Synthesis, Crystal Structure and Complexing Properties of Calix[4]arene Schiff Bases

Four p-tert-butylcalix[4]arene derivatives with different Schiff base groups at the lower rim were efficiently prepared in three steps. p-tert-Butylcalix[4]arene was firstly O-peralkylated with ω-haloalkylphthalimide in the system of NaH/DMF to give calixarene tetraalkylphthalimides, which were in turn hydrazinolyzed to give tetraaminoalkylcalixarenes. Then by condensation of the latter with salicylaldehyde and 2-hydroxy-1-naphthaldehyde, a series of calixarene Schiff bases were obtained in satisfying yields. The complexing properties of these Schiff bases for transition metal ions were investigated with UV spectroscopy.

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