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).
Funder
Russian Foundation for Basic Research
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Cited by
9 articles.
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1. First 4,7-oxygenated 1,10-phenanthroline-2,9-diamides: synthesis, tautomerism and complexation with REE nitrates;Dalton Transactions;2024
2. 4-Oxo-7-fluoro-1,10-phenanthroline-2,9-diamides: Synthesis, Structural Features, Lanthanide Complexes, and Am(III)/Ln(III) Solvent Extraction;Inorganic Chemistry;2023-10-17
3. New Macrocyclic Bis-1,10-phenanthroline-2,9-dicarboxamides. Synthesis and Stereodynamics in Solution;Russian Journal of Organic Chemistry;2023-10
4. First 24-Membered Macrocyclic 1,10-Phenanthroline-2,9-Diamides—An Efficient Switch from Acidic to Alkaline Extraction of f-Elements;International Journal of Molecular Sciences;2023-06-17
5. Pyrrolidine-Derived Phenanthroline Diamides: An Influence of Fluorine Atoms on the Coordination of Lu(III) and Some Other f-Elements and Their Solvent Extraction;International Journal of Molecular Sciences;2023-03-14