Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (03): 551-557.DOI: 10.6023/cjoc201211031 Previous Articles     Next Articles



许晨, 黄鹏程   

  1. 北京航空航天大学材料科学与工程学院 北京 100191
  • 收稿日期:2012-11-15 修回日期:2012-12-14 发布日期:2012-12-18
  • 通讯作者: 黄鹏程

Synthesis of Novel Phenylacetylene Dendrimers Containing Different Protective Groups for Their Terminal Acetylenes

Xu Chen, Huang Pengcheng   

  1. College of Material Science and Technology, Beihang University, Beijing 100191
  • Received:2012-11-15 Revised:2012-12-14 Published:2012-12-18

Using Sonogashira coupling reaction, two kinds of 1,3,5-substituted phenylacetylene dendrimers: 1,3,5-tris[3-(3- hydroxy-3-methyl-1-butynyl)-5-(triisopropylsilylethynyl)phenylethynyl]benzene (B1) and 1,3,5-tris[3-(trimethylsilylethynyl)- 5-(triisopropylsilylethynyl)phenylethynyl]benzene (B2) were synthetized and the synthetic routes were compared and discussed. The structures of the target compounds and intermediates were confirmed by 1H NMR, 13C NMR, EI-MS, HRMS techniques and element analysis. In phenylacetylene dendrimers B1 and B2, the six terminal acetylene groups on their periphery were protected by two different kinds of groups, respectively. Based on the different deprotection conditions, two different kinds of functional groups could be introduced to B1 and B2, respectively.

Key words: phenylacetylene dendrimer, Sonogashira reaction, 1,3,5-tris[3-(3-hydroxy-3-methyl-1-butynyl)-5-(triisopropyl- silylethynyl)phenylethynyl]benzene, 1,3,5-tris[3-(trimethylsilylethynyl)-5-(triisopropylsilylethynyl)phenylethynyl]benzene