Ring-Fused Malonamides as a Novel Hydrogen-bonding Motif: Construction of Supramolecular Architectures with Controlled Dimensionality

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Ring-fused malonamides with two primary amide groups, such as 2,2-indanedicarboxamides, assemble into well-defined 2D-sheet structures based on the formation of 6 to 8 hydrogen bonds per molecule. The fused ring part would be planted above and below the 2D-sheet by supporting with multiple hydrogen-bondings. The stacking manner and the interlayer distances of these sheets in crystal can be manipulated by varying the size of the fused ring, to form either interdigitated or segregated structures. Furthermore, triptycene-fused malonamides for the purpose of formation to tubular structures by rolling 2D-sheet into a cylinder due to their steric hindrance of triptycenes. We revealed their hydrogen-bonding patterns to assemble a tubluar structure by powder X-ray structural analysis. This motif technique allows the ready design of crystalline materials wherein the various functionalities are situated in well-ordered arrays.