The regioselective syntheses of novel p-tert-butylcalix[4]arenes with functional aldehyde and dithiocar-bazate Schiff base groups were carried out.p-tert-Butylcalix[4]arene was alkylated with o-,H-(ω-chloroalkoxy)-benzaldehydes in the system of K;CO;/KI/CH;CN to give calixarene 1,3-dialdehydes.Then the condensation reactions of active calixarene aldehydes with S-methyl and S-benzyldithiocarbazate,calixarene sulfur-containing Schiff bases were efficiently obtained in satisfied yields.The single crystal analysis of the four representative products shows that calixarene aldehydes and Schiff bases exist in cone conformation and there are interesting intermolecular hydrogen-bands andπ…πinteraction in the crystals.