850089-97-3Relevant academic research and scientific papers
Novel pentafluorophenyl- And alkoxyphenyl-appended 2,2'-bipyridine push-pull fluorophores: A convenient synthesis and photophysical studies
Moseev, Timofey D.,Nikiforov, Egor A.,Varaksin, Mikhail V.,Starnovskaya, Ekaterina S.,Savchuk, Maria I.,Nikonov, Igor L.,Kopchuk, Dmitry S.,Zyryanov, Grigory V.,Chupakhin, Oleg N.,Charushin, Valery N.
, p. 3597 - 3607 (2021/06/21)
A convenient method for the synthesis of new highly in non-polar solvents soluble photoactive pentafluorophenyl-substituted and extended alkoxyphenyl-substituted 2,2'-bipyridines is reported. The synthetic strategy for the preparation of such ligands involves a sequence of several structural transformations, such as O-alkylation, nucleophilic substitution of hydrogen (S NH) in 1,2,4-triazine precursors via the 'addition-elimination' scheme, and the subsequent conversion of the obtained 1,2,4-triazines into 2,2'-bipyridines by means of the aza-Diels-Alder reaction. The photophysical properties of the synthesized novel pentafluoroaryl-substituted 2,2'-bipyridines were comprehensively studied. The obtained photophysical data indicate the competitive advantages of the herein reported pentafluoroarylated push-pull fluorophores, bearing extended aliphatic moieties, over their analogues containing benzoxy or phenolic fragments in terms of improvement in quantum yield and well-pronounced positive solvatochromism confirmed by the mathematical analysis according to the Lippert-Mataga equation.
The discovery of pyridinium 1,2,4-triazines with enhanced performance in bioconjugation reactions
Siegl, Sebastian J.,Dzijak, Rastislav,Vázquez, Arcadio,Pohl, Radek,Vrabel, Milan
, p. 3593 - 3598 (2017/07/10)
1,2,4-Triazines have recently been identified as versatile dienes participating in the inverse electron-demand Diels-Alder reaction with strained dienophiles. However, their widespread utility in bioconjugation reactions is still limited. Herein, we repor
Facile synthesis of 6-aryl-3-pyridyl-1,2,4-triazines as a key step toward highly fluorescent 5-substituted bipyridines and their Zn(II) and Ru(II) complexes
Kozhevnikov, Valery N.,Shabunina, Olga V.,Kopchuk, Dmitry S.,Ustinova, Maria M.,K?nig, Burkhard,Kozhevnikov, Dmitry N.
, p. 8963 - 8973 (2008/12/22)
A wide series of substituted bipyridines were obtained through the synthesis of 1,2,4-triazines and their aza Diels-Alder reactions. The reported method facilitates the synthesis of functionally diverse bipyridines that provides fine-tuning of photophysical properties of new ligands and their Zn(II) and Ru(II) complexes. Some of substituted bipyridines exhibit 'off-on' fluorescence response toward Zn2+ cations.
An efficient route to 5-(hetero)aryl-2,4′- and 2,2′-bipyridines through readily available 3-pyridyl-1,2,4-triazines
Kozhevnikov, Valery N.,Kozhevnikov, Dmitry N.,Shabunina, Olga V.,Rusinov, Vladimir L.,Chupakhin, Oleg N.
, p. 1791 - 1793 (2007/10/03)
A new route to substituted bipyridines based on a new method for the synthesis of substituted 3-pyridyl-1,2,4-triazines and their aza-Diels-Alder reactions is shown to be an efficient strategy for the preparation of structurally diverse bipyridine ligands.
