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The cis- and trans-configurational isomers of 3 are designed and investigated as chemodosimeters for CN ions for the first time. The cis-3 reveals a NIR absorbance at 717 nm (vs. trans-3, 620 nm), and such a configurational difference can be attributed to the acidity as well as position of the binding site (CH group). A probable sensing mechanism involving cyanide-driven carbanion electron-transfer oxidation is proposed.

Graphical abstract: Anion binding modes in cis–trans-isomers of a binding site–fluorophore–π-extended system

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