New 2 H -[1,2,3]triazolo[4,5- e ][1,2,4]triazolo[1,5- a ]pyrimidine derivatives as luminescent fluorophores for detection of nitroaromatic explosives

Verbitskiy, Egor V.; Gorbunov, Evgeny B.; Баранова, А. А.; Lugovik, Kseniya I.; Khokhlov, Konstantin O.; Cheprakova, Ekaterina M.; Кim, Grigory А.; Rusinov, Gennady L.; Чупахин, О. Н.; Charushin, Valery N.

doi:10.1016/j.tet.2016.06.071

Cited by 32 publications

(11 citation statements)

References 34 publications

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“…Scheme 37 Fluorescent push-pull pyrimidine systems obtained by combination of the metal-free S N H and Suzuki cross-coupling reactions Also, the Lewis acid mediated S N H reaction was applicable to the direct C-H functionalization of a wide range of azolo[1,5-a]pyrimidines [129][130][131] and triazolo[a]-annulated 8-azapurines. 132,133 The use of an intramolecular version of nucleophilic aromatic substitution of hydrogen (the S N H reaction) and Scholl cyclodehydrogenation for the synthesis of substituted dibenzo[f,h]quinazolines 84 was discussed in a 2017 review (Scheme 38). 134…”

Section: E V Verbitskiy Et Almentioning

confidence: 99%

Recent Advances in Direct C–H Functionalization of Pyrimidines

et al. 2017

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Data spanning the period 2000–2017 on the direct C–H functionalization of pyrimidines are collected and discussed in this review. This demonstrates the surge of interest and creativity that this field of chemistry has experienced during the last two decades. Plausible applications of highly functionalized pyrimidines are also discussed.1 Introduction2 Transition-Metal-Catalyzed C–H Functionalization of Pyrimidine Derivatives3 Transition-Metal-Free Direct C–H Functionalization of Pyrimidine Derivatives4 Deprotonative Metalation of Pyrimidine Derivatives5 Conclusions

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Section: E V Verbitskiy Et Almentioning

confidence: 99%

Recent Advances in Direct C–H Functionalization of Pyrimidines

et al. 2017

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“…Push-pull nitrogen heterocyclic systems have also been designed for fluorescence sensing of nitroaromatic explosives. [21][22][23] Although sensitivity to acids has been used primarily for sensing applications, [24][25][26][27] a more recent application concerns white light emission. The protonation of azaheterocyclic push-pull derivatives generally leads to emission quenching.…”

Section: Introductionmentioning

confidence: 99%

Effect of protonation on the photophysical properties of 4-substituted and 4,7-disubstituted quinazoline push-pull chromophores

et al. 2021

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White-light emission from single molecular systems has attracted a great deal of attention due to their advantages over multicomponent emitters. Azaheterocyclic push-pull derivatives have been demonstrated to be white emitters by combining neutral and protonated forms in the appropriate ratio, although limited cases of white-light emission have been reported from quinazoline derivatives. Herein, we describe a series of push-pull 4-substituted and 4,7-disubstituted quinazolines that show white photoluminescence both in solution and in the solid state. All of the materials were prepared by straightforward Suzuki-Miyaura crosscoupling reactions and the compounds exhibited remarkable emission solvatochromism. In some cases the presence of acid prompted the appearance of emission bands of complementary colors. Thus, multicolor photoluminescence, including white light, could be finely tuned by the controlled protonation of the electron-deficient quinazoline ring.

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“…For example, they have applications in light sensors for colorsensitive solar cells [7] and polarity sensors [8]. They are used for a diverse range of applications [9,10].…”

Section: Introductionmentioning

confidence: 99%

A binuclear Cd(II) complex containing bridging pyrimidine-based ligands

Hosseini

Mardani

Moeini

et al. 2020

Zeitschrift Für Naturforschung B

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In this work, a pyrimidine-based ligand, N′-(amino(pyrimidin-2-yl)methylene)pyrimidine-2-carbohydrazonamide hydrate (APPH · H2O), and its binuclear complex of cadmium, [Cd(μ-APPH)Br]2, 1, were prepared and identified by elemental analysis, FT-IR, 1H NMR spectroscopy as well as single-crystal X-ray diffraction. X-ray structure analysis of 1 revealed octahedrally coordinated cadmium centers with a CdN4Br2 environment containing two bridging APPH ligands; each APPH ligand acts as an N4-donor (N2-donor toward each cadmium atom) and forms two five-membered chelate rings that are approximately perpendicular to each other. In the network of 1, the N–H · · · Br hydrogen bonds form motifs such as ${\rm{R}}_{\rm{2}}^{\rm{2}}(12,{\rm{ }}14),{\rm{ R}}_{\rm{6}}^{\rm{6}}(24,{\rm{ }}26,{\rm{ }} \ldots ,{\rm{ }}46).$ The crystal network is further stabilized by π-π stacking interactions between pyrimidine rings. The optimized structures of the ligand and complex were investigated along with their charge distribution patterns by density functional theory and natural bond orbital analysis, respectively.

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New 2 H -[1,2,3]triazolo[4,5- e ][1,2,4]triazolo[1,5- a ]pyrimidine derivatives as luminescent fluorophores for detection of nitroaromatic explosives

Cited by 32 publications

References 34 publications

Recent Advances in Direct C–H Functionalization of Pyrimidines

Recent Advances in Direct C–H Functionalization of Pyrimidines

Effect of protonation on the photophysical properties of 4-substituted and 4,7-disubstituted quinazoline push-pull chromophores

A binuclear Cd(II) complex containing bridging pyrimidine-based ligands

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