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Triazoliptycenes: A Twist on Iptycene Chemistry for Regioselective Cross-Coupling To Build Nonstacking Fluorophores
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    Triazoliptycenes: A Twist on Iptycene Chemistry for Regioselective Cross-Coupling To Build Nonstacking Fluorophores
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    Department of Chemistry, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul, 08826, Korea
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    Organic Letters

    Cite this: Org. Lett. 2017, 19, 23, 6380–6383
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    https://doi.org/10.1021/acs.orglett.7b03239
    Published November 16, 2017
    Copyright © 2017 American Chemical Society

    Abstract

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    Triazoliptycene fluorophores have been designed and synthesized, in which a three-dimensional propeller-like iptycene motif is employed to suppress intermolecular π–π stacking in the solid state. Key to the success of this modular synthesis is a stereoelectronic bias imposed by the iptycene scaffold, which assists the desired regioselectivity in the C–N cross-coupling step as the last-stage structure diversification from a common precursor.

    Copyright © 2017 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.7b03239.

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    CCDC 15792271579231 and 15792331579234 contain 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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    This article is cited by 15 publications.

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    Organic Letters

    Cite this: Org. Lett. 2017, 19, 23, 6380–6383
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.7b03239
    Published November 16, 2017
    Copyright © 2017 American Chemical Society

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