Co-Inclusion of cyclic ethers and chloroform by a macrocycle with benzophenone-3,3′,4,4′-tetracarboxylic diimide units

A macrocycle having benzophenone-3,3′,4,4′-tetracarboxylic diimide and adamantane units (1) was synthesized from benzophenone-3,3′,4,4′-tetracarboxylic dianhydride and 1,3-adamantanedimethanamine in 37% yield. The crystallization of 1 and 1,4-dioxane (a) in chloroform resulted in the formation of inclusion crystal (1a), and the stoichiometric ratio of 1, chloroform, and a was 1 : 2 : 1. The host molecules were arranged to afford network structures with one-dimensional channels in the crystalline state, in which two different guest molecules were jointly accommodated through CH⋯O and CH⋯Cl interactions. Inclusion crystals containing cyclic ethers (b–d) with the same stoichiometric ratio were obtained under identical conditions. In all of the inclusion crystals, the shape and conformation of 1 and their arrangements were similar to those of crystal 1a, and the molecular structures of the liquid guests were characterized.