Stabilities of a series of dipyrrin difluoroborates in protic solvents in the ground and electron-excited states

Aksenova, Iu. V.; Kuznetsova, R. T.; Tel’minov, E. N.; Mayer, G. V.; Антина, Е. В.; Berezin, Mikhail Y.

doi:10.1134/s0036024416020023

Cited by 8 publications

(2 citation statements)

References 22 publications

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“…In this context, ag eneral survey of the scientificl iterature on the chemical stability of BODIPYs allowed us to identifya tl east two structurala spects with an influence on their stability.T hus, the degree of peripheral alkyl-substitution on the BODIPY core [27] and the presence of an 8-aryl substituent, [28,29] have long been known to stabilize the fluorophore. On the other hand, substitution at boron has also been identified as ak ey factor determining the stabilityo fB ODIPYs.…”

Section: Resultsmentioning

confidence: 99%

BODIPYs as Chemically Stable Fluorescent Tags for Synthetic Glycosylation Strategies towards Fluorescently Labeled Saccharides

Uriel

Permingeat

Ventura

et al. 2020

Chemistry A European J

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As eries of fluorescent boron-dipyrromethene (BODIPY,4,,4a-diaza-s-indacene)d yes have been designed to participate, as aglycons, in synthetic oligosaccharide protocols. As such, they served ad ual purpose:f irst, by being incorporated at the beginning of the process( at the reducing-endof the growing saccharide moiety), they can function as fluorescent glycosyl tags, facilitating the detection and purification of the desired glycosidic intermediates,a nd secondly,t he presence of these chromophores on the ensuing compounds grants access to fluorescently labeled saccharides. In this context, as ought-after feature of the fluorescent dyes has been their chemical robustness. Accordingly, some BODIPY derivatives described in this work can withstand the reactionc onditions commonly employed in the chemical synthesiso fs accharides;n amely, glycosylation and protecting-group manipulations. Regarding their photophysical properties,t he BODIPY-labeled saccharides obtained in this work display remarkable fluorescence efficiency in water,r eaching quantum yield values up to 82 %, as well as notable lasing efficienciesa nd photostabilities.[a] Dr.

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Section: Resultsmentioning

confidence: 99%

BODIPYs as Chemically Stable Fluorescent Tags for Synthetic Glycosylation Strategies towards Fluorescently Labeled Saccharides

Uriel

Permingeat

Ventura

et al. 2020

Chemistry A European J

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“…Taking into account the results of the work in [34,35], which discussed the mechanisms of protonation of such compounds, to assess the stability of dpm complexes, we chose the value −lg[HCl] 50 . In this case, the concentration of the complexes decreases due to their decomposition by 50% with the formation of a protonated ligand and the release of the complexing agent from the complex.…”

Section: Methodsmentioning

confidence: 99%

Stability of Dibromo-Dipyrromethene Complexes Coordinated with B, Zn, and Cd in Solutions of Various Acidities

Aksenova

Pomogaev

2022

Molecules

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The spectral luminescent properties of dipyrromethenates halogenated with bromine on both ends of the long axis and coordinated using boron fluoride, zinc, or cadmium in neutral ethanol and acidified with hydrochloric acid solutions were studied. The constants of the acid–base equilibrium of the complexes in the proton-donor solvents in the ground and excited states was determined. The mechanisms of complex protonation were discussed, depending on the structure of the compounds. The electronic structures of the neutral and protonated compounds were modeled and analyzed based on the quantum-chemical method. The structures and spectral-luminescence properties were calculated using the SMD model of ethanol solvent using the TD-DFT theory with the B3LYP functional and the composite def2-SVP/def2-TZVP/def2-TZVPP_ECP basis sets, depending on the atomic number of the elements.

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Effect of ms-substitution on aggregation behavior and spectroscopic properties of BODIPY dyes in aqueous solution, Langmuir-Schaefer and poly(methyl methacrylate) thin films

Antina

Ksenofontov

Kazak

et al. 2021

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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Stabilities of a series of dipyrrin difluoroborates in protic solvents in the ground and electron-excited states

Cited by 8 publications

References 22 publications

BODIPYs as Chemically Stable Fluorescent Tags for Synthetic Glycosylation Strategies towards Fluorescently Labeled Saccharides

BODIPYs as Chemically Stable Fluorescent Tags for Synthetic Glycosylation Strategies towards Fluorescently Labeled Saccharides

Stability of Dibromo-Dipyrromethene Complexes Coordinated with B, Zn, and Cd in Solutions of Various Acidities

Effect of ms-substitution on aggregation behavior and spectroscopic properties of BODIPY dyes in aqueous solution, Langmuir-Schaefer and poly(methyl methacrylate) thin films

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