A pyrenyl-appended triazole-based ribose as a fluorescent sensor for Hg2+ ion

doi:10.1016/j.carres.2010.09.010

Carbohydrate Research

Volume 345, Issue 17, 22 November 2010, Pages 2557-2561

https://doi.org/10.1016/j.carres.2010.09.010 Get rights and content

Abstract

For the efficient detection of toxic trace metal ions, two pyrenyl-appended triazole-based d-ribose fluorescent chemosensors 6 and 7 were prepared and their fluoroionophoric properties toward transition metal ions were investigated. Chemosensors 6 and 7 exhibit highly selective recognition toward Hg²⁺ ion among a series of tested metal ions in CH₂Cl₂/MeOH solution. The association constants of 6 and 7 are calculated to be 1.73 × 10⁵ M⁻¹ and 4.44 × 10⁵ M⁻¹, respectively. Both 6 and 7 formed complexes with the Hg²⁺ ion at a 1:1 ligand-to-metal ratio with a detection limit of 10–15 μM Hg²⁺. Computational analysis demonstrated that the Hg²⁺ ion occupied the coordination center of 6 with N² and N³ atoms in two triazole groups, thus separating and distorting the two parallel pyrenes away from each other.

Graphical abstract

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In consideration of these chemosensors for Hg2+ ions based on triazole derivatives, there are generally two different modes. On the one hand, these compounds bearing triazole units for recognition of Hg2+ ions exhibited the fluorescence enhancement or quenching without any variation in colour [32–38]. On the other hand, some probes showed a highly selective and sensitive response as fluorometric and colorimetric sensors towards Hg2+ ion accompanied by distinct color changes from colorless to pink [39–41], or from yellow to purple [42,43], or from yellow to brownness [44,45], or from yellow to green [46] etc, all of which provided “naked eye” detection of Hg2+.
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Taking into account the decrease in excimer and monomer emissions with the addition of Hg2+ and the conjugated triazolylpyrene based structure, we can speculate that the fluorescence quenching was probably caused by photoinduced electron transfer to pyrene either in free state or as an excimer complex. Hg2+ binding mechanism can be attributed to the complexation of Hg2+ ions by conjugated triazolylpyrene groups, which is consistent with the findings for triazole-containing Hg2+ sensors [34–37]. Scheme 2 illustrates the possible sensing mechanism for Hg2+.
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NoteA pyrenyl-appended triazole-based ribose as a fluorescent sensor for Hg2+ ion

Abstract

Graphical abstract

Environ. Res.

Carbohydr. Res.

Tetrahedron Lett.

Chem. Rev.

Am. J. Epidemol.

Neurotoxicology

Org. Lett.

Org. Lett.

Org. Lett.

Org. Lett.

Note
A pyrenyl-appended triazole-based ribose as a fluorescent sensor for Hg²⁺ ion