Structural studies of meso-CF3-3(5)-aryl(hetaryl)- and 3,5-diaryl(dihetaryl)-BODIPY dyes by 1H, 13C and 19F NMR spectroscopy and DFT calculations

Afonin, A. V.; Ushakov, Igor А.; Павлов, Д. В.; Петрова, О. В.; Собенина, Л. Н.; Михалева, А. И.; Трофимов, Б. А.

doi:10.1016/j.jfluchem.2012.11.009

Cited by 13 publications

(9 citation statements)

References 52 publications

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“…Preparations of boron–fluorine complexes of pyrazolines (BOAPPY, 7–9 ) and 1,2′‐diazaflavone (BODAF, 11 ) were accomplished by reaction of new 3,5‐disubstituted‐2‐pyrazolines ( 4–6 ) and diazaflavone ( 10 ) with BF 3 .Et 2 O under inert and basic conditions according to previously reported procedure shown in Scheme . Changing of chemical shifts in the 1 H NMR, physical properties and new occurred NH– peaks near at δ 7.4 ppm in 1 H NMR and very strong B–N (∼1100 cm −1 ) and strong B–F (∼760 cm −1 ) IR‐absorption bands also supported the formation of organic boron–fluorine complexes.…”

Section: Resultsmentioning

confidence: 99%

“…The synthesis and characterizations of boradiazaindacene (BODIPY) core containing compounds and boron 2‐(2′‐pyridiyl)imidazole complexes (BOPIM) have gained great interest over the last 3 decades considering their extensive use in different applications of science and technology .…”

Section: Introductionmentioning

confidence: 99%

“…Especially, synthesis of organic boron–fluorine compounds have been main target for many researchers since they have exhibited excellent properties as dyes , fluorescent chemosensors , photodynamic therapy agent , ion sensor , sensitizers for solar cells , and energy transfer cassettes . The BOPIM dyes ( III , IV ; Fig.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Novel Pyrazolines, Their Boron–Fluorine Complexes, and Investigation of Antibacterial, Antioxidant, and Enzyme Inhibition Activities

Kahriman

Haşimoğlu

Serdaroğlu

et al. 2016

Archiv der Pharmazie

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New 3,5-disubstituted-2-pyrazoline derivatives (4-6), their boron-fluorine complexes (boron (3-(2'-aminophenyl),5-(2'-/3'-/4'-pyridyl)pyrazoline, BOAPPY) (7-9) and boron 1,2'-diazaflavone complex (BODAF) (11) were synthesized starting from azachalcones (1-3) to diazaflavone (10), respectively. Biological evaluation of compounds 4-9 and 11 showed remarkable antioxidant, antibacterial, and acetylcholinesterase and tyrosinase enzyme inhibition activities. All newly synthesized compounds 4-9 and 11 showed respectable antibacterial effect with minimum inhibitory concentrations in the range of 4.7-150 μg/mL.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of Novel Pyrazolines, Their Boron–Fluorine Complexes, and Investigation of Antibacterial, Antioxidant, and Enzyme Inhibition Activities

Kahriman

Haşimoğlu

Serdaroğlu

et al. 2016

Archiv der Pharmazie

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“…For adsorption configuration F, the Hg 0 adsorption activity of the C(57) adsorption site was low, and the C−Hg bond shifted spatially because during the adsorption process of mercury atoms, an overlapping electron cloud was formed with adjacent aldehyde functional groups. 56 Due to the repulsive force, certain atoms or groups in the molecule were close to each other, resulting in a steric hindrance effect, which further weakened the adsorption activity of the mercury atom at the adsorption site.…”

Section: Methodsmentioning

confidence: 99%

Study of the Molecular Structure and Elemental Mercury Adsorption Mechanism of Biomass Char

Guo

et al. 2020

Energy Fuels

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Based on a comprehensive study of the pyrolysis characteristics, pore structure, surface chemical functional groups, organic carbon framework structure, microcrystalline morphology, and lattice characteristics of walnut shell biochar for mercury adsorption, the structural characteristics of biochar were analyzed, and a model of the monomeric molecular structure of biochar was constructed. In addition, the density functional theory of quantum mechanics was introduced into the gas−solid adsorption reaction of elemental mercury with biochar. By quantitatively studying the adsorption energy, adsorption height, and Mulliken population number of the adsorption system, the adsorption mechanism of Hg 0 by biochar was revealed to provide a theoretical basis for future mercury removal methods. The results showed that walnut shell biochar consisted mainly of C, H, O, and N. Aromatic carbon was the main component of the biochar molecular structure, while aliphatic carbon was linked to aromatic structural units. The molecular structure model was mainly composed of aromatic structures, including one methyl, four hydroxyl, and eight carbonyl groups. The molecular formula was C 55 H 37 NO 14 , and the molecular weight was 935. The adsorption of Hg 0 by biochar was mainly via chemical adsorption, and the adsorbed Hg 0 could stably exist on the biochar surface. The Hg 0 adsorption process on the biochar surface mainly depended on the charge of the adsorption site. An adsorption site with a negative charge and with a high number of charges facilitated the adsorption of elemental mercury on the biochar surface. Moreover, the charge of the ortho atom adjacent to the adsorption site had a substantial influence on the adsorption activity of the adsorption site.

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“…Incorporation in BODIPY cores of the heavy atoms that would give rise to effective singlet oxygen generation by intersystem crossing for serving as a potential photodynamic therapy agent was also aimed. 26 Hence, a general effective route to a novel family of meso-CF 3 -3,5-diaryl-BODIPY dyes composed of four different target BODIPY molecules was designed here.…”

Section: Introductionmentioning

confidence: 99%

An exploration of new avenues regarding deep tissue penetration and highersinglet oxygen efficiencies: novel near-IR photosensitizers for photodynamictherapy

Yeşilgül¹,

Kılıç²

2019

Turk J Chem

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A series of novel BODIPY-bearing electron-withdrawing groups at the meso position are reported here. According to the optical measurements, it may be clearly seen that the introduction of electron-donating groups into 3,5-positions and the presence of electron-withdrawing groups at the meso position of the BODIPY core resulted in spectacular bathochromic shifts (up to~304 nm), and the projected photosensitizers had absorption bands in the therapeutic window of the electromagnetic spectrum (600-900 nm). The absorption maxima of compounds 4, 5, 6, and 7 were at 886 nm, 890 nm, 760 nm, and 761 nm, respectively. The singlet oxygen generation experiments revealed that compounds 6 and 7, with high singlet oxygen quantum yields (0.52 and 0.93, respectively), were excellent and promising candidates for photodynamic therapy. The singlet oxygen quantum yield of 0.93 was the highest reported value so far for BODIPY-based photosensitizers.

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Structural studies of meso-CF3-3(5)-aryl(hetaryl)- and 3,5-diaryl(dihetaryl)-BODIPY dyes by 1H, 13C and 19F NMR spectroscopy and DFT calculations

Cited by 13 publications

References 52 publications

Synthesis of Novel Pyrazolines, Their Boron–Fluorine Complexes, and Investigation of Antibacterial, Antioxidant, and Enzyme Inhibition Activities

Synthesis of Novel Pyrazolines, Their Boron–Fluorine Complexes, and Investigation of Antibacterial, Antioxidant, and Enzyme Inhibition Activities

Study of the Molecular Structure and Elemental Mercury Adsorption Mechanism of Biomass Char

An exploration of new avenues regarding deep tissue penetration and highersinglet oxygen efficiencies: novel near-IR photosensitizers for photodynamictherapy

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