Isatin-1,8-Naphthalimide Hydrazones: A Study of Their Sensor and ON/OFF Functionality

Molecules. 2019 Jan 22;24(3):397. doi: 10.3390/molecules24030397.

Abstract

Five novel hydrazones derived from substituted isatins were synthesized as potential anion sensors. Using UV-VIS, FTIR, NMR and fluorescence spectroscopy, these compounds' tautomeric equilibrium and Z-E photoisomerization were studied in DMF and CHCl₃, depending on the hydrazone concentrations, the presence of basic anions and light stimulation. Anion recognition aspects (PF₆-, HSO₄-, Br-, Cl-, NO₃-, F- and CH₃COO-) and these receptors' detection limits were also studied. We also tested the light-stimulated ON-OFF functionality of these compounds in the presence or absence of these anions.

Keywords: UV-Vis spectroscopy; anion sensors; intramolecular interaction; on/off switches.

MeSH terms

  • Anions / chemistry
  • Hydrazones / chemistry*
  • Isatin / chemistry*
  • Isomerism
  • Molecular Structure
  • Naphthalimides / chemistry*
  • Spectrum Analysis / methods

Substances

  • Anions
  • Hydrazones
  • Naphthalimides
  • Isatin