo- and Thio-Aromatic Compounds Containing Imide Substituent

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