Synthesis and Optical Properties of Difluorobora‐<i>s</i>‐diazaindacene Dyes with Trifluoromethyl <i>meso‐</i>Substituents

Собенина, Л. Н.; Петрова, О. В.; Petrushenko, Konstantin B.; Ushakov, Igor А.; Михалева, А. И.; Méallet‐Renault, Rachel; Трофимов, Б. А.

doi:10.1002/ejoc.201300212

Cited by 29 publications

(15 citation statements)

References 49 publications

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“…A similar phenomenon was also found in a previous report, i.e., one additional methyl group red-shifted the absorption and emission maxima by about 2.01 × 10 2 cm −1 and 1.64 × 10 2 cm −1 , respectively [45]. It violated the general assertion that as a weak electron donating group, the methyl group generally has little effect on wavelengths of fluorescent dyes.…”

Section: Resultssupporting

confidence: 82%

A Straightforward Substitution Strategy to Tune BODIPY Dyes Spanning the Near-Infrared Region via Suzuki–Miyaura Cross-Coupling

Otsuka

Matsumiya

et al. 2018

Materials

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In this study, a series of new red and near-infrared (NIR) dyes derived from 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) were developed by introducing thiophene and its derivatives to the 3- and 5- positions of the dichloroBODIPY core. For the first time, cyclictriol boronates and N-methyliminodiacetic acid (MIDA) boronate were used as organoboron species to couple with 3,5-dichloroBODIPY via the one-step Suzuki–Miyaura cross-coupling. Six kinds of thieno-expended BODIPY dyes were synthesized in acceptable yields ranging from 31% to 79%. All six dyes showed different absorption and emission wavelengths spanning a wide range (c.a. 600–850 nm) in the red and NIR regions with relatively high quantum yields (19–85%). Cellular imaging of 8-(2,6-dimethylphenyl)-re3,5-di(2-thienyl)-BODIPY (dye 1) was conducted using bovine cumulus cells, and the fluorescence microscopy images indicated that the chromophore efficiently accumulated and was exclusively localized in the cytoplasm, suggesting it could be utilized as a subcellular probe. All six dyes were characterized using 1H-NMR and mass spectrometry.

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Section: Resultssupporting

confidence: 82%

A Straightforward Substitution Strategy to Tune BODIPY Dyes Spanning the Near-Infrared Region via Suzuki–Miyaura Cross-Coupling

Otsuka

Matsumiya

et al. 2018

Materials

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“…It is worth noting that N,4,5-unsubstituted 2,3-diarylpyrroles are difficult to synthesize and are useful precursors for boron-dipyrromethenes (BODIPYs), an important class of highly fluorescent dyes. [14] Thef ormation of compounds 4 should involve the reaction of ketimine products with the solvent DMF.T o clarify the reaction mechanism, as eries of control experiments and isotope-labelling experiments were performed. For instance,m ono-13 C-labelled DMF,H…”

Section: Angewandte Chemiementioning

confidence: 99%

α‐Arylation of Ketimines with Aryl Sulfides at a Low Palladium Catalyst Loading

2016

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Instead of using aryl halides, aryl sulfides, typically poisonous to transition-metal catalysts, were found to serve as aryl electrophiles in the catalytic α-arylation of ketimines, a class of carbonyl derivatives. Low catalyst loadings (down to 0.5 mol %) of a palladium-NHC complex are sufficient for efficient arylation. α-Arylated ketimine products are useful for the synthesis of various azaarenes, including 2,3-diarylpyrroles, an indole, and pyrrolediones.

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“…Recently, we synthesized a series of brightly fluorescent 3,5‐diphenyl‐8‐CF 3 ‐BODIPY derivatives with high fluorescence quantum yields (0.7–1.0) between 600 and 650 nm. The positions of the spectral bands were fine‐tuned by simple auxochromic substituents (R=H, Cl, CH 3 , OCH 3 ) at the para positions of one or both phenyl rings in the BODIPY core …”

Section: Introductionmentioning

confidence: 99%

Environment‐Responsive 8‐CF₃‐BODIPY Dyes with Aniline Groups at the 3 Position: Synthesis, Optical Properties and RI‐CC2 Calculations

et al. 2017

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The spectroscopic and the photophysical properties of isomeric environment-sensitive BODIPYd erivatives in different solvents are reported. The simultaneous presence of the stronge lectron-acceptorC F 3 and electron-donor NH 2 group in the structure of BODIPY,a sw ell as the positiono f the NH 2 group on the aryl ring, showedasignificante ffect on the spectroscopic and fluorescence characteristics of the BODIPY chromophore, both experimentally and theoretically. The comparison of meta and para derivatives (1a and 1b) shows that, in both cases, they have av ery low quantum yield (F f )a nd fluorescencel ifetime (t f )i nt he solvents used (except for n-hexane), therefore, they are potentially suitable as turn-onf luorescences ensors. The twisted intramolecular charge transfer (TICT) mechanism was adopted to explain solvate-induced fluorescence quenching. Besides this, there is as trong pH dependence on the photophysical behavior of the two isomers, which could also lead to applications as pH sensors. On the other hand, only 1a can be au seful probe for CO 2 sensing.O wing to aw eaker electron-donor character of the NHCOMe group in comparison with the NH 2 group, the position of the fluorescence "off-on" threshold of BODIPY 1c and 1d is shifted to the side of more polar solvents than for 1a and 1b.

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Synthesis and Optical Properties of Difluorobora‐s‐diazaindacene Dyes with Trifluoromethyl meso‐Substituents

Cited by 29 publications

References 49 publications

A Straightforward Substitution Strategy to Tune BODIPY Dyes Spanning the Near-Infrared Region via Suzuki–Miyaura Cross-Coupling

A Straightforward Substitution Strategy to Tune BODIPY Dyes Spanning the Near-Infrared Region via Suzuki–Miyaura Cross-Coupling

α‐Arylation of Ketimines with Aryl Sulfides at a Low Palladium Catalyst Loading

Environment‐Responsive 8‐CF₃‐BODIPY Dyes with Aniline Groups at the 3 Position: Synthesis, Optical Properties and RI‐CC2 Calculations

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Synthesis and Optical Properties of Difluorobora‐s‐diazaindacene Dyes with Trifluoromethyl meso‐Substituents

Cited by 29 publications

References 49 publications

A Straightforward Substitution Strategy to Tune BODIPY Dyes Spanning the Near-Infrared Region via Suzuki–Miyaura Cross-Coupling

A Straightforward Substitution Strategy to Tune BODIPY Dyes Spanning the Near-Infrared Region via Suzuki–Miyaura Cross-Coupling

α‐Arylation of Ketimines with Aryl Sulfides at a Low Palladium Catalyst Loading

Environment‐Responsive 8‐CF3‐BODIPY Dyes with Aniline Groups at the 3 Position: Synthesis, Optical Properties and RI‐CC2 Calculations

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Environment‐Responsive 8‐CF₃‐BODIPY Dyes with Aniline Groups at the 3 Position: Synthesis, Optical Properties and RI‐CC2 Calculations