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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 11: 4400 - 4408

DOI: https://doi.org/10.6023/cjoc202105023

ARTICLES

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

  • Min Zhou ,
  • Jing Li ,
  • Jie Cheng ,
  • Congwu Ge ,
  • Tanyu Cheng ,
  • Xike Gao
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  • 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
* Corresponding authors. E-mail: ;
;

Received date: 2021-05-12

  Revised date: 2021-07-15

  Online published: 2021-08-19

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)

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Abstract

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

Cite this article

Min Zhou , Jing Li , Jie Cheng , Congwu Ge , Tanyu Cheng , Xike Gao . Synthesis and Field-Effect Characteristics of the Chiral Naphthalene Diimide Derivatives[J]. Chinese Journal of Organic Chemistry, 2021 , 41(11) : 4400 -4408 . DOI: 10.6023/cjoc202105023

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