5-Aryl-2,2′-bipyridines as tunable fluorophores

Kozhevnikov, Dmitry N.; Shabunina, Olga V.; Kopchuk, Dmitry S.; Слепухин, П. А.; Kozhevnikov, Valery N.

doi:10.1016/j.tetlet.2006.07.111

Cited by 44 publications

(27 citation statements)

References 21 publications

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“…Selected fluorescent ligands containing bipy or its analogs: 25 [87], 26 [88], 27 [89], 28 [90], 29 [80], 30 [91], 31 [92], 32 [93], and 33 [94]. …”

Section: Figmentioning

confidence: 99%

5-Arylvinylene-2,2′-bipyridyls: Bright “push–pull” dyes as components in fluorescent indicators for zinc ions

Zhu

Younes

Zhao

et al. 2015

Journal of Photochemistry and Photobiology A: Chemistry

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This article reviews the zinc(II)-dependent photophysical properties of arylvinylbipyridines (AVBs), a class of fluoroionophores in which 2,2′-bipyridyl and an aryl moiety are electronically conjugated. Zinc(II) binding of an AVB may lead to an emission bathochromic shift of the fluoroionophore without diminishing its fluorescence quantum yield. This observation can be explained using the excited state model of electron donor–π bridge–electron acceptor “push–pull” fluorophores, in which the bipy moiety acts as an electron acceptor, and zinc(II)-coordination strengthens its electron affinity. The spectral sensitivity of bipy-containing fluoroionophores, such as AVBs, to zinc(II) can be exploited to prepare fluorescent indicators for this ion. In several cases, AVB moieties are incorporated in fluorescent heteroditopic ligands, so that the variation of zinc(II) concentration over a relatively large range can be correlated to fluorescence changes in either intensity or color. AVB fluoroionophores are also used to introduce an intramolecular Förster resonance energy transfer (FRET) strategy for creating zinc(II) indicators with high photostability and a narrow emission band, two desired characteristics of dyes used in fluorescence microscopy.

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“…Selected fluorescent ligands containing bipy or its analogs: 25 [87], 26 [88], 27 [89], 28 [90], 29 [80], 30 [91], 31 [92], 32 [93], and 33 [94]. …”

Section: Figmentioning

confidence: 99%

5-Arylvinylene-2,2′-bipyridyls: Bright “push–pull” dyes as components in fluorescent indicators for zinc ions

Zhu

Younes

Zhao

et al. 2015

Journal of Photochemistry and Photobiology A: Chemistry

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“…with D r a f t no DTTA or Eu*DTTA attached, and it can be explained by a significant contribution of n-π-transition to the excited state of the phenylbipyridine chromophore. 19 It is worthy to mention that the phosphorescence of the Eu*11 complex was not affected mainly: upon the addition of Zn(ClO 4 ) 2 we have not observed any significant changes in the intensity of the phosphorescence or any shift of the phosphorescence spectrum maxima. In contrast, the addition of Cu 2+ or Ni 2+ salts caused the significant quenching of both fluorescence and phosphorescence of the Eu*11 complex (Fig.…”

Section: R a F Tmentioning

confidence: 67%

Synthesis of a new DTTA- and 5-phenyl-2,2′-bipyridine-based ditopic ligand and its Eu³⁺ complex

et al. 2016

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A new ditopic ligand based on diethylenetriamine-N,N,N″,N″-tetraacetate (DTTA) and 5-phenyl-2,2′-bipyridine has been synthesized. The improved method for the synthesis of DTTA tert-butyl ester has been developed. The water-soluble Eu3+*DTTA complex of this ligand has been prepared, and its photophysical properties have been studied. Due to the presence of an extra chelating unit, 5-phenyl-2,2′-bipyridine, this Eu3+*DTTA complex demonstrated a strong fluorescence response to the Zn2+ cation (fluorescence enhancement) and the simultaneous fluorescent and phosphorescent response (fluorescence and phosphorescence quenching) to the Cu2+ or Ni2+ cations in aqueous solutions.

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“…223,224 When ZnCl 2 was used in place of Zn(ClO 4 ) 2 in the previous experiment, only a complex of the 1:1 stoichiometry ([Zn( 28 )Cl 2 ]) was observed. 213 …”

Section: Zn(ii) Coordination Chemistrymentioning

confidence: 95%

Zn(ii)-coordination modulated ligand photophysical processes – the development of fluorescent indicators for imaging biological Zn(ii) ions

et al. 2014

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Molecular photophysics and metal coordination chemistry are the two fundamental pillars that support the development of fluorescent cation indicators. In this article, we describe how Zn(II)-coordination alters various ligand-centered photophysical processes that are pertinent to developing Zn(II) indicators. The main aim is to show how small organic Zn(II) indicators work under the constraints of specific requirements, including Zn(II) detection range, photophysical requirements such as excitation energy and emission color, temporal and spatial resolutions in a heterogeneous intracellular environment, and fluorescence response selectivity between similar cations such as Zn(II) and Cd(II). In the last section, the biological questions that fluorescent Zn(II) indicators help to answer are described, which have been motivating and challenging this field of research.

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5-Aryl-2,2′-bipyridines as tunable fluorophores

Cited by 44 publications

References 21 publications

5-Arylvinylene-2,2′-bipyridyls: Bright “push–pull” dyes as components in fluorescent indicators for zinc ions

5-Arylvinylene-2,2′-bipyridyls: Bright “push–pull” dyes as components in fluorescent indicators for zinc ions

Synthesis of a new DTTA- and 5-phenyl-2,2′-bipyridine-based ditopic ligand and its Eu³⁺ complex

Zn(ii)-coordination modulated ligand photophysical processes – the development of fluorescent indicators for imaging biological Zn(ii) ions

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5-Aryl-2,2′-bipyridines as tunable fluorophores

Cited by 44 publications

References 21 publications

5-Arylvinylene-2,2′-bipyridyls: Bright “push–pull” dyes as components in fluorescent indicators for zinc ions

5-Arylvinylene-2,2′-bipyridyls: Bright “push–pull” dyes as components in fluorescent indicators for zinc ions

Synthesis of a new DTTA- and 5-phenyl-2,2′-bipyridine-based ditopic ligand and its Eu3+ complex

Zn(ii)-coordination modulated ligand photophysical processes – the development of fluorescent indicators for imaging biological Zn(ii) ions

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Synthesis of a new DTTA- and 5-phenyl-2,2′-bipyridine-based ditopic ligand and its Eu³⁺ complex