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Semeik, A. S.; Berez, M. B.; Chernova, O. M.; Антина, Е. В.; Сырбу, С. А.; Lyubimova, T. V.; Kutepov, A. M.

doi:10.1023/a:1026064923515

Cited by 6 publications

(5 citation statements)

References 2 publications

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“…[19,20] Therefore, the a-free BODIPY 3 and the 3-bromo BODIPY 4 were chosen as unsymmetrical BODIPYs with one reactive position (Scheme 1; for details see Supporting Information). [21] Compounds 3 and 4 were obtained by BF 2 complexation of the corresponding dipyrrin hydrobromides 1 [22] and 2. [21] Compounds 3 and 4 were obtained by BF 2 complexation of the corresponding dipyrrin hydrobromides 1 [22] and 2.…”

Section: Resultsmentioning

confidence: 99%

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Sulfur‐Bridged BODIPY DYEmers

Ahrens¹,

Böker²,

Brandhorst³

et al. 2013

Chemistry A European J

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Reactions of BODIPY monomers with sulfur nucleophiles and electrophiles result in the formation of new BODIPY dimers. Mono- and disulfur bridges are established, and the new dyestuff molecules were studied with respect to their structural, optical, and electrochemical properties. X-ray diffraction analyses reveal individual angulated orientations of the BODIPY subunits in all cases. DFT calculations provide solution conformers of the DYEmers which deviate in a specific manner from the crystallographic results. Clear exciton-like splittings are observed in the absorption spectra, with maxima at up to 628 nm, in combination with the expected weak fluorescence in polar solvents. A strong communication between the BODIPY subunits was detected by cyclic voltammetry, where two separated one-electron oxidation and reduction waves with peak-to-peak potential differences of 120-400 mV are observed. The qualitative applicability of the exciton model by Kasha for the interpretation of the absorption spectral shape with respect to the conformational state, subunit orientation and distance, and conjugation through the different sulfur bridges, is discussed in detail for the new BODIPY derivatives. This work is part of our concept of DYEmers, where the covalent oligomerisation of BODIPY-type dye molecules with close distances is leading to new functional dyes with predictable properties.

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Section: Resultsmentioning

confidence: 99%

“…Note that the free meso ‐position of BODIPYs is reactive only towards very strong nucleophiles such as n BuLi 21. Compounds 3 and 4 were obtained by BF 2 complexation of the corresponding dipyrrin hydrobromides 1 22 and 2 . Compound 2 was prepared from 1 by treatment with elemental bromine 23…”

Section: Resultsmentioning

confidence: 99%

Sulfur‐Bridged BODIPY DYEmers

Ahrens¹,

Böker²,

Brandhorst³

et al. 2013

Chemistry A European J

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“…Furthermore, the enol tautomer of the keto group is favored because it enables the H-bond with the nitrogen lone pair. 63 Identification of specific BrC chromophores derived from GA has proven difficult due to the pronounced and diverse oligomerization reactions of GA. 64 HPLC-DAD-ESI-MS data suggests a partial conversion of GA oligomer carbonyl functions into imines as indicated by odd m/z for some of the observed oligomer signals and thus an odd number of N-atoms in the ions (data not shown). The corresponding samples showed strong colors already within the first hour of reaction time, for GA/glycine first colored products were actually visible within seconds.…”

Section: View Article Onlinementioning

confidence: 99%

“…These products show a larger conjugated p-electron system than the simple pyrrole frameworks, which leads to a bathochromic shift of the absorbance maximum to the visible region around 450 nm. 63 Identification of specific BrC chromophores derived from GA has proven difficult due to the pronounced and diverse oligomerization reactions of GA. 64 HPLC-DAD-ESI-MS data suggests a partial conversion of GA oligomer carbonyl functions into imines as indicated by odd m/z for some of the observed oligomer signals and thus an odd number of N-atoms in the ions (data not shown). In the reaction of GA with AS and glycine, we propose the formation of (N-substituted) pyridine, i.e., products 16 and 17 in Table 2, via cyclization and formation of an aromatic system after imine formation.…”

Section: The Chemistry Of the Formation Of Nitrogen Heterocycles In A...mentioning

confidence: 99%

Secondary brown carbon formation via the dicarbonyl imine pathway: nitrogen heterocycle formation and synergistic effects

Kampf

Filippi

Zuth

et al. 2016

Phys. Chem. Chem. Phys.

107

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Dicarbonyls are known to be important precursors of so-called atmospheric brown carbon, significantly affecting aerosol optical properties and radiative forcing. In this systematic study we report the formation of light-absorbing nitrogen containing compounds from simple 1,2-, 1,3-, 1,4-, and 1,5-dicarbonyl + amine reactions. A combination of spectrophotometric and mass spectrometric techniques was used to characterize reaction products in solutions mimicking atmospheric particulates. Experiments with individual dicarbonyls and dicarbonyl mixtures in ammonium sulfate and glycine solutions demonstrate that nitrogen heterocycles are common structural motifs of brown carbon chromophores formed in such reaction systems. 1,4- and 1,5-dicarbonyl reaction systems, which were used as surrogates for terpene ozonolysis products, showed rapid formation of light-absorbing material and products with absorbance maxima at ∼450 nm. Synergistic effects on absorbance properties were observed in mixed (di-)carbonyl experiments, as indicated by the formation of a strong absorber in ammonium sulfate solutions containing acetaldehyde and acetylacetone. This cross-reaction oligomer shows an absorbance maximum at 385 nm, relevant for the actinic flux region of the atmosphere. This study demonstrates the complexity of secondary brown carbon formation via the imine pathway and highlights that cross-reactions with synergistic effects have to be considered an important pathway for atmospheric BrC formation.

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“…Chemical Synthesis and Characterization of BODIPY Dyes. Compounds 1(Â3,8) and 2(Â8) 39 were prepared from the corresponding dipyrrin hydrobromides 40 according to standard procedures. CH 2 Cl 2 was dried by standard procedures and distilled from an appropriate drying agent.…”

Section: Introductionmentioning

confidence: 99%

Chemical and Electrochemical Dimerization of BODIPY Compounds: Electrogenerated Chemiluminescent Detection of Dimer Formation

et al. 2011

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The electrochemistry of several difluoroboradiaza-s-indacene (BODIPY) compounds lacking substituent groups in the meso (8)- and/or 3 (α)-positions was investigated. Chemical and electrochemical dimerization was demonstrated, and the dimerization depended on the character of substitution. The chemical dimerization was achieved by oxidative coupling using FeCl(3) in CH(2)Cl(2) at 0 °C. The electrochemical dimerization proceeded via anodic oxidation to the radical cation and monitored by both cyclic voltammetry (CV) and electrogenerated chemiluminescence (ECL). An available open 3-position was important for the formation of the dimer. The resulting 3,3'-dimer produced a second peak in the CV oxidation and also the appearance of a longer wavelength ECL peak at 656 nm, which is considerably shifted from the parent peak at 532 nm. No dimerization was seen for BODIPY molecules in which only the meso 8-position was unsubstituted, either by chemical or electrochemical means, demonstrating that dimerization occurs at position 3.

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Cited by 6 publications

References 2 publications

Sulfur‐Bridged BODIPY DYEmers

Sulfur‐Bridged BODIPY DYEmers

Secondary brown carbon formation via the dicarbonyl imine pathway: nitrogen heterocycle formation and synergistic effects

Chemical and Electrochemical Dimerization of BODIPY Compounds: Electrogenerated Chemiluminescent Detection of Dimer Formation

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