Triazines, Tetrazines, and Fused Ring Polyaza Systems

Hiebel, Marie‐Aude; Suzenet, Franck

doi:10.1016/b978-0-12-819962-6.00014-2

Cited by 9 publications

(14 citation statements)

References 158 publications

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“…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 ].…”

Section: Introductionmentioning

confidence: 99%

Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties

et al. 2023

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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.

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Section: Introductionmentioning

confidence: 99%

Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties

et al. 2023

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“…The presence of both electron substituents that donate (D) and accept (A) in a single molecule also exposes interesting spectral and optical characteristics owing to intramolecular charge transfer (ICT). The 1,2,4-triazine unit has been used as a building block for organic active materials, particularly organic light-emitting diodes 8 , 9 . In this regard, Xiang et al 10 demonstrated the potential of as-triazines as luminescent materials.…”

Section: Introductionmentioning

confidence: 99%

Experimental and theoretical studies of linear and non-linear optical properties of novel fused-triazine derivatives for advanced technological applications

Al-Shamiri

Sakr

Abdel‐Latif

et al. 2022

Sci Rep

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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.

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“…1,2,4,5-Tetrazine derivatives have been actively studied in recent years [ 19 – 22 ]. These compounds are attractive as high-energy materials [ 23 – 25 ], molecules with promising photophysical, electrochemical and coordination properties for use in sensors, OLEDs, semiconductor materials, etc.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines and investigation of their fungistatic activity

Korotina¹,

Толщина²,

Ишметова³

et al. 2022

Beilstein J. Org. Chem.

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A series of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines has been synthesized through oxidation reaction of the corresponding 3,6-disubstituted 1,2,4,5-tetrazines bearing amidine fragments. It is shown that the heterocyclic systems obtained can be modified easily at C(3) position in the reactions with aliphatic alcohols and amines. Also, the reactivity of [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines towards CH-active compounds has been studied. The obtained triazolo[1,5-b]annulated 1,2,4,5-tetrazines proved to be active in micromolar concentrations in vitro against filamentous anthropophilic and zooanthropophilic dermatophyte fungi (Trichophyton, Microsporum and Epidermofiton), which cause skin and its appendages (hair, nails) diseases.

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Triazines, Tetrazines, and Fused Ring Polyaza Systems

Cited by 9 publications

References 158 publications

Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties

Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties

Experimental and theoretical studies of linear and non-linear optical properties of novel fused-triazine derivatives for advanced technological applications

Synthesis of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines and investigation of their fungistatic activity

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