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

Hua Lu, Qiuhong Wang, Zhifang Li, Guoqiao Lai, Jianxiong Jiang, Zhen Shen

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58 Citations (Scopus)

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 2PO 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.

Original languageEnglish
Pages (from-to)4558-4562
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number12
DOIs
Publication statusPublished - 2011 Jun 21
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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