Expanding the boron peroxide chemistry on BODIPY scaffold

Prinčič, Griša G.; Lozinšek, Matic; Iskra, Jernej

doi:10.1016/j.dyepig.2021.109290

Cited by 5 publications

(4 citation statements)

References 43 publications

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“…Geometrical parameters of the unique hydrogen bonds formed by the OOH ligand as a proton donor in crystal structures of p-block element hydroperoxo complexes are summarized in Table S9. Analysis of the crystal structure databases , revealed five crystal structures of p-block element hydroperoxo complexes with localized protons demonstrating seven unique hydrogen bonds. − Crystal structures obtained in this work additionally revealed 18 unique hydrogen bonds of OOH ligands coordinated to Sb(V). The values of the O···O distances fit into a quite narrow interval of 2.643(2)–2.828(5) Å (Figure a) with a mean value of 2.751 Å [standard error of the mean ( S ) of 0.008].…”

Section: Resultsmentioning

confidence: 68%

“…According to the Cambridge Structure Database (CSD) and Inorganic Crystal Structure Database (ICSD), there are currently only eight complexes containing p-block elements with hydroperoxo ligands. Moreover, only six of these structures of boron, , silicon, germanium, tin, and lead hydroperoxo complexes have been reported with objectively defined protons. Only one well-defined crystal structure describing the coordination hydroperoxide complex with more than one OOH ligand near one coordination center has been reported to date, representing homoleptic tin hydroperoxo complex Cs 2 Sn(OOH) 6 .…”

Section: Introductionmentioning

confidence: 99%

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Organoantimony Dihydroperoxides: Synthesis, Crystal Structures, and Hydrogen Bonding Networks

et al. 2023

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Despite growing interest in the potential applications of p-block hydroperoxo complexes, the chemistry of inorganic hydroperoxides remains largely unexplored. For instance, single-crystal structures of antimony hydroperoxo complexes have not been reported to date. Herein, we present the synthesis of six triaryl and trialkylantimony dihydroperoxides [Me3Sb(OOH)2, Me3Sb(OOH)2·H2O, Ph3Sb(OOH)2·0.75(C4H8O), Ph3Sb(OOH)2·2CH3OH, pTol3Sb(OOH)2, pTol3Sb(OOH)2·2(C4H8O)], obtained by the reaction of the corresponding dibromide antimony(V) complexes with an excess of highly concentrated hydrogen peroxide in the presence of ammonia. The obtained compounds were characterized by single-crystal and powder X-ray diffraction, Fourier transform infrared and Raman spectroscopies, and thermal analysis. The crystal structures of all six compounds reveal hydrogen-bonded networks formed by hydroperoxo ligands. In addition to the previously reported double hydrogen bonding, new types of hydrogen-bonded motifs formed by hydroperoxo ligands were found, including infinite hydroperoxo chains. Solid-state density functional theory calculation of Me3Sb(OOH)2 revealed reasonably strong hydrogen bonding between OOH ligands with an energy of 35 kJ/mol. Additionally, the potential application of Ph3Sb(OOH)2·0.75(C4H8O) as a two-electron oxidant for the enantioselective epoxidation of olefins was investigated in comparison with Ph3SiOOH, Ph3PbOOH, t-BuOOH, and H2O2.

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Section: Resultsmentioning

confidence: 68%

Section: Introductionmentioning

confidence: 99%

Organoantimony Dihydroperoxides: Synthesis, Crystal Structures, and Hydrogen Bonding Networks

et al. 2023

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“…[1,2] BODIPY dyes have become important because of their small stoke shift, strong absorption, narrow emission, stable chemical structure, and ability to dissolve in organic solvents. [3] It is known that the photophysical properties of BODIPYs change if there is an electron transfer between the substituted groups attached to the BODIPY nucleus. [4] In recent years, the efficacy of BODIPYs in cancer treatment, such as photodynamic therapy (PDT), has been investigated frequently as a photosensitizer.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of water‐soluble BODIPY dyes and investigation of their DNA interaction properties and cytotoxicity/phototoxicity

Keleş

Barut

Yıldırım

et al. 2021

Applied Organom Chemis

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In this study, water‐soluble BODIPY dyes (BDPY‐4, BDPY‐5) bearing dimethylamino and diethylamino groups were synthesized for the first time. The DNA interaction and nuclease effect of two water‐soluble BODIPY dyes were examined using absorption, competitive binding experiments, and agarose gel electrophoresis. Then, cytotoxicity and phototoxicity of the compounds were determined against A549 cells by MTT cell viability assay. The ultraviolet–visible (UV–vis) spectra of BDPY‐4 and BDPY‐5 displayed hypochromism and absorption maxima shifted to the red region. In addition, Kb values of the compounds were calculated as 2.23 × 104 and 4.84 × 104 M−1, respectively. An high‐performance liquid chromatography (HPLC) instrument without a column was used to conduct competitive binding experiments for the first time. The approach prevented the decrease in the response due to dilution and enabled the analysis to be carried out in a short time. Upon increasing concentrations of the compounds, the emission intensity of EB‐DNA significantly decreased. These obtained results suggested that the compounds bound to CT‐DNA with intercalative mode. At the same time, the Stern–Volmer constants were determined as 1.80 × 106 and 1.79 × 106 M−1 for BDPY‐4 and BDPY‐5, respectively, which is coherent with intercalative binding mode. The compounds did not display noticeable photonuclease actions with light irradiation. BDPY‐4 and BDPY‐5 showed moderate phototoxic properties on light irradiation.

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“…Owing to frequently encountered exceptional reactivity of NR MOOR species, the controlled synthesis and subsequent isolation of this family of compounds still appear to be a challenge 9 – 11 . In the last three decades, a few examples of heteroleptic Group 1 12 , 2 13 – 15 , 12 16 – 21 and 13 22 – 36 metal alkylperoxides have occasionally been isolated. In particular, systematic research on the oxygenation chemistry of organozincs have marked an important milestones in a deeper understanding of the reactivity of ZnOOR species.…”

Section: Introductionmentioning

confidence: 99%

Towards deeper understanding of multifaceted chemistry of magnesium alkylperoxides

et al. 2021

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Despite considerable progress in the multifaceted chemistry of non-redox-metal alkylperoxides, the knowledge about magnesium alkylperoxides is in its infancy and only started to gain momentum. Harnessing the well-defined dimeric magnesium tert-butylperoxide [(f5BDI)Mg(μ-η2:η1-OOtBu)]2 incorporating a fluorinated β-diketiminate ligand, herein, we demonstrate its transformation at ambient temperature to a spiro-type, tetranuclear magnesium alkylperoxide [(f5BDI)2Mg4(μ-OOtBu)6]. The latter compound was characterized by single-crystal X-ray diffraction and its molecular structure can formally be considered as a homoleptic magnesium tert-butylperoxide [Mg(µ-OOtBu)2]2 terminated by two monomeric magnesium tert-butylperoxides. The formation of the tetranuclear magnesium alkylperoxide not only contradicts the notion of the high instability of magnesium alkylperoxides, but also highlights that there is much to be clarified with respect to the solution behaviour of these species. Finally, we probed the reactivity of the dimeric alkylperoxide in model oxygen transfer reactions like the commonly invoked metathesis reaction with the parent alkylmagnesium and the catalytic epoxidation of trans-chalcone with tert-butylhydroperoxide as an oxidant. The results showed that the investigated system is among the most active known catalysts for the epoxidation of enones.

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Expanding the boron peroxide chemistry on BODIPY scaffold

Cited by 5 publications

References 43 publications

Organoantimony Dihydroperoxides: Synthesis, Crystal Structures, and Hydrogen Bonding Networks

Organoantimony Dihydroperoxides: Synthesis, Crystal Structures, and Hydrogen Bonding Networks

Synthesis of water‐soluble BODIPY dyes and investigation of their DNA interaction properties and cytotoxicity/phototoxicity

Towards deeper understanding of multifaceted chemistry of magnesium alkylperoxides

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