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  • Title: A specific chemodosimeter for fluoride ion based on a pyrene derivative with trimethylsilylethynyl groups.
    Author: Lu H, Wang Q, Li Z, Lai G, Jiang J, Shen Z.
    Journal: Org Biomol Chem; 2011 Jun 21; 9(12):4558-62. PubMed ID: 21526250.
    Abstract:
    Pyrene derivative 1 containing four trimethylsilylethynyl substituents was synthesized and investigated as a chromogenic and fluorescent chemodosimeter sensor for fluoride ions. 1 showed a high sensitivity and specific selectivity over a rapid response time toward fluoride anions compared to other anions, such as Cl(-), Br(-), ClO(4)(-), H(2)PO(4)(-) and HPO(4)(2-). TD-DFT calculations showed that the delocalization of the σ-electrons of the silicon destabilized the HOMO energy level of 1, thus red shifting both its absorption and emission spectrum. The addition of F(-) removed the trimethylsilyl substituents and resulted in a blue shift of both the absorption and fluorescent spectra of 1, which could be monitored by the color change with the naked-eye. Moreover, an easy to prepare test paper, which was obtained by immersing a filter paper into a THF solution of 1, could be utilized to detect and estimate the concentration of fluoride anions in water.
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