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Issue 21, 2012
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Highly selective colorimetric sensing of cyanide based on formation of dipyrrin adducts

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Abstract

Cyanide sensing has attracted increasing interest due to its toxicity and wide use in industrial activities. Herein, we developed three colorimetric cyanide sensors by the modification of the α-position of a dipyrrin chromophore with various carbonyl groups, namely, C6F5CO, C6H5CO and CHO for 1, 2 and 3, respectively. In dichloromethane, these sensors respond to both CN and F with distinct colour changes. UV-Vis, 1H NMR and HRMS measurements imply a two-process interaction between the sensors and CN. Initially, CN forms a hydrogen bond with the NH moiety, and then it attacks the carbonyl group of the sensors via a nucleophilic addition reaction. In contrast, in aqueous systems, only cyanide induced vivid solution colour changes from light yellow to pink via nucleophilic addition reactions. The CN detection limits reach a micromolar level of 3.6 × 10−6 M, 4.2 × 10−6 M and 7.1 × 10−6 M for 1, 2 and 3, respectively. In view of the easy synthesis and the highly selective recognition of CN with vivid colour changes, 1–3 may be developed as a novel and promising prototype of selective and sensitive colorimetric cyanide sensors.

Graphical abstract: Highly selective colorimetric sensing of cyanide based on formation of dipyrrin adducts

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Publication details

The article was received on 10 Feb 2012, accepted on 27 Mar 2012 and first published on 27 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB25297J
Citation: Org. Biomol. Chem., 2012,10, 4201-4207
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    Highly selective colorimetric sensing of cyanide based on formation of dipyrrin adducts

    Y. Ding, T. Li, W. Zhu and Y. Xie, Org. Biomol. Chem., 2012, 10, 4201
    DOI: 10.1039/C2OB25297J

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