BODIPY Dyes and Their Derivatives:  Syntheses and Spectroscopic Properties

Loudet, Aurore; Burgess, Kevin

doi:10.1021/cr078381n

Cited by 4,546 publications

(3,328 citation statements)

References 232 publications

Supporting

Mentioning

3,170

Contrasting

Unclassified

Order By: Relevance

“…To further test the general applicability of the sulphide-trapping chemical strategy and to develop a fluorescent probe with visible-wavelength excitation and emission, we employed 4,4-Difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene (BODIPY) as the second fluorophore template owing to its high brightness and photostability 17 . We synthesized the BODIPY-based probe SFP-2 (20) as shown in Figure 3.…”

Section: Synthesis and Fluorescent Measurements Of Sfp-2mentioning

confidence: 99%

Selective fluorescent probes for live-cell monitoring of sulphide

et al. 2011

View full text Add to dashboard Cite

Aqueous sulphides, including hydrogen sulphide, have important roles in biological signalling and metabolic processes. Here we develop a selective sulphide-trapping strategy involving sulphide addition to an aldehyde; the resulting hemithioacetal undergoes a michael addition with an adjacent unsaturated acrylate ester to form a thioacetal at neutral pH in aqueous solution. Employing this new strategy, two sulphide-selective fluorescent probes, sFP-1 and sFP-2, were synthesized on the basis of two different fluorophore templates. These probes exhibit an excellent fluorescence increase and an emission maximum shift (sFP-1) in response to na 2 s and H 2 s in a high thiol background as found under physiological conditions. We show the utility of the probes for the selective detection of sulphides, and the capacity of our probes to monitor enzymatic H 2 s biogenesis and image free sulphide in living cells.

show abstract

Section: Synthesis and Fluorescent Measurements Of Sfp-2mentioning

confidence: 99%

Selective fluorescent probes for live-cell monitoring of sulphide

et al. 2011

View full text Add to dashboard Cite

show abstract

“…Highly fluorescent dyes based, for example, on rhodamine,6, 7 fluorescein,3, 8 oxazine,3 coumarin,3 cyanine9, 10 or boron dipyrromethene (BODIPY)11, 12, 13, 14, 15 chromophores, have been extensively explored along these lines. In particular, BODIPY derivatives (Scheme 1 A) became the focus of different fields due to a combination of remarkable photophysical properties, which included very high quantum yields, narrow absorption and emission bands, and high molar absorption coefficients.…”

Section: Introductionmentioning

confidence: 99%

A Three‐Component Assembly Promoted by Boronic Acids Delivers a Modular Fluorophore Platform (BASHY Dyes)

Santos

Rosa

Candeias

et al. 2015

Chemistry A European J

104

View full text Add to dashboard Cite

The modular assembly of boronic acids with Schiff‐base ligands enabled the construction of innovative fluorescent dyes [boronic acid salicylidenehydrazone (BASHY)] with suitable structural and photophysical properties for live cell bioimaging applications. This reaction enabled the straightforward synthesis (yields up to 99 %) of structurally diverse and photostable dyes that exhibit a polarity‐sensitive green‐to‐yellow emission with high quantum yields of up to 0.6 in nonpolar environments. These dyes displayed a high brightness (up to 54 000 m −1 cm−1). The promising structural and fluorescence properties of BASHY dyes fostered the preparation of non‐cytotoxic, stable, and highly fluorescent poly(lactide‐co‐glycolide) nanoparticles that were effectively internalized by dendritic cells. The dyes were also shown to selectively stain lipid droplets in HeLa cells, without inducing any appreciable cytotoxicity or competing plasma membrane labeling; this confirmed their potential as fluorescent stains.

show abstract

“…The success of BODIPY dyes is easily understandable taking into account their many outstanding properties, including bright fluorescence (due to high fluorescence quantum yields Φ combined with large molar absorption coefficients ε(λ)), good chemical and photostability in solution and in the solid state, remarkable redox characteristics, resistance towards self-aggregation in solution, fluorescence lifetimes in the nanosecond range, excitation/emission wavelengths in the visible region, narrow emission bandwidths with high peak intensities and negligible triplet state population. 4,5 Another major reason for the vast increase in popularity of these dyes is that these properties can be modified by chemical derivatization of the BODIPY core (at the pyrrole ring positions, the central meso-position and the boron atom). There are two main routes to substituted BODIPY compounds: either one starts from suitably functionalized pyrroles 6,7 or one postfunctionalizes the BODIPY core.…”

Section: Introductionmentioning

confidence: 99%

UV—vis spectroscopy of the coupling products of the palladium-catalyzed C—H arylation of the BODIPY core

Wang

Verbelen

Tonnelé

et al. 2013

Photochem Photobiol Sci

View full text Add to dashboard Cite

The steady-state, UV-vis electronic absorption and fluorescence emission properties of a large set of 3-aryl and 3,5-diaryl substituted difluoroboron dipyrromethene dyes obtained via direct, palladiumcatalyzed C-H (het)arylation of the BODIPY core are reported. The spectra display the narrow absorption and fluorescence emission bands and the generally quite small Stokes shifts characteristic of classic difluoroboron dipyrrins. As a function of the solvent, the spectral maxima are located within a very narrow wavelength range and are slightly red-shifted with increasing solvent polarizability, which is shown to be the crucial parameter influencing the wavelength position of the maxima. The extended π-conjugation in the 3,5-diaryl products always leads to bathochromically shifted absorption and emission spectra compared to those of the 3-aryl analogues. The derivative with a 3-mesityl substituent has blue-shifted spectra in comparison to its 3-phenyl substituted analogue, reflecting the diminished π-conjugation in the former due to steric strain. The nature of the meso-aryl has only a small effect on the spectral positions but affects the fluorescence quantum yield Φ. The majority of the dyes have high Φ (>0.85), except the compounds with meso-phenyl and meso-( p-nitrophenyl) substituents. Quantumchemical calculations were performed to evaluate the differences in spectroscopic properties upon substitution of the BODIPY core and to compare them with the corresponding experimental results.

show abstract

BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties

Cited by 4,546 publications

References 232 publications

Selective fluorescent probes for live-cell monitoring of sulphide

Selective fluorescent probes for live-cell monitoring of sulphide

A Three‐Component Assembly Promoted by Boronic Acids Delivers a Modular Fluorophore Platform (BASHY Dyes)

UV—vis spectroscopy of the coupling products of the palladium-catalyzed C—H arylation of the BODIPY core

Contact Info

Product

Resources

About