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    Synthesis of orthogonal push-pull chromophores via click reaction of arylynamines

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    Publication date
    2022-04
    End of Embargo
    2023-04-28
    Author
    Huang, S.
    Ma, J.
    Yi, Y.
    Li, M.
    Cai, P.
    Wu, Na (Anna)
    Keyword
    Click reaction
    Orthogonal push–pull chromophores
    Arylynamines
    Research Development Fund Publication Prize Award
    Rights
    © The Royal Society of Chemistry 2022. Reproduced in accordance with the publisher's self-archiving policy.
    Peer-Reviewed
    Yes
    Open Access status
    embargoedAccess
    
    Metadata
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    Abstract
    Herein, we report a catalyst-free ‘click’ reaction: metal-free [2 + 2] cycloaddition–retro-electrocyclisation (CA–RE) of arylynamines with the sluggish acceptor tetracyanoquinodimethane (TCNQ) to provide orthogonal electron-push–pull light-harvesting small molecules: N-heterocyclic dicyanoquinodimethane-substituted methylene malononitriles. Ynamines are reactive alkynes and tend to induce over-reactions with the CA–RE adducts. The reactivity of arylynamines was balanced properly by ensuring the electrondensity of the nitrogen atom was delocalised more over the aromatic rings than the triple bond.
    URI
    http://hdl.handle.net/10454/19083
    Version
    Accepted manuscript
    Citation
    Huang S, Ma J, Yi Y et al (2022) Synthesis of orthogonal push-pull chromophores via click reaction of arylynamines. Organic and Biomolecular Chemistry. 20: 4081-4085.
    Link to publisher’s version
    https://doi.org/10.1039/D2OB00677D
    Type
    Article
    Notes
    The full-text of this article will be released for public view at the end of the publisher embargo on 28 Apr 2023.
    Research Development Fund Publication Prize Award winner, April 2022.
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    Life Sciences Publications

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