Chem. J. Chinese Universities

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Synthesis of 3-Arylthiophenes with Luminescent Property via Suzuki Cross-coupling Reaction Catalyzed by Cyclopalladated Ferrocenylimine

ZHANG Jin-Li1, WU Yang-Jie1*, LI Jing-Ya1, DU Chen-Xia1, ZHENG Ju-Mei1, THOMAS C. W. Mak2, SONG Mao-Ping1   

    1. Henan Province Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Province Universities, Department of Chemistry, Zhengzhou University, Zhengzhou 450052, China;
    2. Department of Chemistry, The Chinese University of HongKong, Shatin, New Territories, Hong Kong SAR, China
  • Received:2007-04-15 Revised:1900-01-01 Online:2007-12-10 Published:2007-12-10
  • Contact: WU Yang-Jie

Abstract: Aryl-substituted thiophenes are important fine chemicals and can constitute ubiquitous fragments of the active semiconducting layer in organic field effect transistors(OFETs). Among the variety of useful methods for the synthesis of these kinds of compounds, palladium-catalyzed Suzuki cross-coupling reaction received more researchers’ attentions. Cyclopalladated ferrocenylimines catalyzed Suzuki cross-coupling reaction of aryl iodides, bromides with 3-thienylboronic acid was carried out in DMF at 80 ℃ in the presence of K3PO4 and without the protection of inert gas. This method has the advantage of low loadings both of catalyst and 3-thienylboronic acid, simple and easy handling procedure. By using this method the synthesis of 3-arylthiophenes could be readily achieved. The emission and excitation spectra of compounds 3b, 3c, 3d confirmed that 3-arylsubstituted thiophenes were a kind of potential organic LEDs materials.

Key words: Cyclopalladated ferrocenylimine, Suzuki reaction, 3-Thienylboronic acid, 3-Aryl thiophenes, Emission spectrum, Excitation spectrum

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