A Chromone-Derived Schiff-Base Ligand as Al(3+) "Turn on" Fluorescent Sensor: Synthesis and Spectroscopic Properties

J Fluoresc. 2016 Jan;26(1):345-53. doi: 10.1007/s10895-015-1720-0. Epub 2015 Nov 6.

Abstract

In this study, a novel chromone-derived Schiff-base ligand called 6-Hydroxy-3-formylchromone (2'-furan formyl) hydrazone (HCFH) has been designed and synthesized as a "turn on" fluorescent sensor for Al(3+). This sensor HCFH showed high selectivity and sensitivity towards Al(3+) over other metal ions investigated, and most metal ions had nearly no influences on the fluorescence response of HCFH to Al(3+). Additionally, the significant enhancement by about 171-fold in fluorescence emission intensity at 502 nm was observed in the presence of Al(3+) in ethanol, and it was due to the chelation-enhanced fluorescence (CHEF) effect upon complexation of HCFH with Al(3+) which inhibited the photoinduced electron transfer (PET) phenomenon from the Schiff-base nitrogen atom to chromone group. Moreover, this sensor formed a 1 : 1 complex with Al(3+) and the fluorescence response of HCFH to Al(3+) was nearly completed within 1 min. Thus, this sensor HCFH could be used to detect and recognize Al(3+) for real-time detection.

Keywords: Aluminum ion; Chef; Chromone; Fluorescent sensor; PET; Real-time detection.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aluminum / analysis*
  • Aluminum / chemistry*
  • Chromones / chemical synthesis
  • Chromones / chemistry*
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Schiff Bases / chemical synthesis
  • Schiff Bases / chemistry
  • Spectrometry, Fluorescence
  • Spectrophotometry, Ultraviolet

Substances

  • Chromones
  • Fluorescent Dyes
  • Ligands
  • Schiff Bases
  • Aluminum