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Aroyleneimidazophenazine: A Sensitive Probe for Detecting CN Anion and its Solvatochromism Effect

Journal of Heterocyclic Chemistry, ISSN: 1943-5193, Vol: 52, Issue: 6, Page: 1699-1704
2015
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Article Description

A novel electron-deficient heteroacene 15H-pyrazino[2:3′,4′]pyrrolo[1′,2′:1,2]imidazo[4,5-b]phenazin-15-one (1) has been successfully synthesized and characterized. Compound 1 can selectively recognize CN and F over other 10 anions including BF, PF, Cl, SO, NO, I, HPO, ClO, Ac, and Br in CHCl/DMF mixed solvents with dual responses, including absorption signals and fluorescent "turn-off" effects. CN and F can be distinguished by the completely quenched fluorescence (for CN) and partially reduced fluorescence (for F). Especially, compound 1 exhibits higher sensitivity to CN than F with the response concentration as low as 5.0 × 10 mol/L. Moreover, compound 1 shows very interesting solvatochromism effect, and the CHCl solution of compound 1 is sensitive to triethylamine, and its emission could change from green to red upon the addition of triethylamine, which is attributed to the n-π intermolecular charge-transfer interaction.

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