Borondifluoride complexes of hemicurcuminoids as bio-inspired push-pull dyes for bioimaging.

@article{Kim2016BorondifluorideCO,
  title={Borondifluoride complexes of hemicurcuminoids as bio-inspired push-pull dyes for bioimaging.},
  author={Eunsun Kim and Abdellah Felouat and Elena Zaborova and Jean Charles Ribierre and Jeong Weon Wu and S{\'e}bastien S{\'e}natore and C{\'e}dric Matthews and Pierre-François Lenne and Carole Baffert and Artak Karapetyan and Michel Giorgi and Denis Jacquemin and Miguel Ponce-Vargas and Boris le Guennic and Fr{\'e}d{\'e}ric Fages and Anthony D'Al{\'e}o},
  journal={Organic \& biomolecular chemistry},
  year={2016},
  volume={14 4},
  pages={
          1311-24
        }
}
Hemicurcuminoids are based on half of the π-conjugated backbone of curcuminoids. The synthesis of a series of such systems and their borondifluoride complexes is described. The electrochemical and photophysical properties of difluorodioxaborine species were investigated as a function of the nature of electron donor and acceptor groups appended at either terminal positions of the molecular backbone. The emissive character of these dipolar dyes was attributed to an intraligand charge transfer… 
View on PubMed
rsc.org
31 Citations
Background Citations
5
Results Citations
1

31 Citations

Citation Type

Citation Type

Boron Difluoride Curcuminoid Fluorophores with Enhanced Two-Photon Excited Fluorescence Emission and Versatile Living-Cell Imaging Properties.
TLDR
Overall, this structure-relationship study allows the optimization of the two-photon brightness with one dye that emits in the NIR region of the spectrum with high intracellular uptake efficiency in Cos7 cells with emission in the visible region.
Ethynylene-analogues of hemicurcuminoids: Synthesis and ground- and excited properties of their boron difluoride complexes
Photophysical and Photoacoustic Properties of Quadrupolar Borondifluoride Curcuminoid Dyes.
The synthesis and characterization of a series of donor-π-acceptor-π-donor (D-A-D) curcuminoid molecules is presented herein that incorporates π-extended aryl and electron-donating amino terminal…
Multi-stimuli-responsive fluorescence of a highly emissive difluoroboron complex in both solution and solid states
A highly fluorescent emissive difluoroboron complex (TC) was designed, synthesized and characterized. The absolute fluorescence quantum yields of TC are 33.0% in the solid state and 26.0% in the…
Polarization effect in luminescent mesogenic BF2 complexes derived from heterocyclic benzothiazoles
Theoretical and Experimental Study on Boron β-Diketonate Complexes with Intense Two-Photon-Induced Fluorescence in Solution and in the Solid State.
TLDR
Three boron diketonate chromophores with extended π-conjugated backbone were prepared and their spectroscopic features were investigated, and it was shown that the two-photon absorption properties were dominated by the quadrupolar term.
Synthesis and photophysical properties of conformationally restricted difluoroboron β-diketonate complexes of 1-indanone derivatives
Modulation of the Photophysical Properties of β-substituted BODIPY Dyes
TLDR
For the synthesized BODIPY dyes fluorescence quantum yields and lifetimes show very sharp decrease with an increase in the solvent polarity, suggesting the involvement of highly polar ICT state de-excitation mechanism along with the local excitation process.
Photochemically-assisted synthesis and photophysical properties of difluoroboronated β-diketones with fused four-benzene-ring chromophores, chrysene and pyrene.
TLDR
It was found that PyB is fluorescent, whereas the fluorescence quantum yields of the ChBs depend on the substituted position of the chrysene moiety, which is shown to be of a charge-transfer character.
Exciton Interactions, Excimer Formation and [2π+2π] Photodimerization in Nonconjugated Curcuminoid-BF2 Dimers.
TLDR
This work describes the synthesis of a series of covalently-linked dimers of quadrupolar curcuminoid-BF2 dyes and the detailed investigation of their solvent-dependent spectroscopic and photophysical properties, and represents the first example of a [2π+2π] photodimerization of the curCuminoid chromophore.
...
1
2
3
4
...

References

SHOWING 1-10 OF 47 REFERENCES
NIR Emission in Borondifluoride Complexes of 2'-Hydroxychalcone Derivatives Containing an Acetonaphthone Ring
We report the synthesis of borondifluoride complexes of a series of 2′-hydroxychalcone derivatives containing the hydroxynaphthone ring. TD-DFT calculations confirm the charge transfer character of…
Syntheses and photophysical properties of BF2 complexes of curcumin analogues.
TLDR
A new class of curcumin-BF2 complexes has been prepared from the condensation of 2,2-difluoro-1,3-dioxaborylpentadione with a variety of aldehydes and its photophysical properties were characterized.
Boron difluoride complexes of 3-hydroxyflavone derivatives: efficient bioinspired dyes for solution and solid-state emission.
  • A. D'Aléo, F. Fages
  • Chemistry
    Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology
  • 2013
TLDR
A series of six boron difluoride complexes of 3-hydroxyflavone derivatives is described and light emission from the π-stacked molecules was quenched relative to the solution behaviour, interpreted in terms of both packing and electronic properties of the molecular dyes.
Two-photon excited fluorescence of BF2 complexes of curcumin analogues: toward NIR-to-NIR fluorescent organic nanoparticles
The synthesis of borondifluoride complexes of curcuminoids and one- and two-photon absorption properties of 1 and 2 are described. These compounds allow the preparation of organic nanoparticles that…
Efficient NIR-light emission from solid-state complexes of boron difluoride with 2'-hydroxychalcone derivatives.
TLDR
A series of nine complexes of boron difluoride with 2'-hydroxychacone derivatives possessing a set of very interesting properties that make them promising solid-state NIR fluorophores for applications in materials science.
Fluorescent carboxylic and phosphonic acids: comparative photophysics from solution to organic nanoparticles.
TLDR
These studies evidence for the first time through time-resolved fluorescence measurements the stronger H-donating character of phosphonic acids compared to the carboxylic ones, and provide information on the degree of structural heterogeneity within the nanoparticles.
Synthesis and photophysical properties of difluoroboron complexes of curcuminoid derivatives bearing different terminal aromatic units and a meso-aryl ring.
TLDR
The synthesis of nine curcuminoids and their difluoroboron complexes is described, with seven of them containing a meso-phenyl ring, and the influence of the mesonyl group on the emission properties of the aggregated solids is reported.
Phosphorescent heavy-metal complexes for bioimaging.
TLDR
This critical review systematically evaluates the advantages of phosphorescent heavy-metal complexes as bioimaging probes, including their photophysical properties, cytotoxicity and cellular uptake mechanisms.
High-sensitivity naphthalene-based two-photon fluorescent probe suitable for direct bioimaging of H2S in living cells.
TLDR
A new two-photon bioimaging probe 6-(benzo[d]thiazol-2'-yl)-2-azidonaphthalene (NHS1) for H2S with improved sensitivity and high selectivity is reported, demonstrating its value of practical application in biological systems.
Synthesis of a self organizable curcumin derivative and investigation of its interaction with metals in 100% aqueous media
...
1
2
3
4
5
...