Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (9): 2919-2928.DOI: 10.6023/cjoc202005035 Previous Articles     Next Articles


谭丹a, 吴赛a, 魏欢b, 胡袁源b, 陈华杰a   

  1. a 湘潭大学化学学院 环境友好化学与应用教育部重点实验室 湖南湘潭 411105;
    b 湖南大学物理与微电子科学学院 微纳光电器件及应用教育部重点实验室 长沙 410082
  • 收稿日期:2020-05-14 修回日期:2020-06-12 发布日期:2020-06-28
  • 通讯作者: 陈华杰,
  • 基金资助:

Design, Synthesis, and Properties of Conjuated Molecules with Isatin-Fused Acenaphthenequinone Imide Moieties

Tan Dana, Wu Saia, Wei Huanb, Hu Yuanyuanb, Chen Huajiea   

  1. a Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, Hunan 411105;
    b Key Laboratory for Micro/Nano Optoelectronic Devices of Ministry of Education, School of Physics and Electronics, Hunan University, Changsha 410082
  • Received:2020-05-14 Revised:2020-06-12 Published:2020-06-28
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21875202), the Hunan Provincial Natural Science Foundation of China (No. 2018JJ1024), and the Science and Technology Planning Project of Hunan Province (No. 2017RS3048).

Two highly electron-deficient, novel isoindigo (IID) derivative acceptor units, including isatin-fused acenaphthenequinone imide (A1) and nitrogen-doped isatin-fused acenaphthenequinone imide (A2), were designed and synthesized via Knoevenagel consendation reaction. In comparison with the well-known IID unit, both A1 and A2 acceptor units exhibit reduced LUMO energy levels (ca. -4.0 eV) and extended π-conjugation backbone owing to the incorporation of strongly electron-withdrawing acenaphthenequinone imide. The properties observed here for both A1 and A2 are thus indicative of promising potential in the development of n-type organic semiconductors. On the basis of both A1 and A2 acceptor units, two A-A type organic π-conjugated molecules (BA1 and BA2) were further designed and synthesized by self-coupling of two identical A1 or A2 acceptor units. The effect of pyridal nitrogen on the backbone structure, optical absorption, energy level, and carrier mobility of the as-prepared π-conjugated molecules is studied systematically. The comparative investigation reveals that self-coupling of dual acceptor units into BA1 and BA2 not only endows them with extended conjugation backbone and enhanced molecular symmetry, but also improves their light-capturing abilities in the whole ultraviolet-visible region as relative to their parent acceptor units (A1 and A2). Moreover, the pyridal N-containing BA1 and BA2 possess enhanced backbone coplanarity and electron affinity as compared to their parent units (A1 and A2), thereby leading to reduced HOMO and LUMO energy levels. Finally, n-type thin-film transistors are further fabricated by adopting both BA1 and BA2 as the active layers, affording the electron motilities of 1.64×10-3 and 2.52×10-3 cm2·V-1·s-1, respectively.

Key words: isatin, acenaphthenequinone imide, isoindigo, electron mobility