Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (08): 1526-1532.DOI: 10.6023/cjoc201203007 Previous Articles     Next Articles



陈秋燕, 麻玉雯, 王成云, 沈永嘉   

  1. 结构可控先进功能材料及其制备技术教育部重点实验室 华东理工大学精细化工研究所 上海 200237
  • 收稿日期:2012-03-23 修回日期:2012-04-11 发布日期:2012-04-26
  • 通讯作者: 王成云
  • 基金资助:

    国家自然科学基金(Nos. 20872035, 21076078)和高等学校博士学科点专项科研基金(No. 20070251018)资助项目.

Synthesis of 1,3,5-Tris[(4'-ethynylphenyl)ethynyl]benzene

Chen Qiuyan, Ma Yuwen, Wang Chengyun, Shen Yongjia   

  1. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237
  • Received:2012-03-23 Revised:2012-04-11 Published:2012-04-26
  • Supported by:

    Project supported by the Natural Science Foundation of China (Nos. 20872035, 21076078) and the Specialized Research Fund for the Doctoral Program of Higher Education (No. 20070251018).

Several synthetic routes were designed to prepare 1,3,5-tris[(4-ethynylphenyl)ethynyl]benzene. The synthetic routes and reaction conditions were contrasted and discussed, when multiple Sonogashira reactions were occurred between multifunctional alkyne-terminal compounds and aromatic bromine compounds, the different substitution degree compounds with similar polarity were obtained, and they were difficult to separate. Whereas the reactions between multifunctional alkyne-terminal compounds and aromatic iodine compounds can avoid this situation. 1,3,5-Tribromobenzene reacted with 3-methylbutynol to afford 1,3,5-tris(3'-hydroxy-3'-methyl-but-1'-ynyl)benzene, then 1,3,5-triethynylbenzene was obtained by the cleavage reaction of the compound in presence of potassium hydroxide and toluene. On the other hand, using 4-iodoaniline and trimethyl silyl acetylene as raw materials, 4-trimethylsiylethynyl iodobenzene was synthesized by diazo reaction and halogenation. Therefore, 1,3,5-tris[(4'-ethynylphenyl)ethynyl]benzene was prepared by the cleavage reaction of the 1,3,5- triethynylbenzene and 4-trimethylsiylethynyl iodobenzene. The structures of the target compound and intermediates were confirmed by 1H NMR, 13C NMR techniques and element analysis.

Key words: 1,3,5-tris[(4'-ethynylphenyl)ethynyl]benzene, dendrimer, Sonogashira reaction