Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (7): 1514-1519.DOI: 10.6023/cjoc201412031 Previous Articles     Next Articles



范平, 徐生明, 李巍巍, 陈辰, 祃艳强   

  1. 辽宁大学化学院 沈阳 110036
  • 收稿日期:2014-12-17 修回日期:2015-02-06 发布日期:2015-03-03
  • 通讯作者: 范平
  • 基金资助:

    辽宁省教育局科学研究基金(No. L2011007)和沈阳市科技局科技计划(No. F13-318-1-51)资助项目.

Synthesis and Properties of Novel Azocalix[4]arene Derivatives with Azo and Imino Groups as the Lower Margin Chelating Arm

Fan Ping, Xu Shengming, Li Weiwei, Chen Chen, Ma Yanqiang   

  1. Institute of Chemistry, Liaoning University, Shenyang 11003
  • Received:2014-12-17 Revised:2015-02-06 Published:2015-03-03
  • Supported by:

    Project supported by the Liaoning Provincial Department of Education Fund for Scientific Research (No. L2011007) and the Shenyang Science and Technology Bureau of Science and Technology Program (No. F13-318-1-51).

A serious of calix[4]arene derivatives containing azo and imino group in the lower rim were synthesized by substitution and condensation reactions from p-tert-butylcalix[4]arene. The structures of products were characterized by IR, 1H NMR, 13C NMR and elemental analysis. Their complexation behavior toward various metal ions was investigated by UV/vis spectroscopy. The results showed that 25,27-dihydroxy-26,28-bis{2-[2-(N-(4-phenylazo-1-naphthyl)iminomethyl)phenoxy]- ethoxy}-p-tert-butylcalix[4]arene (4c) could identify Al3+ and Sn2+, and 25,27-dihydroxy-26,28-bis{2-[2-(N-(4-(4- methylphenylazo)-1-naphthyl)iminomethyl)phenoxy]ethoxy}-p-tert-butylcalix[4]arene (4e) could identify Al3+ specifically. The stoichiometry of 4e to Al3+ in the complex was 1:1.

Key words: calyx[4]arene, azo group, imino group, UV/Vis spectroscopy