Novel neutral lanthanide complexes of 5-aryl-2,2′-bipyridine-6′-carboxylic acids with improved photophysical properties

Kopchuk, Dmitry S.; Krinochkin, Alexey P.; Kozhevnikov, Dmitry N.; Слепухин, П. А.

doi:10.1016/j.poly.2016.07.025

Cited by 33 publications

(21 citation statements)

References 27 publications

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“…Thus, ligands 5d and 5e have been described by us earlier [ 20 ], and the synthesis of ligand 5b was performed on the basis of the corresponding 6-bromomethylbipyridine ( 1b ) as described earlier [ 19 ], as a result of alkylation of the DTTA ester shown at 6 [ 21 , 22 ]. In the case of the 4-tolyl-containing ligand ( 5c ), the 5-tolyl-2,2′-bipyridine-6-carboxylic acid methyl ester ( 7 ) reported above was used as a starting compound [ 23 ] ( Scheme 2 ).…”

Section: Resultsmentioning

confidence: 99%

Comparison of Photophysical Properties of Lanthanide(III) Complexes of DTTA- or DO3A-Appended Aryl-2,2′-Bipyridines

et al. 2023

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New Tb(III) and Eu(III) complexes based on aryl-2,2′-bipyridine ligands with a cyclic DO3A chelating unit appended in the alpha position of the bipyridine core were synthesized. The photophysical properties of these complexes were compared with those of complexes of ligands with identical aryl-2,2′-bipyridine chromophores, but with an acyclic DTTA residue as an additional chelating site in the alpha position of the bipyridine core. The nature of the polyaminocarboxylic acid fragments was found to have a significant influence on the luminescence. For some of the Eu(III) complexes, upon the transition from acyclic DTTA- to the cyclic DO3A-appended ligands, a noticeable increase in the intensity of Eu(III) luminescence was observed, with an increase in the quantum yield of up to 2.55 times. In contrast, for most of the Tb(III) complexes, a similar transition resulted in a noticeable decrease in the luminescence intensity of the Tb(III) cation.

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Section: Resultsmentioning

confidence: 99%

Comparison of Photophysical Properties of Lanthanide(III) Complexes of DTTA- or DO3A-Appended Aryl-2,2′-Bipyridines

et al. 2023

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“…Besides, in the Krenke method the direct condensation of cycloalkane moiety to one of the side-chain pyridine ring of terpyridine core (from the standpoint of increasing the solubility of both the resulting terpyridines and their metal complexes in organic solvents 19,20 ) could not be performed.…”

Section: '-Hydroxymethyl-5-phenyl-22'-bipyridine (17a) Yield 210 Mmentioning

confidence: 99%

“…Obviously, the preparation of bipyridines 10-13 is also possible by means of "1,2,4-triazine" methodology. In the case of 6-aryl-5H-1,2,4-triazines 14, 15 the pyridine residue can be modified by either the ester group 19 or methyl group, 24 which can be brominated further.…”

Section: '-Hydroxymethyl-5-phenyl-22'-bipyridine (17a) Yield 210 Mmentioning

confidence: 99%

Unsymmetrically functionalized 5,5″-diaryl- and 5,6,5″-triaryl-2,2′:6′,2″-terpyridines: an efficient synthetic route and photophysical properties

et al. 2017

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An efficient approach for the synthesis of 5,5″- or 5,6,5″-aryl substituted 2,2′:6′,2″-terpyridines, bearing an anneleted cyclopentene unit in one of the side-chain pyridine rings for the improved solubility in organic solvents, via their 1,2,4-triazine analogues has been developed. By using this approach, various aromatic substituents were introduced in the 2,2′:6′,2″-terpyridine core. Depending on the nature of the aromatic substituents, the obtained terpyridines exhibited an intense emission in a range of ca. 344–394 nm in acetonitrile solutions. For the most representative compounds, pronounced bathochromic shifts in both absorption and emission spectra were observed compared with previously reported substituted terpyridines.

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“…Using lanthanide coordination compounds with organic ligands including aromatic moieties is one solution to this challenge. The inclusion of pyridyl and triazole moieties in organic molecules, for example, ensures efficient energy absorption, resulting in an increase in the luminescence of metal ions via indirect excitation [14][15][16][17][18][19] . In compounds with magnetically active metal ions, triazole bridges also mediate exchange coupling between paramagnetic centers via the M-N-N-M channels, which have short metal-nitrogen and nitrogen-nitrogen connections [20][21][22][23][24] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Crystal Structure of Samarium(III)-(E)-1-phenyl-N-(4H-1,2,4-triazol-4-yl)methanimine Complex

Abu-Yamin¹

2021

JJC

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Samarium-benzylidene Schiff base adduct with the formula [Sm(NO3)3(H2O)3].2L (L= (E)-1-phenyl-N-(4H-1,2,4-triazol-4-yl) methanimine) (1) has been prepared, with two water molecules bonded to the samarium center form hydrogen bond with three molecules of title Schiff base through nitrogen atoms of the triazole rings. The chemical structure was confirmed by means of single-crystal X-ray diffraction (scXRD), FT-IR, electrical conductivity, thermogravimetric analysis (TGA), mass spectrometry and elemental analysis. The title complex 1 crystallizes in the triclinic P-1 space group. The unit cell parameters are a = 10.4045(1) Å, b = 12.5403(1) Å, c = 12.5477(2) Å,  = 96.668(1)o,  = 110.810(1)o,  = 111.567(1)o, V = 1.788 Å3, Z = 2, Rgt(F) = 0.0223, wRref(F2) = 0.0576. The samarium ion is in a distorted capped square antiprism environment, coordinated by three bidentate nitrates and three coordination water molecules. The [Sm(H2O)3(NO3)3] complex and the (E)-1-phenyl-N-(4H-1,2,4-triazol-4-yl)methanimine) moiety (L) are held together via hydrogen interactions to form a 2-D supramolecular framework. It is a non-electrolyte as indicated by its molar conductivity (ΛM= 10.1 S cm2 mol-1) in MeOH at 1.0 mM. The mass spectral results confirm the suggested structure of the investigated adduct.

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Novel neutral lanthanide complexes of 5-aryl-2,2′-bipyridine-6′-carboxylic acids with improved photophysical properties

Cited by 33 publications

References 27 publications

Comparison of Photophysical Properties of Lanthanide(III) Complexes of DTTA- or DO3A-Appended Aryl-2,2′-Bipyridines

Comparison of Photophysical Properties of Lanthanide(III) Complexes of DTTA- or DO3A-Appended Aryl-2,2′-Bipyridines

Unsymmetrically functionalized 5,5″-diaryl- and 5,6,5″-triaryl-2,2′:6′,2″-terpyridines: an efficient synthetic route and photophysical properties

Synthesis, Characterization and Crystal Structure of Samarium(III)-(E)-1-phenyl-N-(4H-1,2,4-triazol-4-yl)methanimine Complex

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