Abstract
Adamantane derivatives represent valuable scaffolds for the generation of interesting supramolecular architectures in the crystalline state because of their high symmetry and the facile attachment of functional groups. Tri- and tetrasubstituted adamantanes with dimethoxyphenol moieties were designed and prepared as novel hydrogen-bonded (H-bonded) electron-donor molecules with the aim of introducing donor–acceptor interactions into the H-bonded structures. Single-crystal X-ray analysis of ternary molecules based on adamantane (1) revealed the creation of one-dimensional (1D) ladders through H-bonding between methoxy and hydroxyl groups of dimethoxyphenol units. Individual ladders assembled into three-dimensional (3D) networks via multiple C–H⋯O interactions. In the crystals of tetrasubstituted adamantane (2), H-bonded 1D polymers composed of a cyclic framework were produced, which were aligned into a 3D network structure through C–H⋯O interactions. In the 1,3,5-trinitrobenzene (3) charge-transfer complex of trisubstituted adamantane, infinite H-bonded two-dimensional (2D) sheets were sustained by the formation of multiple H-bonds. The 2D sheets were observed to stack with guest molecules via charge-transfer interactions. The complexation of 3 with 2 led to the formation of H-bonded 2D sheets possessing two types of cavities, which were intermolecularly interdigitated via donor–acceptor interactions, resulting in the construction of a 3D network structure.
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