A family of supramolecular reagents containing two different binding sites, pyridine and amino-pyrimidine, were allowed to react with iodo- or bromo-substituted benzoic acids in order to assemble individual molecules into larger architectures with precise intermolecular interactions, using a combination of hydrogen- and halogen-bonds. The hydrogen-bond based amino-pyrimidine/carboxylic acid or amino-pyrimidinium/carboxylate synthons are responsible for the assembly of the primary structural motif in every case (7/7 times, 100% supramolecular yield), while Icdots, three dots, centeredN, Brcdots, three dots, centeredN, and Icdots, three dots, centeredO, halogen bonds play a structural supporting role by organizing these supermolecules into extended 1-D and 2-D architectures (5/7 times, 71% supramolecular yield). These results illustrate how two different non-covalent interactions can be employed side-by-side in the reliable construction of extended molecular solid-state networks with predictable connectivity and dimensionality.
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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2724020 | PMC |
http://dx.doi.org/10.1021/cg8006712 | DOI Listing |
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