Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4400-4408.DOI: 10.6023/cjoc202105023 Previous Articles     Next Articles

ARTICLES

萘二酰亚胺手性衍生物的合成及其场效应晶体管性能研究

周敏a,b, 李晶b, 程杰b, 葛从伍b,*(), 程探宇a,*(), 高希珂b,*()   

  1. a 上海师范大学化学与材料科学学院 上海 200234
    b 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
  • 收稿日期:2021-05-12 修回日期:2021-07-15 发布日期:2021-08-17
  • 通讯作者: 葛从伍, 程探宇, 高希珂
  • 基金资助:
    国家自然科学基金(21522209); 国家自然科学基金(21790362); 上海市科学技术委员会(19XD1424700); 上海市科学技术委员会(18JC1410600)

Synthesis and Field-Effect Characteristics of the Chiral Naphthalene Diimide Derivatives

Min Zhoua,b, Jing Lib, Jie Chengb, Congwu Geb(), Tanyu Chenga(), Xike Gaob()   

  1. a College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200234
    b Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032
  • Received:2021-05-12 Revised:2021-07-15 Published:2021-08-17
  • Contact: Congwu Ge, Tanyu Cheng, Xike Gao
  • Supported by:
    National Natural Science Foundation of China(21522209); National Natural Science Foundation of China(21790362); Science and Technology Commission of Shanghai Municipality(19XD1424700); Science and Technology Commission of Shanghai Municipality(18JC1410600)

Naphthalene diimides (NDI)-based conjugated molecules were a class of typical and widely studied organic semiconducting materials. The optically pure compounds (I-R and I-S) and mesomer (I-R,S) by SNAr reactions between tetraboromo-NDI and 1,2-diaminocyclohexane were designed and synthesized, moreover, the racemic mixture (I-rac) was obtained by mixing I-R and I-S equimolarly. The UV-vis absorption spectroscopy, cyclic voltammetry, and circular dichroism of four materials were studied. The UV-Vis absorptions in solution were consistent, while the absorptions in film were slightly different between the optically pure compounds and the mesomer or raceme, indicating the different aggregate structures. Accordingly, the organic field-effect transistors (OFET) by using these materials as the active layer were prepared. They all exhibited p-type organic semiconducting characteristics under nitrogen conditions. Meanwhile, mesomer (I-R,S) and raceme (I-rac) showed better OFET device performance (hole mobility: about 0.075 cm2•V–1•s–1) than that of the optically pure compounds I-R and I-S (hole mobility: about 0.04 cm2•V–1•s–1). The atomic force microscopy (AFM) studies demonstrated that thin films of mesomer (I-R,S) and raceme (I-rac) annealed at 100 ℃ showed larger form size of microstructures with fewer grain boundaries, which was consistent with the enhanced device performance after thermal annealing. This paper proved that the chirality influenced the molecule self-assembly, packing structure and the resulting device performance.

Key words: naphthalene diimides, chirality, aggregate structure, organic field-effect transistors