First Example of Fluorinated Phenanthroline Diamides: Synthesis, Structural Study, and Complexation with Lanthanoids

Molecules. 2022 Jul 23;27(15):4705. doi: 10.3390/molecules27154705.

Abstract

An efficient approach to the synthesis of diamides of 4,7-difluoro-1,10-phenanthroline-2,9-dicarboxylic acid was elaborated. Direct nucleophilic substitution with 4,7-dichloro-1,10-phenanthroline precursors opened access to difluoro derivatives in high yield. As a result, four new fluorinated ligands were prepared in up to 88% yield. Their structure was proved by a combination of spectral methods and X-ray data. A set of lanthanoid complexes was prepared to demonstrate the utility of new ligands. The structure of the complexes was studied in solid state (IR-spectroscopy, X-ray diffraction) and in solution (NMR-spectroscopy).

Keywords: complex; fluorine; lanthanoid; nucleophilic substitution; phenanthroline; structure.

MeSH terms

  • Diamide
  • Lanthanoid Series Elements* / chemistry
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Phenanthrolines* / chemistry

Substances

  • Lanthanoid Series Elements
  • Ligands
  • Phenanthrolines
  • Diamide