The self-assembly of the 2,2′-diamino-5,5′-(dialkylmethylidene)methylenedipyrimidine derivatives 3a – c allows for the molecular-recognition-directed generation of pleated sheets as revealed by X-ray crystallographic analysis. The data provide insight into the interplay of the different structural and interactional features of the molecular components in the generation of the supramolecular assembly. The introduction of the adamantylidene group as in 3c leads to the dominance of the H-bonding factor and the resulting formation of a regular, fully interconnected array of pleated sheet type. The results suggest further manipulation of the interplay of the different factors to induce the self-assembly of other supramolecular architectures.
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Krische et al. (1998) studied this question.