Synthesis of orthogonal push-pull chromophores via click reaction of arylynamines
Publication date
2022-04End of Embargo
2023-04-28Keyword
Click reactionOrthogonal push–pull chromophores
Arylynamines
Research Development Fund Publication Prize Award
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© The Royal Society of Chemistry 2022. Reproduced in accordance with the publisher's self-archiving policy.Peer-Reviewed
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embargoedAccess
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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.Version
Accepted manuscriptCitation
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/D2OB00677DType
ArticleNotes
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.