Naphthalene Diimides Endcapped with Ethynylazulene: Molecular Design, Synthesis and Properties

doi:10.6023/cjoc201609029

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (3): 711-719.DOI: 10.6023/cjoc201609029 Previous Articles Next Articles

ARTICLE

薁乙炔封端的萘二酰亚胺小分子的设计合成与场效应性能研究

辛涵申^a, 葛从伍^a, 傅丽娜^a,b, 杨笑迪^c, 高希珂^a

a 中国科学院上海有机化学研究所中国科学院有机功能分子合成与组装化学重点实验室上海 200032;
b 华东理工大学材料科学与工程学院上海 200237;
c 复旦大学先进材料实验室上海 200433

收稿日期:2016-09-27 修回日期:2016-10-25 发布日期:2016-11-17
通讯作者: 高希珂,E-mail:gaoxk@mail.sioc.ac.cn E-mail:gaoxk@mail.sioc.ac.cn
基金资助:
国家自然科学基金（No.21522209）、战略性先导科技专项B类（No.XDB12010100）和上海市科委（No.16JC1400603）资助项目.

Naphthalene Diimides Endcapped with Ethynylazulene: Molecular Design, Synthesis and Properties

Xin Hanshen^a, Ge Congwu^a, Fu Lina^a,b, Yang Xiaodi^c, Gao Xike^a

a Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
b School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237;
c Laboratory of Advanced Materials, Fudan University, Shanghai 200433

Received:2016-09-27 Revised:2016-10-25 Published:2016-11-17
Contact: 10.6023/cjoc201609029 E-mail:gaoxk@mail.sioc.ac.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21522209), the "Strategic Priority Research Program" (No. XDB12010100) and the Shanghai Science and Technology Committee (No. 16JC1400603).

1. Naphthalene Diimides Endcapped with Ethynylazulene: Molecular Design, Synthesis and Properties.PDF(1901KB)

Abstract

Azulene is noteworthy for its deep blue color with a large dipole moment. Compared to other unsaturated aromatic hydrocarbons, azulenes show unique photophysical and electrical properties. Herein, two isomers of 1,4,5,8-naphthalene diimide (NDI) endcapped with ethynylazulene units (1 and 2) are presented, which are capped with five-membered and seven-membered rings of azulene moieties, respectively. It is interesting that these two compounds show remarkably different physicochemical properties, thermal stabilities and organic field-effect transistors (OFET) performance resulting from the different connections of an electron-rich five-membered ring and an electron-poor seven-membered ring. Density functional theory (DFT) calculations reveal that the lowest unoccupied molecular orbital (LUMO) energy of 2 (endcapped with 6-ethynylalzulene) is lower than that of 1 (endcapped with 2-ethynylalzulene), and 2 makes the electrons of LUMO more delocalized, which favor the overlap of LUMO between molecules, thus to obtain higher mobility for 2. OFETs based on thin films of these two isomers were fabricated with conventional spin-coated techniques. Under nitrogen atmosphere, 1 and 2 show n-type semiconducting properties with electron mobilities of up to 0.022 and 0.16 cm²·V^-1·s^-1, respectively, which is consistent with the DFT results.

Key words: azulene, naphthalene diimide, isomer, organic field-effect transistors, mobility

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Xin Hanshen, Ge Congwu, Fu Lina, Yang Xiaodi, Gao Xike. Naphthalene Diimides Endcapped with Ethynylazulene: Molecular Design, Synthesis and Properties[J]. Chin. J. Org. Chem., 2017, 37(3): 711-719.

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薁乙炔封端的萘二酰亚胺小分子的设计合成与场效应性能研究

Naphthalene Diimides Endcapped with Ethynylazulene: Molecular Design, Synthesis and Properties

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