Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (11): 3916-3924.DOI: 10.6023/cjoc202005014 Previous Articles     Next Articles

Special Issue: 创刊四十周年专辑


彭培珍a,b, 李晶b, 侯斌b, 辛涵申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:2020-05-06 修回日期:2020-05-22 发布日期:2020-06-01
  • 通讯作者: 程探宇, 高希珂;
  • 基金资助:

Design, Synthesis and Properties of Indacenodithiophene Derivatives End-Capped with Azulene

Peng Peizhena,b, Li Jingb, Hou Binb, Xin Hanshenb, Cheng Tanyua, Gao Xikeb   

  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 Sciences, Shanghai 200032
  • Received:2020-05-06 Revised:2020-05-22 Published:2020-06-01
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21522209, 21790362), and the Science and Technology Commission of Shanghai Municipality (Nos. 19XD1424700, 18JC1410600).

Two isomers of azulene and indacenodithiophene (IDT)-based compounds 1 and 2 were designed and synthesized, according to the different connections of azulene unit with IDT through its electron-rich five-membered ring and the electron-deficient seven-membered ring, respectively. The UV-Vis spectra, electrochemical properties and proton-responsive properties of 1 and 2 were studied. Compounds 1 and 2 show obviously different physicochemical properties and device performance of organic field-effect transistors (OFET). Both compounds 1 and 2 have reversible proton response characteristics. The end absorption peaks of these two compounds are between 400 and 600 nm before protonation. With the addition of trifluoroacetic acid (TFA), the absorption peaks are red shifted to 550~850 nm. When they are protonated fully (TFA volume ratio is about 1%), they are red shifted about 200 and 177 nm, respectively. The color of compounds 1 and 2 in dichloromethane solution before protonation is red after the adequate protonation. It turned to blue and returned to its original color after the addition of triethylamine. OFET thin film devices of 1 and 2 showed an order of magnitude difference, with hole mobilities of 4.14×10-3 and 1.05×10-5 cm2·V-1·s-1, respectively. The different connections of IDT and azulene units through the electronic rich five-membered ring and the electronic deficient seven-membered ring of azulene greatly affect the materials’ device performance as well as their physicochemical properties, providing valuable insights for developing azulene-based novel organic functional molecules.

Key words: azulene, indacenodithiophene, isomer, organic field effect transistors