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  • Title: Highly selective colorimetric sensing of cyanide based on formation of dipyrrin adducts.
    Author: Ding Y, Li T, Zhu W, Xie Y.
    Journal: Org Biomol Chem; 2012 Jun 07; 10(21):4201-7. PubMed ID: 22522605.
    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, C(6)F(5)CO, C(6)H(5)CO and CHO for 1, 2 and 3, respectively. In dichloromethane, these sensors respond to both CN(-) and F(-) with distinct colour changes. UV-Vis, (1)H 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.
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