Control of Assembly of Dihydropyridyl and Pyridyl Molecules via Directed Hydrogen Bonding

Jian Lü, Li-Wei Han, Nada H. Alsmail, Alexander J. Blake, William Lewis, Rong Cao, Martin Schroder

    Research output: Contribution to journalArticlepeer-review

    Abstract

    The crystallization of two dihydropyridyl molecules, 1,4-bis(4-(3,5-dicyano-2,6-dipyridyl)dihydropyridyl)benzene ([C40H24N10]·2DMF, 1·2DMF; DMF = dimethylformamide) and 1,4-bis(4-(3,5-dicyano-2,6-dipyridyl)dihydropyridyl)phenylbenzene ([C46H28N10]·2DMF, 3·2DMF), and their respective oxidized pyridyl analogues, 1,4-bis(4-(3,5-dicyano-2,6-dipyridyl)pyridyl)benzene ([C40H20N10], 2) and 1,4-bis(4-(3,5-dicyano-2,6-dipyridyl)pyridyl)phenylbenzene ([C46H24N10]·DMF, 4·DMF), has been achieved under solvothermal conditions. The dihydropyridyl molecules are converted to their pyridyl products via in situ oxidative dehydrogenation in solution. The structures of the four molecules have been fully characterized by single crystal and powder X-ray diffraction. The oxidized pyridyl products, 2 and 4, are more elongated due to aromatization of the dihydropyridyl rings at each end of their parent molecules 1 and 3, respectively. The solid-state supramolecular structures of the pyridyl molecules are distinct from the dihydropyridyl molecules in terms of their hierarchical assembly via hydrogen bonding due to the loss of primary N–H hydrogen bond donors in the two electron oxidized tectons. Overall, the geometrically shorter molecules 1 and 3 display close-packed structures, whereas the more extended 2 and 4 assemble into more open supramolecular systems.
    Original languageEnglish
    Pages (from-to)4219-4224
    Number of pages5
    JournalCrystal Growth & Design
    Volume15
    Issue number9
    DOIs
    Publication statusPublished - 28 Jul 2015

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