Synthesis and luminescence properties of lanthanide(III) chelates with polyacid derivatives of thienyl-substituted terpyridine analogues

Yuan, Jingli; Tan, Mingqian; Wang, Guilan

doi:10.1016/j.jlumin.2003.08.001

Cited by 24 publications

(7 citation statements)

References 35 publications

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“…The overall quantum yields of the metal-centered luminescence, Φ, upon excitation of the terpyridine group are given in Table . The Φ value found for the unsubstituted terpyridinyl chelate 5 is relatively high and quite competitive with those recently reported in the literature for Eu(III) complexes derived from podands, macrocycles, cryptands, or polyaminocarboxylic ligands and sensitized by various chromophores. More significantly, the functionalization of the terpyridine group in ligands 6 and 7 does not change the capacity of the antenna to sensitize efficiently the luminescence of the europium ion in aqueous solution.…”

Section: Resultssupporting

confidence: 70%

Direct Access to Terpyridine-Containing Polyazamacrocycles as Photosensitizing Ligands for Eu(III) Luminescence in Aqueous Media

et al. 2005

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[reaction: see text] The synthesis of new 18-membered hexaazamacrocycles containing a functionalized 2,2':6',2' '-terpyridine moiety as part of the cyclic backbone and three acetate pendant arms is described. The reported synthetic procedure is based on the use of an efficient metal template ion effect which controls the macrocyclization step. This procedure is compatible with some functional groups present in the macrocyclic structure. The photophysical properties of the Eu(III) complexes derived from these ligands were examined in aqueous solutions. Their luminescence lifetimes (tau approximately 1 ms) and quantum yields (13% < Phi < 18%) on one hand, their high kinetic inertness on the other hand, and the presence of additional functionality allowing their covalent conjugation to biomolecules seriously nominate these complexes as very promising candidates for luminescent labeling of biological materials.

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Section: Resultssupporting

confidence: 70%

Direct Access to Terpyridine-Containing Polyazamacrocycles as Photosensitizing Ligands for Eu(III) Luminescence in Aqueous Media

et al. 2005

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“…This has most commonly been performed using Claisen-Schmidt condensation of various aromatic aldehydes − with 2-acetylpyridine to give the ( E )-propen-2-enones 8 (Scheme ). Their reaction with N -[2-(pyrid-2-yl)-2-oxoethyl]pyridinium iodide and sodium acetate in methanol yielded the terpyridine derivatives 9a − d .…”

Section: The Chromophorementioning

confidence: 99%

Bioconjugation with Stable Luminescent Lanthanide(III) Chelates Comprising Pyridine Subunits

Hovinen

Guy

2008

Bioconjugate Chem.

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The use of long-lifetime emitting lanthanide(III) chelate labels or probes together with time-resolved fluorometry in detection provides a method to generate sensitive bioaffinity assays. However, the use of stable chelates demands very complicated optimization of the chelate structure. A great number of chelates have been synthesized, but usually, only the most prominent structures were then converted to corresponding biomolecule labeling reactants. This review covers the syntheses of luminescent lanthanide chelates comprising a pyridine subunit that allow solution and solid-phase bioconjugation.

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“…To design a luminescent lanthanide chelate as an analytical probe, we must fulfill the following requirements: (i) presence of a suitable absorbing group for strong luminescence with a large luminescence quantum yield and a molar extinction coefficient, in addition to a long luminescence lifetime; (ii) high thermodynamic and kinetic inertness; (iii) solubility in aqueous buffer. Recently, many luminescent lanthanide chelates have been synthesized, − and several classes of the chelates, such as preorganized and predisposed macrocyclic ligands including cryptands and cyclens, multidentate podands, , or self-assembled lanthanide triple helicates, meet these requirements. Some of these chelates are applied as sensors of pH, p O 2 , and selected anions such as halides , and as labeling reagents.…”

Section: Introductionmentioning

confidence: 99%

New Luminescent Europium(III) Chelates for DNA Labeling

et al. 2006

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The new europium(III) chelate [2,2',2'',2'''-[[4'-(aminobiphenyl-4-yl)-2,2':6',2''-terpyridine- 6,6''-diyl]bis(methylenenitrilo)]tetrakis(acetato)] europium(III) (ATBTA-Eu3+) and its 4,6-dichloro-1,3,5-triazinyl and succinimidyl derivatives (DTBTA and NHS-ATBTA, respectively) were synthesized and characterized. Both labeling complexes DTBTA-Eu3+ and NHS-ATBTA-Eu3+ are luminescent. Especially DTBTA-Eu3+ is strongly luminescent, with a luminescence quantum yield of 9.1%, molar extinction coefficient of 3.1 x 10(4) cm(-1) M(-1) (335 nm), and luminescence lifetime of 1.02 ms. The excitation and emission maximum wavelengths of DTBTA-Eu3+ are 335 and 616 nm, respectively. The complex is very stable in aqueous buffers, with a conditional formation constant log K(DTBTA-Eu) of 25.0 at pH 8, and can be conjugated to DNA and proteins. The chelates are also highly resistant to thermal decomposition, photodegradation, and ozone oxidation. These properties prove that DTBTA-Eu3+ is suitable as a luminescence label in DNA assays.

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Synthesis and luminescence properties of lanthanide(III) chelates with polyacid derivatives of thienyl-substituted terpyridine analogues

Cited by 24 publications

References 35 publications

Direct Access to Terpyridine-Containing Polyazamacrocycles as Photosensitizing Ligands for Eu(III) Luminescence in Aqueous Media

Direct Access to Terpyridine-Containing Polyazamacrocycles as Photosensitizing Ligands for Eu(III) Luminescence in Aqueous Media

Bioconjugation with Stable Luminescent Lanthanide(III) Chelates Comprising Pyridine Subunits

New Luminescent Europium(III) Chelates for DNA Labeling

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