Co-crystals built from macrocycles with pyromellitic diimides and naphthalene derivatives: transformation of a binary co-crystal solvate to a solvate through solvent exchange†

The design and exploitation of co-crystals containing macrocyclic compounds has captivated researchers in various fields owing to their potential and practical applications. The crystallization of an adamantane-bearing macrocycle having pyromellitic diimide units (1) with 2,6-dibromonaphthalene-1,5-diol (2) and 1,5-dihydroxynaphthalene (3) afforded hydrogen-bonded charge-transfer co-crystals with solvent molecules. Co-crystals composed of 1 and 3 had 1D pores. Soaking the co-crystals of 1 and 3 in diethyl ether resulted in the release of 3 from the co-crystals and the formation of crystals composed of only 1, which captured diethyl ether through solvent exchange. These observations demonstrate a transformation from a binary co-crystal solvate to a solvate.