Search Results (10)

The novel benzanthrone derivative, 2-bromo-3-aminobenzo[de]anthracene-7-one (2-Br-3-NH₂BA), was synthesized and extensively characterized to investigate its photophysical behavior in various solvents. It was prepared through selective bromination of 3-aminobenzanthrone using N-bromosuccinimide in dimethylformamide at −20 °C. Featuring a donor–π–acceptor (D–π–A) structure, 2-Br-3-NH₂BA exhibits pronounced solvatochromism due to the intramolecular charge transfer (ICT) between the amino donor and the carbonyl acceptor groups. Optical measurements conducted in eight solvents of varying polarity revealed a significant bathochromic shift in both absorption and fluorescence emission, with emission maxima red-shifting by over 110 nm from non-polar to polar environments. Corresponding reductions in the optical band gap energies, as calculated from Tauc plots, further support solvent-induced electronic state modulation. Additionally, quantum yield analysis showed higher fluorescence efficiency in non-polar solvents, while polar solvents induced twisted intramolecular charge transfer (TICT), leading to emission quenching. These findings demonstrate the sensitivity of 2-Br-3-NH₂BA to environmental polarity, making it a promising candidate for color-tunable luminescent applications in optoelectronics and sensing. However, further studies in the solid state are required to validate its applicability in device architectures such as OLEDs. Full article

In this research, we explore the synthesis of and characterize α-aminophosphonates derived from anthraquinone and benzanthrone, focusing on their fluorescence properties and potential applications in confocal laser scanning microscopy (CLSM). The synthesized compounds exhibit notable solvatochromic behavior, emitting fluorescence from green to red across various solvents. Spectroscopic analysis, including ¹H-, ¹³C-, and ³¹P-NMR, FTIR, and mass spectrometry, confirms the chemical structures. The compounds’ toxicity is evaluated using etiolated wheat sprouts, revealing varying degrees of impact on growth and oxidative damage. Furthermore, the study introduces these α-aminophosphonates for CLSM imaging of the parasitic flatworm Opisthorchis felineus, demonstrating their potential in visualizing biological specimens. Additionally, an X-ray crystallographic study of an anthraquinone α-aminophosphonate provides valuable structural insights. Full article

In the present study, new fluorophores based on disubstituted benzanthrone derivatives were designed starting from 9-nitro-3-bromobenzanthrone with nucleophilic substitution of the bromine atom with some secondary cyclic amines. It has been found that this reaction is positively affected by the presence of a nitro group in comparison with 3-bromobenzanthrone. The new compounds exhibit intense absorption and pronounced luminescent properties in various organic solvents. In this regard, their photophysical properties were evaluated with an experimental study of the solvatochromic behavior of the obtained compounds in various solvents. It has recently been found that the addition of an electron-withdrawing nitro group to the benzanthrone core increases its first- and second-order hyperpolarizability. Such dyes can be used in the fabrication of optical limiter devices. Therefore, the developed fluorescent molecules have a potential prospect for extensive application in optoelectronics. Full article

Emissions of PAH, nitro-PAHs, and oxy-PAHs from a diesel engine fueled with diesel-biodiesel-ethanol blends need to be controlled and reduced, as they are unregulated emissions harmful to the environment and human health. The objective of this work was to investigate the effect of ethanol concentration on diesel engine emissions when fueled with diesel–biodiesel–ethanol blends. Ethanol was added with biodiesel–diesel blends. Diesel B7 and two ternary blends, B7E3 and B7E10, with 3% and 10% ethanol, were tested and studied in a diesel engine to determine engine performance characteristics and particulate matter emissions and to quantify polycyclic aromatic compounds (PACs) associated with PM_1.0 and PM_2.5. Under the same engine conditions, 18 PAHs, 27 nitro-PAHs, and 6 quinones (oxy-PAHs) were determined by GC–MS in real samples obtained from the engine. The mean concentrations of PACs found in the B7, B7E3, and B7E10 blends for PM_1.0 ranged from 0.1 µg m⁻³ (coronene) to 118.1 µg m⁻³ (2-nitrofluorene). The concentrations for PM_2.5 ranged from 0.1 µg m⁻³ (acenaphthylene) to 99.7 µg m⁻³ (2-nitrofluorene). Potent mutagens benzanthrone (BA) and 3-nitrobenzanthrone (3-NBA) were found at concentrations ranging from 0.10 µg m⁻³ to 1.9 µg m⁻³ and 0.3 µg m⁻³ to 1.6 µg m⁻³, respectively. Low molecular weight (LMW) PAHs were mainly PACs bounded to the PM_1.0 and PM_2.5 particles emitted by B7E10. Flow properties were improved by adding 3% and 10% ethanol to biodiesel. B7E3 and B7E10 blends presented low fuel consumption and a reduction in the emission factor (EF) by the engine. B7E10 blending showed a smaller total concentration of ∑PAH (26.8 µg m⁻³), ∑nitro-PAH (85.4 µg m⁻³), and ∑oxy-PAH (6.0 µg m⁻³) associated with PM_2.5 particles compared PM_1.0. Full article

The present work describes the synthesis of the new benzanthrone dye-3-[4-(2-phenylethyl)piperazin-1-yl]-7H-benzo[de]anthracen-7-one by bromine atom nucleophilic substitution reaction. The structure of the obtained benzanthrone derivative is characterized by NMR spectroscopy, mass spectrometry, and X-ray diffraction analysis. The photophysical properties of the target compound are investigated by means of UV-Vis and fluorescence spectroscopy in various organic solvents. Full article

The present work describes the facile synthesis of 3-(phenylethynyl)-7H-benzo[de]anthracen-7-one via a Sonogashira coupling reaction. The structure of the synthesized benzanthrone derivative is characterized by ¹H- and ¹³C-NMR spectroscopy and high-resolution mass spectrometry. The photophysical properties of the title compound are investigated by means of UV-Vis and fluorescence spectroscopy in various organic solvents. Full article

We report a synthesis of 3-bromo-9-N′-(N,N-dimethylformamidino)benzanthrone in good yield by a condensation reaction of 3-bromo-9-aminobenzanthrone with dimethylformamide in the presence of phosphorous oxychloride. The structure of the synthesized amidine was characterized by FTIR-ATR, NMR experiments, and elemental analysis. The title compound was analyzed by UV-Vis and fluorescence spectroscopy in various organic solvents. Full article

New substituted azomethines of benzanthrone with heterocyclic substituents were synthesized by condensation reaction of 3-aminobenzo[de]anthracen-7-one with appropriate aromatic aldehydes. The resulting imines were reduced with sodium borohydride to the corresponding amines, the luminescence of which is more pronounced in comparison with the initial azomethines. The novel benzanthrone derivatives were characterized by NMR, IR, MS, UV/Vis, and fluorescence spectroscopy. The structure of three dyes was studied by the X-ray single crystal structure analysis. The solvent effect on photophysical behaviors of synthesized imines and amines was investigated. The obtained compounds absorb at 420–525 nm, have relatively large Stokes shifts (up to 150 nm in ethanol), and emit at 500–660 nm. The results testify that emission of the studied compounds is sensitive to the solvent polarity, exhibiting negative fluorosolvatochromism for the synthesized azomethines and positive fluorosolvatochromism for the obtained amines. The results obtained indicate that the synthesized compounds are promising as luminescent dyes. Full article

Luminescent derivatives of benzanthrone are becoming more useful based on their light-absorbing and fluorescent-emitting properties. Our previous studies showed that luminescent staining properties of the same benzanthrone dye differ for variable parasite samples. Therefore, two types of benzanthrone dyes were prepared. One has a strongly basic amidine group and a halogen atom, and the other has an amide moiety and a tertiary amine group. Trematoda Parafasciolopsis fasciolaemorpha is a liver fluke of a moose (Alces alces) and has a significant influence on the health and abundance of the moose population. Staining protocols for parasite P. fasciolaemorpha specific organ or organ systems imaging are mostly time-consuming and labor-intensive. The study aimed to compare the fixation technique and the staining protocol by synthesized benzanthrone luminescent dyes to determine detailed morphology, anatomical arrangement of the organ systems and gross organization of the muscle layers of P. fasciolaemorpha using confocal laser scanning microscopy. Luminophores were tested for samples fixed in different fixatives. Developed dyes and staining protocol resulting in imaging of all parts of trematode without additional sample preparation procedures, which usually are required for parasite examination. Obtained results confirmed that the most qualitative results could be reached using 3-N-(2-piperidinylacetamido)benzanthrone dye which has amide moiety and a tertiary amine group. Based on obtained results, 3-N-(2-piperidinylacetamido)benzanthrone gave more qualitative parasite visualization than 2-bromo-3-N-(N′,N′-dimethylformamidino)benzanthrone. Full article

A new fluorescent Zn(II) complex of symmetrical tripod form based on a 3-substituted benzanthrone (BT) has been synthesized and characterised. The basic photophysical properties of the new metal complex have been determined. It has been found by fluorescence spectroscopy that, one zinc ion forms a complex with the tripod ligand. The surface morphology of the ligand and its Zn(II) complex has been investigated by the scanning electron microscopy (SEM) technique. X-ray photoelectron spectroscopy (XPS) has been used for the characterisation of the chemical composition of the complex surfaces. The antibacterial activity of the Zn(II) complex has been investigated in solution and upon its deposition onto a cotton fabric. A reduction of biofilm formation on the surface of the cotton fabric has been observed compared to the non-treated cotton material. The results obtained demonstrate that the studied Zn(II) complex possesses good antimicrobial activity being most effective against the used Gram-positive bacteria. Full article