Chemical Research in Chinese Universities ›› 2010, Vol. 26 ›› Issue (1): 38-45.

• Articles • Previous Articles     Next Articles

Syntheses, Crystal Structures and Complexing Properties of 1,3-Distal Calix[4]arene Schiff Bases

LI Liang, GU Wei-wei and YAN Chao-guo*   

  1. College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, P. R. China
  • Received:2009-02-14 Revised:2009-03-23 Online:2010-01-04 Published:2010-03-29
  • Contact: YAN Chao-guo. E-mail: cgyan@yzu.edu.cn
  • Supported by:

    Supported by the National Natural Science Foundation of China(No.20672091).

Abstract:

Novel 1,3-distal p-tert-butylcalix[4]arene Schiff bases were efficiently synthesized in three steps. At first p-tert-butylcalix[4]arene was reacted with N-2-hydroxyethylphthalimide catalyzed by TPP/DEAD or alkylated with ω-haloalkylphthalimide in the system of K2CO3/KI/CH3COCH3 to give 1,3-distal diphthalimidoalkyl calixarenes, which were in turn hydrazinolyzed to give diaminoalkyl calixarenes. Then with the aid of the condensation of active calixarene amines with salicylaldehyde, 2-hydroxy-1-naphthaldehyde or pyridine-2-carboxaldehyde, a series of 1,3-distal calixarene Schiff bases was prepared in satisfied yields. The single crystal structures and complexing  properties of these Schiff bases for transition metal ions were studied.

Key words: Calixarene; Schiff base; Crystal structure; Metal complex; UV spectroscopy