A New Protocol for the Synthesis of New Thioaryl-Porphyrins Derived from 5,10,15,20-Tetrakis(pentafluorophenyl)porphyrin: Photophysical Evaluation and DNA-Binding Interactive Studies

Molecules. 2018 Oct 10;23(10):2588. doi: 10.3390/molecules23102588.

Abstract

A new protocol for the preparation of thioaryl-porphyrins is described. The compounds were prepared from different disulfides employing NaBH₄ as a reducing agent. The methodology allowed the preparation of four different thioaryl-porphyrins in very-good to excellent yields under soft conditions, such as short reaction times and smooth heating. Additionally, the photophysical properties of new compounds were determined and experimental and theoretical DNA interactions were assessed.

Keywords: DNA interaction; disulfides; photophysical characterization; thioaryl-porphyrins.

MeSH terms

  • DNA / chemistry*
  • Kinetics
  • Light*
  • Molecular Docking Simulation
  • Porphyrins / chemical synthesis*
  • Porphyrins / chemistry
  • Quantum Theory
  • Singlet Oxygen / chemistry
  • Spectrometry, Fluorescence
  • Spectrophotometry, Ultraviolet

Substances

  • Porphyrins
  • meso-tetra(pentafluorophenyl)porphyrin
  • Singlet Oxygen
  • DNA