Structure analysis of inclusion crystals of diimide-based macrocycles with halocarbons

Abstract

Three diimide-based macrocycles containing adamantane units were employed as hosts for the creation of inclusion crystals containing several liquid halocarbons. Crystals 1a with iodomethane and 1b with 1,2-dibromoethane were produced by using macrocycle 1 possessing pyromellitic diimide moieties. In crystal 1a, reactive iodomethane was encapsulated within the cavity of 1, where C–I⋯π contacts between the iodine atoms and the pyromellitic diimide units were observed. Crystal 2a with bromoform or 3a with chloroform was formed by using macrocycles possessing naphthalenediimide parts (2) or oxydiphthalimide units (3), respectively. The trihalomethanes were captured in the cavities of the macrocycles through C–X⋯π contacts in addition to other non-covalent interactions.