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1.
Инвентарный номер: нет.
   

   
    Polyaromatic hydrocarbon (PAH)-based aza-POPOPS: synthesis, photophysical studies, and nitroanalyte sensing abilities / M. S. I. Mohammed, I. S. Kovalev, N. V. Slovesnova [et al.] // International journal of molecular sciences. - 2023. - Vol. 24, № 12. - P10084
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
AZA-POPOPS -- CLICK REACTIONS -- CHEMOSENSORS
Аннотация: 1,4-Bis(5-phenyl-2-oxazolyl)benzene (POPOP) is a common scintillation fluorescent laser dye. In this manuscript, the synthesis of 2-Ar-5-(4-(4-Ar'-1H-1,2,3-triazol-1-yl)phenyl)-1,3,4-oxadiazoles (Ar, Ar' = Ph, naphtalenyl-2, pyrenyl-1, triphenilenyl-2), as PAH-based aza-analogues of POPOP, by means of Cu-catalyzed click reaction between 2-(4-azidophenyl)-5-Ar-1,3,4-oxadiazole and terminal ethynyl-substituted PAHs is reported. An investigation of the photophysical properties of the obtained products was carried out, and their sensory response to nitroanalytes was evaluated. In the case of pyrenyl-1-substituted aza-POPOP, dramatic fluorescence quenching by nitroanalytes was observed.

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2.
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    A BF3-mediated C–H/C–Li coupling of 1,3,7-triazapyrene with 2-thienyllithium in the design of push–pull fluorophores and chemosensors for nitroaromatics / I. A. Lavrinchenko, T. D. Moseev, M. V. Varaksin [et al.] // New Journal of Chemistry. - 2022. - Vol. 46, № 11. - P5121-5128
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Mono- and bis-2-thienyl-substituted 1,3,7-triazapyrenes have been synthesized for the first time via BF3-mediated C–H/C–Li coupling of 1,3,7-triazapyrene with 2-thienyllithium in 33 and 51% yields, respectively. The photophysical properties of these polycyclic azaaromatics have been studied, with emission in the range of 450–500 nm and fluorescence quantum yields of up to 99% in methanol solutions being revealed. The turn-off chemosensing properties of 2-thienyl-substituted 1,3,7-triazapyrenes for the selective detection of nitroaromatics have also been assessed; in particular, the quenching constants according to the Stern–Volmer model, the quenching sphere radius according to the Perrin model, the detection limit and the quenching efficiency have been determined. In particular, 6,8-bis-(thiopen-2-yl)-1,3,7-triazapyrene, characterized by 10 times the quenching constant and limit of detection (LOD) compared to the mono-substituted analog, can be considered as the most promising chemosensor for determining nitroaromatic compounds. DFT calculations confirm the presence of intramolecular charge transfer (ICT) effects in the case of the obtained fluorophores and clarify the quenching mechanism for nitroaromatics.

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3.
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    Abnormal push-pull benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidine fluorophores in planarized intramolecular charge transfer (PLICT) state: Synthesis, photophysical studies and theoretical calculations / O. S. Taniya, V. V. Fedotov, L. K. Sadieva [et al.] // Dyes and Pigments. - 2022. - Vol. 204. - Ст. 110405
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The combination of excellent luminescence with high solvent polarity effect and aggregation induced emission (AIE) is an ideal combination for creating fluorophores/probes with high microenvironmental sensitivity. However, many push-pull chromophores of the D−A type in common intramolecular charge transfer (ICT) state with a significant solvatochromic effect and AIE activity, have poor luminescent properties. Herein, to overcome this problem by using reactions of nucleophilic aromatic hydrogen substitution (SNH), we have designed a series of novel 4-heteroaryl-substituted 2-aryl-2H-benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidine fluorophores possessing a planarized intramolecular charge transfer (PLICT) state. All these fluorophores exhibited high luminescence quantum yields (up to 60%) and large Stokes shift values of up to 7459 cm−1. Among them, the fluorophore 4h was found to exhibit the most pronounced positive solvatochromic effect and the probe 4f exhibited the most pronounced aggregation induced emission characteristics. This AIE behavior was further confirmed by means of time-resolved fluorescence lifetime measurements as well as DFT-assisted geometry optimization studies. In the presence of trifluoroacetic acid (TFA) compound 4h exhibited a well-pronounced acidochromism via visible color change from yellow-green to orange which returned to the original yellow-green solution after the addition of triethylamine (TEA). The Stern-Volmer constant for the probe 4h towards TFA was 38 M−1. Finally, for the compounds 4f, g, h theoretical calculations in the ground and excited states in different solvents were carried out to confirm the PLICT process. Based on all above the herein reported PLICT fluorophores 4a-h can be successfully applied as biological probes and optical switches.

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4.
Инвентарный номер: нет.
   
   T 44

   
    The Rh(III)-catalysed C-H/N-H annulation of 2-thienyl- and 2-phenyl-quinazolin-4(3: H)-ones with diphenylacetylene / T. N. Moshkina, E. V. Nosova, G. N. Lipunova [et al.] // New Journal of Chemistry. - 2021. - Vol. 45, № 19. - P8456-8466
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A series of 4,5-diphenyl-7H-thieno[2′,3′:3,4]pyrido[2,1-b]quinazolin-7-ones was synthesized via the Rh(III)-catalyzed annulation of 2-thienylquinazolin-4(3H)-ones with diphenylacetylene. 2-Phenylquinazolin-4(3H)-one amide alcoholysis and double C–H functionalization proceeded under the same reaction conditions with the formation of 2,3,7,8-tetraphenyl-1H-benzo[d,e][1,8]-naphthyridine derivatives. All compounds possess fluorescence properties in MeCN and toluene solutions as well as in the solid state. The aggregation induced emission (AIE) properties and the ability to detect Fe3+ cations were evaluated.

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5.
Инвентарный номер: нет.
   
   A 10

   
    A new approach to 4-arylstyrenes: microwave-assisted synthesis and photophysical properties / M. Z. Eddin, M. G. Pervova, E. F. Zhilina [et al.] // Russian chemical bulletin. - 2021. - Vol. 70, № 11. - P2139-2144
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
STYRENE -- 4-VINYLBIPHENYL DERIVATIVES -- SUZUKi—MIYAURA CROSS-COUPLING -- FLUORESCENCE

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6.
Инвентарный номер: нет.
   

   
    Asymmetrically substituted 5,5′′-diaryl-2,2′:6′,2′′-terpyridines as efficient fluorescence “turn-on” probes for Zn2+ in food/cosmetic samples and human urine / O. V. Shabunina, E. S. Starnovskaya, Y. K. Shaitz [et al.] // Journal of photochemistry and photobiology A: Chemistry. - 2021. - Vol. 408. - P113101
Рубрики: ХИМИЧЕСКИЕ НАУКИ

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7.
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    Substituted 2-(2-hydroxyphenyl)–3H-quinazolin-4-ones and their difluoroboron complexes: Synthesis and photophysical properties / T. N. Moshkina, E. V. Nosova, V. N. Charushin [et al.] // Spectrochimica acta part A: molecular and biomolecular spectroscopy. - 2021. - Vol. 252. - P119497
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
ESIPT -- FLUORESCENCE -- O-LIGAND -- BF2-COMPLEX2-(2-HYDROXYPHENYL)–3H-QUINAZOLIN-4-ONES
Аннотация: 2-(2-Hydroxyphenyl)–3H-quinazolin-4-ones with diverse substituents at phenol ring and their six-membered difluoroboron complexes have been synthesized via few-stage approach. The photophysical properties of target compounds have been investigated in two solvents as well as in the solid state. The nature of substituents and substitution point in the phenol moiety of ligands and resulting BF2-complexes on the photophysical properties of dyes have been explored. The complex bearing two t-Bu groups proved to be the most emissive in solid state, whereas its 5-methoxy and 4-diethylamino counterparts possess strong emission in toluene solution. The dyes exhibited large Stokes shifts which was attributed to excited state intramolecular proton transfer (ESIPT). Additionally, fluorescence of quinazolinones in the mixture of THF/water was studied. All ligands demonstrated emission enhancement with increase of water fraction which was due to aggregation induced emission.

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8.
Инвентарный номер: нет.
   

   
    Pyrene-based lipophilic/biphilic chemosensors for the fluorescence "turn-off" detection of nitroanalytes in aqueous media / I. S. Kovalev, L. K. Sadieva, O. S. Taniya [и др.] // AIP Conference Proceedings. - 2021. - Vol. 2388, № 1. - Ст. 030015
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Two approaches towards “turn off” fluorescence detection of nitroanalytes (dinitro-ortho-cresol (DNOC), 2,4,6-trinitrotoluene (TNT) and Riamilovir (Triazavirin ®) are reported such as by tuning the chemosensors structure or by changing the environment. In both cases the great response was achieved with Stern-Volmer quenching constants (KSV) as high as 2.28–3.14 × 104 M−1 (for structure modification approach) and 4.67 × 105 M−1 (for changing of environment approach).

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9.
Инвентарный номер: нет.
   

   
    Bispyrenylalkane chemosensor for the naked-eye detection of nitro-explosives / I. S. Kovalev, L. K. Sadieva, O. S. Taniya [et al.] // Chimica Techno Acta. - 2021. - Vol. 8, № 2. - P20218209
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
DETECTION OF EXPLOSIVES IN AQUEOUS MEDIA -- CHEMICAL SENSORS -- FLUORESCENCE QUENCHING -- PYRENE-BASED FLUOROPHORES
Аннотация: Pyrene-based compounds have a great potential as fluorescent chemosensors for various analytes including common nitroexplosives, such as 2,4,6-trinitrotoluene (TNT). Compounds having two pyrene units in one molecule, such as bispyrenylalkanes, are able to form stable, bright emissive in a visual wavelength region excimers both in non-polar and polar environments. In this work we wish to report that in non-polar solvents the excimer has poor chemosensing properties while in aqueous solutions it provides significant “turn-off” fluorescence response to TNT in the subnanomolar concentrations.

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10.
Инвентарный номер: нет.
   

   
    Computer vision vs. spectrofluorometer-assisted detection of common nitro-explosive components with bola-type PAH-based chemosensors / I. S. Kovalev, L. K. Sadieva, O. S. Taniya [et al.] // RSC Advances. - 2021. - Vol. 11, № 42. - P25850-25857
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Computer vision (CV) algorithms are widely utilized in imaging processing for medical and personal electronics applications. In sensorics CV can provide a great potential to quantitate chemosensors' signals. Here we wish to describe a method for the CV-assisted spectrofluorometer-free detection of common nitro-explosive components, e.g. 2,4-dinitrotoluene (DNT) and 2,4,6-trinitrotoluene (TNT), by using polyaromatic hydrocarbon (PAH, PAH = 1-pyrenyl or 9-anthracenyl) – based bola-type chemosensors. The PAH components of these chemical bolas are able to form stable, bright emissive in a visual wavelength region excimers, which allows their use as extended matrices of the RGB colors after imaging and digital processing. In non-polar solvents, the excimers have poor chemosensing properties, while in aqueous solutions, due to the possible micellar formation, these excimers provide “turn-off” fluorescence detection of DNT and TNT in the sub-nanomolar concentrations. A combination of these PAH-based fluorescent chemosensors with the proposed CV-assisted algorithm offers a fast and convenient approach for on-site, real-time, multi-thread analyte detection without the use of fluorometers. Although we focus on the analysis of nitro-explosives, the presented method is a conceptual work describing a general use of CV for quantitative fluorescence detection of various analytes as a simpler alternative to spectrofluorometer-assisted methods.

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