1,10-Phenanthroline-2,9-dicarboxylic acid diamides: synthesis, structure, and solubility

Петров, В. А.; Avagyan, Nane A.; Lamport, P. S.; Matveev, Petr I.; Evsiunina, Mariia V.; Roznyatovsky, Vitaly A.; Tarasevich, B. N.; Isakovskaya, K. L.; Ustynyuk, Yu. A.; Nenajdenko, Valentine G.

doi:10.1007/s11172-023-3834-7

Cited by 6 publications

(9 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The product was purified by column chromatography using an ethyl acetate/hexane mixture (hexane → hexane/ethyl acetate 1:1). Yield 65% (0.8 g), yellowish powder; mp 111−113 °C, R f = 0.4 (hexane:ethyl acetate 2:3); 1 N 2 ,N 9 -Bis(4-hexylphenyl)-N 2 ,N 9 -diethyl-7-fluoro-4-oxo-1,4-dihydro-1,10-phenanthroline-2,9-dicarboxamide 3e.…”

Section: Methods the Log P Values Given In Tablementioning

confidence: 99%

“…Synthesis and Analytical Data. N 2 ,N 9 -Bis(p-tolyl)-4,7difluoro-N 2 ,N 9 -diethyl-1,10-phenanthroline-2,9-dicarboxamide 2c.…”

Section: Methods the Log P Values Given In Tablementioning

confidence: 99%

“…The product was purified by column chromatography using an ethyl acetate/hexane mixture (hexane → hexane/ethyl acetate 1:1). Yield 80% (0.86 g), yellowish powder; mp 200−202 °C, R f = 0.2 (hexane:ethyl acetate 2:3); 1 H NMR (400 MHz, Benzene-d6) δ 10.19 (s, 1H, NH), 8.12 (d, J = 8.9 Hz, 1H, Phen-H 5 ), 7.59 (d, J = 10.0 Hz, 1H, Phen-H 8 ), 7.17 (d, J = 8.9 Hz, 1H, Phen-H 6 ), 7.05 (d, J = 8.1 Hz, 2H, Ar), 6.93 (d, J = 8.1 Hz, 2H, Ar), 6.74 (d, J = 8.1 Hz, 2H, Ar), 6.69 (d, J = 8.1 Hz, 2H, Ar), 5.97 (s, 1H, Phen-H 3 ), 3.87 (q, J = 7.1 Hz, 2H, N−CH 2 ), 3.75 (q, J = 7.1 Hz, 2H, N−CH 2 ), 1.92 (s, 3H, Ar−CH 3 ), 1.90 (s, 3H, Ar−CH 3 ), 1.14 (t, J = 7.1 Hz, 3H, CH 2 −CH 3 ), 1.09 (t, J = 7.1 Hz, 3H, CH 2 −CH 3 ); 13 9 -Bis(4-butylphenyl)-N 2 ,N 9 -diethyl-7-fluoro-4-oxo-1,4-dihydro-1,10-phenanthroline-2,9-dicarboxamide 3d.…”

Section: Methods the Log P Values Given In Tablementioning

confidence: 99%

“…Nowadays, there is a significant interest in 1,10-phenanthroline ligands as nitrogen-containing building blocks for coordination and organometallic chemistry. , These ligands have functionalized substituents that enhance their efficiency in separating f-elements. − Additionally, the presence of chiral centers in these ligands allows for asymmetric complex catalysis. − Half-sandwich Ru(II), Ir(III), and Rh(III) complexes with substituted 1,10-phenanthrolines have been proven to be highly effective catalysts. − Furthermore, Ru(II) complexes of substituted phenanthrolines have shown potential in treating brain cancer. , Copper(II) and nickel(II) complexes with asymmetric phenanthroline derivatives have also been extensively studied. − Unsymmetrical 1,10-phenanthrolines have been identified as promising ligands for Ru(II) complexes to act as photosensitizers in solar cells . Moreover, a Ru-complex of 4,7-diaminosubstituted 1,10-phenanthroline has been reported to be useful for selective dual-channel detection of Cu(II) ions .…”

Section: Introductionmentioning

confidence: 99%

“…N 2 ,N9 -Bis(4-butylphenyl)-N 2 ,N9 -diethyl-7-fluoro-4-oxo-1,4-dihydro-1,10-phenanthroline-2,9-dicarboxamide Neodymium Trinitrate 3d•Nd(NO 3 ) 3 . https://doi.org/10.1021/acs.inorgchem.3c02371 Inorg.…”

mentioning

confidence: 99%

See 4 more Smart Citations

4-Oxo-7-fluoro-1,10-phenanthroline-2,9-diamides: Synthesis, Structural Features, Lanthanide Complexes, and Am(III)/Ln(III) Solvent Extraction

Avagyan,

Lemport,

Roznyatovsky

et al. 2023

Inorg. Chem.

View full text Add to dashboard Cite

A highly efficient synthetic approach was developed for the synthesis of unsymmetrical 1,10-phenanthroline-2,9-diamides with two different substituents in the fourth and seventh positions of the phenanthroline core. The structures of these ligands were confirmed using various spectral methods including 2D-NMR and X-ray analysis. Quantum chemical calculations supported the presence of tautomeric forms of these ligands. Furthermore, it was discovered that these compounds exhibit polydentate ligand behavior toward lanthanide nitrates. The structural characteristics of the complexes formed between these ligands and lanthanide nitrates were investigated both in the solid state and in solution. To further understand the binding properties of these novel unsymmetrical ligands, the binding constants for potential complexes were quantitatively measured by using UV–vis spectrophotometric titration. This allowed for a comprehensive analysis of the binding affinity and stability of these complexes. Extraction experiments of f-elements were performed for symmetrical and unsymmetrical diamides. Overall, this study presents significant advancement in the synthesis and characterization of unsymmetrical 1,10-phenanthroline-2,9-diamides and provides valuable insights into their potential applications as polydentate ligands for lanthanide nitrates.

show abstract

Section: Methods the Log P Values Given In Tablementioning

confidence: 99%

“…Synthesis and Analytical Data. N 2 ,N 9 -Bis(p-tolyl)-4,7difluoro-N 2 ,N 9 -diethyl-1,10-phenanthroline-2,9-dicarboxamide 2c.…”

Section: Methods the Log P Values Given In Tablementioning

confidence: 99%