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Issue 12, 2011
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A specific chemodosimeter for fluoride ion based on a pyrene derivative with trimethylsilylethynyl groups

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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, ClO4, H2PO4 and HPO42. 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.

Graphical abstract: A specific chemodosimeter for fluoride ion based on a pyrene derivative with trimethylsilylethynyl groups

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Publication details

The article was received on 29 Jan 2011, accepted on 30 Mar 2011 and first published on 31 Mar 2011


Article type: Paper
DOI: 10.1039/C1OB05164D
Citation: Org. Biomol. Chem., 2011,9, 4558-4562

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    A specific chemodosimeter for fluoride ion based on a pyrene derivative with trimethylsilylethynyl groups

    H. Lu, Q. Wang, Z. Li, G. Lai, J. Jiang and Z. Shen, Org. Biomol. Chem., 2011, 9, 4558
    DOI: 10.1039/C1OB05164D

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