“…It is worth noting that we have recently synthesized bis-triazines 6 and 7 from 5,6-diphenyl-1,2,4-triazine-3(2 H )-thione 8 . Their absorption and excited-emission spectra, as well as molecular structure optimization using the B3LYP/6–31G(d) level of theory, were investigated (Scheme 3 ) 14 . Scheme 3 Synthesis of compounds 6 and 7 .…”
Section: Resultsmentioning
confidence: 99%
“…The reaction mixture was heated at reflux for 1 h, then allowed to cool to room temperature. The formed crude solid was filtered off, dried in a vacuum oven, and recrystallized using dimethylformamide (DMF) giving yellow crystals of 3 and 5 , respectively 14 .…”
Section: Methodsmentioning
confidence: 99%
“…Spectroscopic methods and the density functional theory (DFT) have recently been used to identify the structures of a range of organic molecules 12 , 13 . In previous work 14 , we synthesized various bis-triazines with various spacers as chromophores. DFT and the time-dependent density functional theory (TD-DFT) studies confirmed that the spacer had a significant effect on their highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy gaps and other simulated characterizations.…”
Controlling photophysical properties is critical for the continued development of electroluminescent devices and luminescent materials. The preparation and study of novel molecules suitable as luminescent for the development of optoelectrical devices have recently received a lot of attention. Even though the as-triazine unit is a good building block for organic active substances, it is rarely used in this context. We created here novel bis-triazine derivative dyes in the far UV–Vis range by alkylation of triazine-thione derivatives with appropriate dibromo compounds. At the B3LYP/6-311**G(d,p) basis set, their optimal molecular structures were obtained. DFT technique confirmed that the new triazine derivatives are in noncoplanar with one of the two phenyl rings and the triazine plane rotating out by 102.09. Also, depending on the energy gap difference between HOMO and LUMO, some important parameters including chemical potential (π), electronegativity (χ), and chemical hardness (η) were calculated. The compounds may be readily polarized and have significant NLO characteristics, as seen by the tiny HOMO–LUMO energy gap. The calculated values for the polarizability (α) of the two new triazine derivatives have the range 6.09–10.75 × 10–24 (esu). The emission peaks seemed to move to the long-wavelength (redshift), with a rise in the fluorescence band, suggesting that the singlet excited state is more polar than the ground state. The influence of solvent polarity and the intermolecular charge transfer (ICT) processes are reflected in the photophysical properties of new fused triazine derivatives. These properties such as extinction coefficient, absorption and emission cross-sections, fluorescence quantum yield, fluorescence lifetime, oscillator strength, the dipole moment, radiative decay rate constant, the energy yield of fluorescence, and the attenuation length were assessed and discussed.
“…It is worth noting that we have recently synthesized bis-triazines 6 and 7 from 5,6-diphenyl-1,2,4-triazine-3(2 H )-thione 8 . Their absorption and excited-emission spectra, as well as molecular structure optimization using the B3LYP/6–31G(d) level of theory, were investigated (Scheme 3 ) 14 . Scheme 3 Synthesis of compounds 6 and 7 .…”
Section: Resultsmentioning
confidence: 99%
“…The reaction mixture was heated at reflux for 1 h, then allowed to cool to room temperature. The formed crude solid was filtered off, dried in a vacuum oven, and recrystallized using dimethylformamide (DMF) giving yellow crystals of 3 and 5 , respectively 14 .…”
Section: Methodsmentioning
confidence: 99%
“…Spectroscopic methods and the density functional theory (DFT) have recently been used to identify the structures of a range of organic molecules 12 , 13 . In previous work 14 , we synthesized various bis-triazines with various spacers as chromophores. DFT and the time-dependent density functional theory (TD-DFT) studies confirmed that the spacer had a significant effect on their highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy gaps and other simulated characterizations.…”
Controlling photophysical properties is critical for the continued development of electroluminescent devices and luminescent materials. The preparation and study of novel molecules suitable as luminescent for the development of optoelectrical devices have recently received a lot of attention. Even though the as-triazine unit is a good building block for organic active substances, it is rarely used in this context. We created here novel bis-triazine derivative dyes in the far UV–Vis range by alkylation of triazine-thione derivatives with appropriate dibromo compounds. At the B3LYP/6-311**G(d,p) basis set, their optimal molecular structures were obtained. DFT technique confirmed that the new triazine derivatives are in noncoplanar with one of the two phenyl rings and the triazine plane rotating out by 102.09. Also, depending on the energy gap difference between HOMO and LUMO, some important parameters including chemical potential (π), electronegativity (χ), and chemical hardness (η) were calculated. The compounds may be readily polarized and have significant NLO characteristics, as seen by the tiny HOMO–LUMO energy gap. The calculated values for the polarizability (α) of the two new triazine derivatives have the range 6.09–10.75 × 10–24 (esu). The emission peaks seemed to move to the long-wavelength (redshift), with a rise in the fluorescence band, suggesting that the singlet excited state is more polar than the ground state. The influence of solvent polarity and the intermolecular charge transfer (ICT) processes are reflected in the photophysical properties of new fused triazine derivatives. These properties such as extinction coefficient, absorption and emission cross-sections, fluorescence quantum yield, fluorescence lifetime, oscillator strength, the dipole moment, radiative decay rate constant, the energy yield of fluorescence, and the attenuation length were assessed and discussed.
“…However, 1,2,4-triazines possessing specific photophysical properties have seldom been used in optoelectrical research. Only a few 1,2,4-triazine derivatives have been employed as building blocks for organic photoactive materials, particularly organic light-emitting diodes [ 12 , 13 , 14 , 15 , 16 , 17 , 18 ]. However, their closed nitrogen congeners (such as triazoles, pyrimidines, and s -triazines) are an inexhaustible source of numerous photoactive substances for various applications in optoelectronics and luminescent materials [ 19 , 20 , 21 , 22 , 23 ].…”
New fluorescent dyes containing an assembled 1,4-dihydroazolo[5,1-c][1,2,4]triazine (DAT) core and an isoxazole ring were synthesized through a reaction between diazopyrazole or diazoimidazoles and isoxazolyl-derived enamines in mild conditions. The photophysical characteristics (maxima absorption and emission, Stokes shifts, fluorescent quantum yields, and fluorescence lifetimes) of the new fluorophores were obtained. The prepared DATs demonstrated emission maxima ranging within 433–487 nm, quantum yields within 6.1–33.3%, and a large Stokes shift. The photophysical characteristics of representative DAT examples were studied in ten different solvents. Specific (hydrogen bonds) and non-specific (dipole–dipole) intermolecular and intramolecular interactions were analyzed using XRD data and spectral experiments. Solvatochromism was analyzed using Lippert–Mataga and Dimroth–Reichardt plots, revealing the relationship between the DAT structure and the nature of solute–solvent interactions. The significant advantages of DATs are the fluorescence of their powders (QY up to 98.7%). DAT-NMe2 10 expressed bright aggregation-induced emission (AIE) behavior in DMSO and THF as the water content increased. The numerous possible variations of the structures of the heterocycles included in the DATs, as well as substituents, create excellent prospects for adjusting their photophysical and physicochemical properties.
“…Electronic devices based on organic compounds are at the head of current scientific research, with the goal of producing more environmentally efficient electronic devices. Organic materials can attain this, as they characteristically produce materials 2 of 19 that are less toxic and less solution-processable than their inorganic counterparts [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. Electrochromic organic molecules have distinctive color-altering properties after passing an electrical current, making them extremely suitable for colored displays and smart windows [15][16][17].…”
A novel 5-(5-Bromo-2-hydroxybenzylidene)-6-oxo-3-phenyl-5,6-dihydro-1,2,4-triazine-2(1H)-carbothioamide (4) “compound 4” was synthesized. The chemical structure of compound 4 was confirmed with spectroscopic techniques. Thermal analysis (TGA/dTGA) studies were conducted for identifying the kinetic thermodynamic parameters and the thermal stability of the synthesized compound 4. Cyclic voltammetric studies were performed for recognizing electrochemical characteristics of the synthesized compound 4. The calculated highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), and the band gap were found to be −3.61, −5.32, and 1.97 eV, respectively. Using a diffused reflectance spectroscopy (DRS) technique, the estimated values of the optical band transitions of compound 4 in powder form were found to be 2.07 and 2.67 eV. The structural properties of thermally evaporated compound 4 thin films were analyzed using field emission scanning electron microscopy (FESEM), X-ray diffraction (XRD), and Fourier transform infrared (FTIR) spectroscopy. It was found that compound 4 has a triclinic crystal structure. The optical transitions and the optical dispersion factors of compound 4 thin films were investigated using a UV-Vis spectroscopy technique. From the UV-Vis spectroscopy technique, Egind=3.6 V was estimated for both the as-deposited and annealed thin films. For the as-deposited film, there were two photoluminescence (PL) emission peaks centered at 473 and 490 nm with a shoulder at 422 nm. For the annealed film at 423 K, there were five PL emission peaks centered at 274, 416, 439, 464, and 707 nm with a shoulder at 548 nm. The dark electrical conduction of compound 4 thin film was through a thermally activated process with activation energy equaling 0.88 eV.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
