New 4,5-di(hetero)arylpyrimidines as sensing elements for detection of nitroaromatic explosives in vapor phase

Verbitskiy, Egor V.; Баранова, А. А.; Lugovik, Kseniya I.; Khokhlov, Konstantin O.; Cheprakova, Ekaterina M.; Shafikov, Marsel Z.; Rusinov, Gennady L.; Чупахин, О. Н.; Charushin, Valery N.

doi:10.1016/j.dyepig.2016.10.039

Cited by 43 publications

(20 citation statements)

References 40 publications

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“…4,5‐Diarylpyrimidines (Figure ) can be obtained from commercially available 5‐bromopyrimidine by nucleophilic aromatic substitution of the hydrogen at C4 followed by Suzuki cross‐coupling reaction on the C5 position . In all cases the emission maxima are observed in the green region (λ em =500–557 nm) (Table ).…”

Section: Arylpyrimidinesmentioning

confidence: 99%

Photoluminescence Properties of Aryl‐, Arylvinyl‐, and Arylethynylpyrimidine Derivatives

2018

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The extraordinary richness of push-pull molecules that incorporate pyrimidine rings as electron-withdrawing moieties in their structure is illustrated in this review. Interest in these pextended systems has increased dramatically over the last two decades due to their fluorescence properties and potential applications in sensing and as luminescent materials. As many as 422 different molecules are presented in an effort to establish structure-property relationships, which are often difficult to elucidate.[a] Dr.

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Section: Arylpyrimidinesmentioning

confidence: 99%

Photoluminescence Properties of Aryl‐, Arylvinyl‐, and Arylethynylpyrimidine Derivatives

2018

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“…The value of Stern‐Volmer constants of quinoxalines 1 a – c and dibenzo[ f,h ]quinoxalines 7 a – c (Table ) are rather large (up to 57800 M −1 in THF) and are close to or exceed those for the early studied V‐shaped pyrimidine‐based chromophores with K SV up to 26627 M −1 in CH 3 CN . Stern‐Volmer constant values decrease in the order a → b → c for both 1 and 7 quinoxaline derivatives.…”

Section: Resultsmentioning

confidence: 68%

Synthesis and Photophysical Studies of Novel V‐Shaped 2,3‐Bis{5‐aryl‐2‐thienyl}(dibenzo[f,h])quinoxalines

et al. 2020

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A series of novel V‐shaped luminophores containing electron‐withdrawing dibenzo[f,h]quinoxaline core and arylthienyl donor fragments at positions 2 and 3 has been synthesized. The absorption spectra (UV/vis) were recorded in several solvents, whereas emission spectra were recorded in solutions and powders. The solvatochromism as well as halochromism of obtained compounds was also explored. Electronic‐structure calculations using quantum‐chemistry methods were performed to further analyse experimental results. All characteristics were compared with that of 2,3‐bis(arylthienyl)quinoxaline counterparts. The halochromic effect studies showed that upon gradual addition of trifluoroacetic acid (TFA) to the toluene solution of diethylaminophenyl‐substituted dibenzo[f,h]quinoxaline chromophore, absorption and emission changed. Observed band shifts were more distinct in the case of mentioned quinoxaline than for other derivatives. All of the (dibenzo[f,h])quinoxaline chromophores exhibited good sensitivity toward nitro‐containing explosives with high Stern‐Volmer constants up to 57800 M−1, these results are remarkable for such heterocyclic systems.

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“…In our opinion, the most reasonable explanation of this fact is a steric hindrances increase with an addition of substituents in benzene ring. The linear relationship for the Stern-Volmer plot (in the range of concentrations from 0 to 2×10 -6 M) (Figures S6 and S7 in Supporting Information) and similarity of structures with linear and V-shaped push-pull pyrimidines, 35,40 bearing triphenylamine and carbazole as electron-donating fragment, suggests a high role of static type interactions for the quenching process.…”

Section: Optical Properties and Fluorescence Quenching Studies In Acementioning

confidence: 99%

“…Such structures have been used as promising sensing materials for detection of a variety of nitroaromatics through fluorescence quenching. [33][34][35][36][37][38][39][40] As a part of our research studies on pyrimidine-based π-conjugated systems, we envisaged that mixed π-conjugated 4,6-bis[5-(heteroaryl)-thiophen-2-yl]-5-(4-tert-butylphenyl) pyrimidines, consisting of the electrondonating part, presented by triphenylamine, carbazole or pyrene fragments, and the electron-withdrawing pyrimidine unit, would be a new class of push-pull fluorophores with improved sensitivity towards nitroaromatic compounds. Indeed, we have been motivated to synthesize D-π-A-π-D conjugates 7a-c, in which electrondonating groups are attached to 4-and 6-positions of the pyrimidine ring via the thiophene spacer and 4-tertbutylphenyl substituent is incorporated at C-5 of pyrimidines.…”

Section: Introductionmentioning

confidence: 99%

New "turn-off" fluorescence sensors to detect vapors of nitro-explosives on the basis of 4,6-bis[5-(heteroaryl)thiophen-2-yl] substituted 5-(4-tert-butylphenyl)pyrimidines

Verbitskiy¹,

Баранова²,

Yakovleva³

et al. 2017

Arkivoc

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New D-π-A-π-D type dyes based on compounds of the pyrimidine family, bearing thiophene linkers, have been designed, synthesized and characterized. The fluorescence behavior of these fluorophores have been evaluated for fifteen nitro compounds. The detection limits for these fluorophores in relation to nitro explosives in acetonitrile solution proved to be in the range from 10 -1 to 10 -6 mol/L. The sensor prototypes for handheld sniffer «Nitroscan» (Plant «Promautomatika», Ekaterinburg, Russia), based on these fluorophores, have been fabricated and used, as illustrated by reversible and sensitive fast detection of nitrobenzene in vapor phase concentrations up to 0.06 ppm.

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New 4,5-di(hetero)arylpyrimidines as sensing elements for detection of nitroaromatic explosives in vapor phase

Cited by 43 publications

References 40 publications

Photoluminescence Properties of Aryl‐, Arylvinyl‐, and Arylethynylpyrimidine Derivatives

Photoluminescence Properties of Aryl‐, Arylvinyl‐, and Arylethynylpyrimidine Derivatives

Synthesis and Photophysical Studies of Novel V‐Shaped 2,3‐Bis{5‐aryl‐2‐thienyl}(dibenzo[f,h])quinoxalines

New "turn-off" fluorescence sensors to detect vapors of nitro-explosives on the basis of 4,6-bis[5-(heteroaryl)thiophen-2-yl] substituted 5-(4-tert-butylphenyl)pyrimidines

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