Synthesis of orthogonal push-pull chromophores via click reaction of arylynamines
End of Embargo2023-04-28
Orthogonal push–pull chromophores
Research Development Fund Publication Prize Award
Rights© The Royal Society of Chemistry 2022. Reproduced in accordance with the publisher's self-archiving policy.
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AbstractHerein, 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.
CitationHuang 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 versionhttps://doi.org/10.1039/D2OB00677D
NotesThe 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.