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



辛涵申a, 葛从伍a, 傅丽娜a,b, 杨笑迪c, 高希珂a   

  1. 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,
  • 基金资助:


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

Xin Hanshena, Ge Congwua, Fu Linaa,b, Yang Xiaodic, Gao Xikea   

  1. 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
  • 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).

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