Synthesis and structures of O-anthrylmethyl-substituted hexahomotrioxacalix[3]arenes

O-Alkylation of 7,15,23-tri-tert-butyl-25,26,27-trihydroxy-2,3,10,11,18,19-hexahomo-3,11,19-trioxacalix[3]arene (1H₃) with 9-chloromethylanthracene 5 was carried out under different reaction conditions. Variation of the number of anthrylmethyl group introduced at the phenolic rim of hexahomotrioxacalix[3]arene 1H₃ was achieved through selective O-alkylation using stoichiometric amounts of 9-chloromethylanthracene 5 in acetone to afford the mono-O-alkylated product 2H₂An, the di-O-alkylated product 3HAn₂ and the tri-O-alkylated product partial-cone-4An₃, respectively. Interestingly, by using an acetone/benzene (1:1 v/v) mixed solvent system, the cone-4An₃ was successfully synthesized. These results suggest that the solvent can also control the conformation of the O-alkylation products. The possible reaction routes of the cone-4An₃ and partial-cone-4An₃ are also discussed