Water-soluble luminescent lanthanide complexes based on C6-DTTA-appended 5-aryl-2,2′-bipyridines

Krinochkin, Alexey P.; Kopchuk, Dmitry S.; Кim, Grigory А.; Шевырин, Вадим А.; Santra, Sougata; Rahman, Matiur; Taniya, Olga S.; Русинов, В. Л.; Чупахин, О. Н.

doi:10.1016/j.poly.2020.114473

Cited by 10 publications

(4 citation statements)

References 30 publications

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“…Unfortunately, these methods represent the only examples of benzofurotriazine derivatives, and provide poor yields of the desired products. At the same time, 1,2,4-triazines represent readily accessible and cheap building blocks for the construction of pyridine [ 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 ], pyrimidine [ 63 , 64 ] or pyrazine [ 59 , 65 , 66 ] cores via the sequence of Diels-Alder/ retro -Diels-Alder reactions.…”

Section: Introductionmentioning

confidence: 99%

MnO2-Mediated Oxidative Cyclization of “Formal” Schiff’s Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines

et al. 2022

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A different type of MnO2-induced oxidative cyclization of dihydrotriazines has been developed. These dihydrotriazines are considered as a “formal” Schiff’s base. This method provided easy access to naphthofuro-fused triazine via the C-C/C-O oxidative coupling reaction. The reaction sequence comprised the nucleophilic addition of 2-naphthol or phenol to 1,2,4-triazine, followed by oxidative cyclization. The scope and limitations of this novel coupling reaction have been investigated. Further application of the synthesized compound has been demonstrated by synthesizing carbazole-substituted benzofuro-fused triazines. The scalability of the reaction was demonstrated at a 40 mmol load. The mechanistic study strongly suggests that this reaction proceeds through the formation of an O-coordinated manganese complex.

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Section: Introductionmentioning

confidence: 99%

MnO2-Mediated Oxidative Cyclization of “Formal” Schiff’s Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines

et al. 2022

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“…The chlorine content needed for the elemental analysis of ligands was measured using the mercurimetry method. Compounds 1b [ 19 ], 1d-e [ 20 ], 1f [ 14 ], 1g [ 15 ], 1h [ 16 ], 1i [ 18 ], 5d-e [ 20 ], DTTA ester 6 [ 21 , 22 ], and 7 [ 23 ] were synthesized as described in the literature.…”

Section: Experimental Methodsmentioning

confidence: 99%

“…For these complexes, there is a requirement that saturation of all coordination bonds of the lanthanide cation is met, and this has been repeatedly confirmed by calculations based on the values of the luminescence lifetime in water and heavy water (D 2 O). To create these complexes, chromophores such as unsubstituted 2,2′-bipyridine [ 9 ], 7- tert -butyl-2-(2-pyridyl)-5 H -chromeno [2,3- b ]pyridin-5-one [ 10 ], 9-methyl-1,10-phenanthroline [ 11 , 12 ], and its 4,7-diphenyl derivative [ 13 ], as well as 10,11,12,13-tetrahydrodipyrido [3,2- a :2′,3′- c ]phenazine [ 10 ] and various aryl-containing 2,2′-bipyridines [ 14 , 15 , 16 , 17 , 18 , 19 ], have been used.…”

Section: Introductionmentioning

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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“…Early we reported on our progress in the development in this direction. E.g., the chromophore systems with aromatic substituent at position C6′ [8], C4 [9][10][11], C5 [12] and C5′ [6] have been researched for effectiveness of lanthanide cations sensibilization. As a result, the main regularities of the influence of the bipyridine chromophore structure on the properties of the complexes were revealed.…”

Section: Introductionmentioning

confidence: 99%

Improved method for the obtaining DTTA-appended 2,2’-bipyridine ligands for lanthanide cations

et al. 2022

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The composition of the reaction mixture after DTTA tert-butyl ester alkylation with 6'-halomethyl-5-phenyl-2,2'-bipyridines was studied. In addition to the target product, DTTA-appended 2,2’-bipyridine, the corresponding 6'-hydroxymethyl-substituted 2,2’-bipyridine and (5'-phenyl-[2,2'-bipyridin]-6-yl)methyl formate were isolated as by-products in some cases. Finally, an improved procedure for the DTTA tert-butyl ester alkylation with 6'-halomethyl-5-phenyl-2,2'-bipyridines by using Finkelstein reaction was developed.

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Water-soluble luminescent lanthanide complexes based on C6-DTTA-appended 5-aryl-2,2′-bipyridines

Cited by 10 publications

References 30 publications

MnO2-Mediated Oxidative Cyclization of “Formal” Schiff’s Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines

MnO2-Mediated Oxidative Cyclization of “Formal” Schiff’s Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines

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

Improved method for the obtaining DTTA-appended 2,2’-bipyridine ligands for lanthanide cations

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