Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (2): 394-402.DOI: 10.6023/cjoc201606040 Previous Articles     Next Articles



欧亚平a, 张静b, 庾江喜a, 朱小明a   

  1. a 衡阳师范学院化学与材料科学学院 功能金属有机材料湖南省普通高等学校重点建设实验室 衡阳 421008;
    b 华中师范大学化学学院 农药与化学生物学教育部重点实验室 武汉 430079
  • 收稿日期:2016-06-29 修回日期:2016-09-02 发布日期:2016-10-18
  • 通讯作者: 欧亚平
  • 基金资助:


Synthesis, Spectral Properties and Theoretical Studies of 1,4-Bis[2-(4-pyridyl)ethenyl]benzene Derivatives

Ou Yapinga, Zhang Jingb, Yu Jiangxia, Zhu Xiaominga   

  1. a Key Laboratory of Functional Organometallic Materials of Hunan Province College, College of Chemistry and Material Science, Hengyang Normal University;Hengyang 421008;
    b Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079
  • Received:2016-06-29 Revised:2016-09-02 Published:2016-10-18
  • Supported by:

    Project supported by the Opening Subjects of Key Laboratory of Functional Organometallic Materials of Hunan Province (No. GN15K05), and the Scientific Research Foundation of the Hengyang Normal University (No. 14B23).

Four asymmetric hydrogen-bond acceptors of 1,4-bis[2-(4-pyridyl)ethenyl]benzene derivatives with higher yields were synthesized through the classical Witting-Horner and Sonogashira cross-coupling reactions, and their structures and spectral properties were investigated. The series of compounds all have been characterized by NMR, MS and element analysis. Crystal structures indicated that the conformation of hydrogen-bond self-assemble may be change due to the hindrance effect from the arylacetyl group in o-position of benzene. UV-Vis spectra combined with time-dependent density functional theory (TDDFT) calculation results showed that target compounds all display a strong π→π* and ICT transition absorptions. Fluorescence spectrum indicated that gradual increasing of conjugate systems make their emission peak tend to a red shift, which is conducive to π-π accumulation. Above results will provide certain synthetic basis and theoretical foundation for subsequent studies about regioselectivity of hydrogen-bond self-assemble and cyclization reactions from light.

Key words: Asymmetric hydrogen-bond acceptor, 1,4-Bis[2-(4-pyridyl)ethenyl]benzene, Crystal structure, Spectral properties