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Synthesis of orthogonal push-pull chromophores via click reaction of arylynamines
Huang, S. Ma, J. Yi, Y. Li, M. Cai, P.
Huang, S.
Ma, J.
Yi, Y.
Li, M.
Cai, P.
Publication Date
2022-04
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© The Royal Society of Chemistry 2022. Reproduced in accordance with the publisher's self-archiving policy.
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2022-04-28
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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.
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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.
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Notes
Research Development Fund Publication Prize Award winner, April 2022.