![]() In the CT-B superstructure, the CHCl 3 lattice molecules establish more » a set of and intermolecular interactions, leading to the formation of a hexagonal grid of solvent in which NDI-Δ forms a triangular grid. Confinement of TTF inside the NDI-Δ cavities in the CT-A superstructure enhances the CT character with the observation of a broad absorption band in the NIR region. Here, solvent modulation plays a critical role in controlling not only the NDI-Δ:TTF stoichiometric ratios and the molecular arrangements in the crystal superstructures, but also prevents the inclusion of TTF guests inside the cavities of NDI-Δ. Using MeCN, CHCl 3, and CH 2Cl 2, we identified three sets of cocrystals, namely CT-A, CT-B, and CT-C, respectively. Different solvents lead to different packing arrangements. Cocrystallization of NDI-Δ with tetrathiafulvalene (TTF) leads systematically to the formation of 2D tessellations as a result of superstructure-directing CT interactions. Utilization of nonhalogenated solvents, combined with careful tailoring of the concentrations, results in NDI-Δ self-assembling though interactions into 2D honeycomb triangular and hexagonal tiling patterns. Our approach to exploring the 3D topology of 2D tessellations of a naphthalene diimide-based molecular triangle (NDI-Δ) reveals that the 2D molecular arrangement is sensitive to the identity of the solvent and solute concentrations. Tessellation of organic polygons though and charge-transfer (CT) interactions offers a unique opportunity to construct supramolecular organic electronic materials with 2D topologies.
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