A specific chemodosimeter for fluoride ion based on a pyrene derivative with trimethylsilylethynyl groups.
A specific chemodosimeter for fluoride ion based on a pyrene derivative with trimethylsilylethynyl groups.
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DOI：
10.1039/c1ob05164d
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发表时间：
2011-06
影响因子：
3.2
通讯作者：
Hua Lu;Qiuhong Wang;Zhifang Li;G. Lai;Jianxiong Jiang;Zhen Shen
中科院分区：
文献类型：
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作者：
Hua Lu;Qiuhong Wang;Zhifang Li;G. Lai;Jianxiong Jiang;Zhen Shen
合成了含有四个三甲基硅基乙炔基取代基的芘衍生物1，并研究了其作为氟离子显色和荧光化学剂量计传感器的作用。与其他阴离子（例如Cl（-）、Br（-）、ClO（4）（-）、H（2）PO（4）（-）和HPO（4）（2-））相比，1对氟化物阴离子在快速响应时间内表现出高灵敏度和特定选择性。TD-DFT计算表明，Si中σ-电子的离域使1的HOMO能级不稳定，从而使其吸收和发射光谱发生红移。F（-）的加入使化合物1的三甲基硅取代基被去除，并使化合物1的吸收光谱和荧光光谱发生蓝移，这可以通过肉眼观察到化合物1的颜色变化来判断。此外，通过将滤纸浸入1的THF溶液中而获得的易于制备的试纸可用于检测和估计水中氟离子的浓度。
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.