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Functionalized 4,4′-Bipyridines: Synthesis and 2D Organization on Highly Oriented Pyrolytic Graphite
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    Functionalized 4,4′-Bipyridines: Synthesis and 2D Organization on Highly Oriented Pyrolytic Graphite
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2021, 86, 4, 3356–3366
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    https://doi.org/10.1021/acs.joc.0c02708
    Published February 4, 2021
    Copyright © 2021 American Chemical Society

    Abstract

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    Commercial 4,4′-bipyridine is a popular scaffold that is primarily employed as a linker in 3D self-assembled architectures such as metallo-organic frameworks or as a connector in 2D networks. The introduction of alkyl substituents on the bipyridine skeleton is instrumental when 4,4′-bipyridines are used as linkers to form 2D self-assembled patterns on surfaces. Here, several synthetic strategies to access 4,4′-bipyridines functionalized at various positions are described. These easily scalable reactions have been used to introduce a range of alkyl substituents at positions 2 and 2′ or 3 and 3′ and at positions 2,2′ and 6,6′ in the case of tetra-functionalization. Scanning tunneling microscopy studies of molecular monolayers physisorbed at the graphite–solution interface revealed different supramolecular patterns whose motifs are primarily dictated by the nature and position of the alkyl chains.

    Copyright © 2021 American Chemical Society

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.0c02708.

    • CPK model, X-ray crystallography methods and data, thermal ellipsoids, 1H and 13C NMR spectra, and mass spectra (PDF)

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    CCDC 2042158 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2021, 86, 4, 3356–3366
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.0c02708
    Published February 4, 2021
    Copyright © 2021 American Chemical Society

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