The impact of the heteroatom in a five-membered ring on the photophysical properties of difluoroborates

Grabarz, Anna; Jędrzejewska, Beata; Skotnicka, Agnieszka; Murugan, N.; Patalas, Filip; Bartkowiak, Wojciech; Jacquemin, Denis; Ośmiałowski, Borys

doi:10.1016/j.dyepig.2019.04.026

Cited by 11 publications

(13 citation statements)

References 125 publications

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“…The molar absorption coefficient (ε) of 1 (42,500) was significantly higher than for other complexes ( Table 2 ). These red-shifts of the absorption maxima position along with the high molar absorption coefficients indicate that the transitions of the R = NMe 2 derivative have a π → π* nature associated with a significant charge transfer (CT) [ 11 ].…”

Section: Resultsmentioning

confidence: 99%

“…In our previous published work, we have investigated the influence of heteroatom (X = O, S, and NMe) substitution in a five-membered heterocyclic ring on the photophysical properties of novel BF 2 complexes containing or not a dimethylamino group (R = NMe 2 ) [ 11 ]. It was shown that the fluorescence yields of the dimethylamino derivatives were much larger (up to one order of magnitude) than those of the corresponding unsubstituted compounds.…”

Section: Introductionmentioning

confidence: 99%

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Substituted 2-Phenacylbenzoxazole Difluoroboranes: Synthesis, Structure and Properties

Skotnicka

Czeleń

2020

Molecules

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Novel fluorescent dyes such as benzoxazole-boron complexes, bearing β-ketoiminate ligands, have been synthesized and characterized with a focus on the influence of a substituent on the basic photophysical properties. 1H, 11B, 13C, 15N, and 19F nuclear magnetic resonance (NMR) spectra of substituted 2-phenacylbenzoxazole difluoroboranes have been recorded and discussed. It is worth mentioning that a high correlation coefficient was found between 15N-NMR parameters and substituent constants. The photophysical properties of these new dyes have been investigated by fluorescence and ultraviolet-visible (UV-Vis) absorption spectroscopy. The geometry optimization, vibrational spectra, and the HOMO and LUMO energies were calculated based on density functional theory with the use of the B3LYP functional and 6-311++G(d,p) basis set.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Substituted 2-Phenacylbenzoxazole Difluoroboranes: Synthesis, Structure and Properties

Skotnicka

Czeleń

2020

Molecules

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“…The methods applied for the synthesis of 2-phenacylheterocycles and their difluoroboranyl derivatives (shown at Fig. 1 ) have been described in detail elsewhere 10 .…”

Section: Experimental and Theoretical Methodsmentioning

confidence: 99%

“…They owe the wide popularity to their extraordinary properties, namely large fluorescence quantum yield and easy chemical modifications. The rational design, and further, the precise tuning of these luminophore characteristics is vital and can be achieved as a consequence of the good understanding of the relationships between the molecular structure and their optical features 7 – 10 . However, even small structural modification can significantly affect the functional properties and, consequently, the applicability of dyes 11 .…”

Section: Introductionmentioning

confidence: 99%

“…The structural modification of the -carrying fluorophores studied by us before were focused on the substituent effetcs, benzannulation, geometry of the amino group, -electron conjugation, to mention a few 10 . The influence of the heterocyclic ring composition and the presence of the terminal dimethylamino group on the photophysical properties of the 2-phenacylheterocyclic precursors and their corresponding —bearing counterparts has been thoroughly investigated with the spectroscopic and theoretical approaches 10 . It has been proven that the presence of the – substituent significantly affects the position and the shape of the absorption and emission bands and strongly increases the fluorescence quantum yield.…”

Section: Introductionmentioning

confidence: 99%

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Tautomeric equilibrium, proton affinity and mass spectrometry fragmentation of flexible hydrogen-bonded precursors and rigid $$\hbox {N}\longrightarrow \hbox {BF}_2$$ fluorescent dyes

Kaczorowska

Kaczmarek‐Kędziera

Ośmiałowski

2021

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The stability of two groups of conformationally locked molecules, similar in topology, but differing only by the type of the bridge rigidifying their structure, is studied. The series of the less-rigid 2-phenacylheterocyclic compounds and their stiff difluoroboranyl derivatives are investigated for the determination of the effect of $$\hbox {NCH}_3$$ NCH 3 /S/O replacement in a five-membered heterocyclic ring and the presence of a strong electron-donating group on the tautomeric equilibrium, protonation affinity, and fragmentation pattern observed in the structural elucidation by means of mass spectrometry technique. The results of the $$\omega $$ ω B97X-D/6-311++G(d,p) calculations, the topological analysis of electron density as well as the experimental MS measurements show the importance of the number of heteroatoms, their properties, and location in the molecule for the rational design of the systems of desired stable tautomers or the favorable protonation sites. The obtained data allow for the understanding of the fundamentals of the novel highly fluorescent difluoroborates fragmentation behavior, vital for their structural elucidation with the application of high-resolution tandem mass spectrometry methods.

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N,O-bidentate BF2-enaminone complexes: Synthesis, electronic structure, photophysical properties, and biological behaviour

et al. 2023

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The impact of the heteroatom in a five-membered ring on the photophysical properties of difluoroborates

Cited by 11 publications

References 125 publications

Substituted 2-Phenacylbenzoxazole Difluoroboranes: Synthesis, Structure and Properties

Substituted 2-Phenacylbenzoxazole Difluoroboranes: Synthesis, Structure and Properties

Tautomeric equilibrium, proton affinity and mass spectrometry fragmentation of flexible hydrogen-bonded precursors and rigid $$\hbox {N}\longrightarrow \hbox {BF}_2$$ fluorescent dyes

N,O-bidentate BF2-enaminone complexes: Synthesis, electronic structure, photophysical properties, and biological behaviour

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