title: A specific chemodosimeter for fluoride ion based on a pyrene derivative with trimethylsilylethynyl groups.
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.
authors.affiliation: Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, 310012, P. R. China.
authors.forename: Hua
authors.initials: H
authors.lastname: Lu
authors.forename: Qiuhong
authors.initials: Q
authors.lastname: Wang
authors.forename: Zhifang
authors.initials: Z
authors.lastname: Li
authors.forename: Guoqiao
authors.initials: G
authors.lastname: Lai
authors.forename: Jianxiong
authors.initials: J
authors.lastname: Jiang
authors.forename: Zhen
authors.initials: Z
authors.lastname: Shen
mesh_terms: D003116:Color; D003124:Colorimetry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000378:metabolism; D005459:Fluorides / Q000032:analysis* / Q000378:metabolism; D007202:Indicators and Reagents / Q000138:chemical synthesis* / Q000378:metabolism; D015394:Molecular Structure; D011721:Pyrenes / Q000138:chemical synthesis* / Q000378:metabolism; D012680:Sensitivity and Specificity; D013050:Spectrometry, Fluorescence; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis* / Q000378:metabolism; D014867:Water / Q000032:analysis*; D014874:Water Pollutants, Chemical / Q000032:analysis*
chemical_list: D005456:Fluorescent Dyes; D007202:Indicators and Reagents; D011721:Pyrenes; D014297:Trimethylsilyl Compounds; D014874:Water Pollutants, Chemical; D014867:Water; D005459:Fluorides