New Heteropolycyclic Structures for Fluoride Anion Sensing by Naked-Eye Visualization

Lei Zhu, Ying Wen, Haoran Liu, Zebing Zeng, Jingzhe Zhao, Jianhui Jiang, Shaobin Miao

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

Fluoride anion (F) plays an important and fundamental role in chemical, biological, pathological, and environmental processes. It is highly desired to develop new methods for facial and efficient F detection. Herein we present the synthesis and characterization of two effective fluoride ion probes and their selective F sensing by naked-eye visualization. A N-heteroannelated anthraquinone derivative, compound I, was prepared by a cyclocondensation reaction of 1,2-diaminoanthraquinone with 1,6-bis(triisopropylsilyl)-hexa-l,5-diyne-3,4-dione. Compound I was treated with malononitrile in the presence of Lehnert reagent to afford an HCl adduct, compound II, and an aza-polycyclic aromatic compound III. All three compounds were characterized crystallographically and were studied photochemically. Similarly, 2,3-diamino-1,4-anthraquinone reacted with 1,6-bis(triisopropylsilyl)-hexa-l,5-diyne-3,4-dione to afford compound IV, which reacted with malononitrile in the presence of Lehnert reagent to yield compound V. Compounds III and V are sensitive and selective probes for the detection of F with significant color changes. The detection by naked eye visualization is rapid and facile, showing both compounds are potential probes for fluoride ion sensing.

Original languageEnglish (US)
Pages (from-to)2336-2342
Number of pages7
JournalChemistrySelect
Volume3
Issue number8
DOIs
StatePublished - Feb 28 2018

Keywords

  • Anthraquinone derivative
  • Fluoride anion probe
  • Fused-ring systems
  • Heterocycles
  • Naked-eye sensing
  • X-ray diffraction

ASJC Scopus subject areas

  • Chemistry(all)

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