First Example of Fluorinated Phenanthroline Diamides: Synthesis, Structural Study, and Complexation with Lanthanoids
Nane A Avagyan1, Pavel S Lemport1, Konstantin A Lysenko1
1Department of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russia.
Molecules (Basel, Switzerland)
|July 28, 2022
Summary
Researchers developed a new synthesis for fluorinated phenanthroline ligands. These novel compounds, 4,7-difluoro-1,10-phenanthroline-2,9-dicarboxylic acid diamides, show high yields and potential in lanthanoid complex applications.
Area of Science:
- Organic Synthesis
- Coordination Chemistry
- Materials Science
Background:
- 1,10-phenanthroline derivatives are crucial ligands in coordination chemistry.
- Fluorinated organic compounds offer unique electronic and steric properties.
- Efficient synthesis of functionalized phenanthrolines is essential for developing new materials.
Purpose of the Study:
- To develop an efficient synthetic route for diamides of 4,7-difluoro-1,10-phenanthroline-2,9-dicarboxylic acid.
- To prepare and characterize novel fluorinated phenanthroline ligands.
- To explore the utility of these ligands in forming lanthanoid complexes.
Main Methods:
- Nucleophilic aromatic substitution reactions using 4,7-dichloro-1,10-phenanthroline precursors.
- Spectroscopic characterization (NMR, IR) and X-ray diffraction for structural elucidation.
- Synthesis and characterization of lanthanoid complexes.
Main Results:
- Four new fluorinated ligands were synthesized in high yields (up to 88%).
- Structural confirmation of ligands and their lanthanoid complexes using spectral and X-ray data.
- Demonstrated the formation and characterization of various lanthanoid complexes.
Conclusions:
- An efficient synthesis for novel fluorinated phenanthroline ligands was established.
- The prepared ligands are suitable for constructing lanthanoid complexes with well-defined structures.
- These findings open avenues for new fluorinated ligand design in coordination chemistry.
More Related Videos
13:21Preparation, Purification, and Characterization of Lanthanide Complexes for Use as Contrast Agents for Magnetic Resonance Imaging
Published on: July 21, 2011
15.1K
14:11Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
6.3K
Related Concept Videos
01:20Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
2.0K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.0K
02:42Valence Bond Theory
9.1K
Coordination compounds and complexes exhibit different colors, geometries, and magnetic behavior, depending on the metal atom/ion and ligands from which they are composed. In an attempt to explain the bonding and structure of coordination complexes, Linus Pauling proposed the valence bond theory, or VBT, using the concepts of hybridization and the overlapping of the atomic orbitals. According to VBT, the central metal atom or ion (Lewis acid) hybridizes to provide empty orbitals of suitable...
9.1K
01:13Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
6.3K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
6.3K
01:19Diazonium Group Substitution: –OH and –H
2.9K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.9K
00:43Complexometric Titration: Ligands
1.1K
Different monodentate and polydentate ligands are used as complexing agents in complexometric titration reactions. The formation of complexes by mono- and bidentate ligands involves two or more intermediate steps, limiting their use as complexing agents. In comparison, polydentate ligands can form complexes with metal ions in a single-step process, facilitating sharper end points. This means polydentate ligands, such as amino carboxylic acid derivatives, are most commonly employed in...
1.1K
01:14Photoluminescence: Applications
479
Photoluminescence offers a wide range of applications due to its inherent sensitivity and selectivity. This technique allows for both direct and indirect analyses of the analyte. Direct quantitative analysis is possible when the analyte exhibits a favorable quantum yield for fluorescence or phosphorescence. However, an indirect analysis may be feasible if the analyte is not fluorescent or phosphorescent, or if the quantum yield is unfavorable. Indirect methods include reacting the analyte with...
479