S 98 Synthesis and optical properties of new photochromic systems based on 1,2-bis(2-methylbenzo[b]thien-3-yl) hexafluorocyclopentenes and 5,7-dihydro-1H-1,2,5,7,8-pentaaza-s-indacen-6-one or 1,7-dihydro-5-thia-1,2,7,8- tetraaza-s-indacen-6-one derivatives [Electronic resource] / M. M. Krayushkin, A. M. Bogacheva, A. N. Komogortsev, B. V. Lichitsky, A. A. Dudinov, K. S. Levchenko, O. I. Kobeleva, T. M. Valova, V. A. Barachevskii, V. N. Charushin // Journal of Sulfur Chemistry. - 2013. - Vol.34, №6. - С. 580-587. - Bibliogr. : p. 587 (15 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): BIS(BENZOTHIENYL)HEXAFLUOROCYCLOPENTENES -- FLUORESCENT DYES -- PHOTOCHROMES Аннотация: New photochromic molecules based on 1,2-bis(2-methylbenzo[b]thien-3-yl) hexafluorocyclopentenes and fluorescent 5,7-dihydro-1H-1,2,5,7,8-pentaaza-s- indacen-6-one or 1,7-dihydro-5-thia-1,2,7,8-tetraaza-s-indacen-6-one derivatives were synthesized via nucleophilic substitution. Photochromic properties of the compounds and composite mixtures of fluorophores and photochrome were investigated \\\\expert2\\nbo\\Journal of Sulfur Chemistry\\2013. V. 34, N 6. P. 580-587.pdf |
B 78 Boron(III) Complexes with N,N'- and N,O-Heterocyclic Ligands: Synthesis and Spectroscopic Properties [Electronic resource] / G. N. Lipunova, E. V. Nosova, V. N. Charushin, O. N. Chupakhin // Comments on Inorganic Chemistry. - 2016. - Vol. 2016. - С. 1153470 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PROPERTIES -- PREPARATION -- SYNTHETIC PREPARATION Аннотация: This review is focused on consideration of effects of the nature of N,N'- and N,O-bidentate ligands on the structure and optical properties of their B(III) complexes. It has been established that B(III) complexes with asym. N,N'- and N,O-bidentate ligands, such as ortho-hydroxyphenyl substituted azaheterocycles and heteryl-β-ketoimines, exhibit large Stokes shifts, enhanced intensity, and extended range for luminescence in solns. as well as in solid state, comparable with characteristics of the family of BODIPYs derivs. Complexes of some bidentate ligands can be considered as promising fluorophores for applications in biomedical imaging, electroluminescent, solar cell devices, and other fields. \\\\expert2\\nbo\\Comments on Inorganic Chemistry\\2016. P. 1153470.pdf |
D 47 Detection of nitroaromatic explosives by new D-π-A sensing fluorophores on the basis of the pyrimidine scaffold [Electronic resource] / E. V. Verbitskiy, A. A. Baranova, K. I. Ludovik, M. Z. Shafikov, K. O. Khokhlov, E. M. Cheprakova, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Analytical and Bioanalytical Chemistry. - 2016. - Ahead of Print Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NITROAROMATIC EXPLOSIVES -- PYRIMIDINE SCAFFOLD Аннотация: A series of D-π-A- type dyes based on pyrimidines, bearing various thiophene linkers, have been studied as sensing fluorophores. Fluorescence studies have demonstrated that the emission of all derivs. is sensitive to the presence of nitroarom. explosives, such as 2,4,6-trinitrophenol (PA), 2,4,6-trinitrotoluene (TNT), and 2,4-dinitrotoluene (DNT), in their acetonitrile solns. The detection limits of fluorophores to PA, TNT, and DNT proved to be in the range from 5.83 × 10-6 to 2.38 × 10-7 mol/L, 1.70 × 10-4 to 8.40 × 10-6 mol/L, and 8.39 × 10-5 to 6.87 × 10-6 mol/L, resp. The theor. investigation into the quenching mechanism in the presence of fluorophore has been performed. All compds. have shown a good efficiency as sensor materials when tested as elements of the original device < \\\\expert2\\nbo\\Analytical and Bioanalytical Chemistry\\2016, Ahead Print.pdf |
N 52 New 2H-[1,2,3]triazolo[4,5-e][1,2,4]triazolo[1,5-a]pyrimidine derivatives as luminescent fluorophores for detection of nitroaromatic explosives [Electronic resource] / E. V. Verbitskiy, E. B. Gorbunov, A. A. Baranova, K. I. Ludovik, K. O. Khokhlov, E. M. Cheprakova, G. A. Kim, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Tetrahedron. - 2016. - Vol. 72, № 32. - С. 4954-4961 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CARBAZOLE -- NITROAROMATIC EXPLOSIVES -- TRIPHENYLAMINE Аннотация: A number of D-pi-A type dyes on the basis of new 2H[1,2,3]triazolo[4,5-e][1,2,4]triazolo[1,5-a]pyrimidines, bearing various electron-donating carbazole and triphenylamine fragments, have been studied as sensing fluorophores. Fluorescence studies have demonstrated that emission spectra of these compounds in acetonitrile are sensitive to the presence of nitroaromatic explosives, such as 2,4-dinitroanisole (DNAN), picric acid (PA), styphnic acid (SA), 1,3,5-triethoxy-2,4,6-trinitrobenzene (TETNB), 2,4-dinitrotoluene (DNT), 2,4,6-trinitrotoluene (TNT) and nitrobenzene (NB). Detection limits of fluorophores for DNAN, PA, SA, TETNB, DNT and TNT proved to be in the range from 4.82x10(-1) to 2.96x10(-3) mol/L, 2.10x10(-3) to 5.98x10(-5) mol/L, 1.26x10(-1) to 2.02x10(-4) mol/L, 1.58 x 10(-1) to 1.62x10(-3) mol/L, 1.26x10(-1) to 5.61x10(-4) mol/L and 9.01x10(-2) to 2.77x10(-3) mol/L, respectively. Selective fluorescence quenching response, including a sharp color change under UV irradiation (especially for PA, SA and DNT), makes these compounds promising fluorescence chemosensors for nitroaromatic explosives \\\\expert2\\NBO\\Tetrahedron\\2016, v. 72 , p. 4954-4961.pdf |
N 52 New 4,5-di(hetero)arylpyrimidines as sensing elements for detection of nitroaromatic explosives in vapor phase / E. V. Verbitskiy, A. A. Baranova, K. I. Lugovik, K. O. Khokhlov, E. M. Cheprakova, M. Z. Shafikov, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Dyes and Pigments. - 2016. - Vol. 137. - С. 360-371. - Bibliogr. : p. 370-371 (50 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 4,5-DI(HETERO)ARYLPYRIMIDINES -- NITROAROMATIC EXPLOSIVES -- VAPOR PHASE Аннотация: A series of D–π–A–π–D type dyes based on pyrimidines, bearing thiophene linkers, have been studied as sensing fluorophores. Fluorescence studies have demonstrated that the emission of all derivatives is sensitive to the presence of 2,4,6-trinitrotoluene (TNT) and other nitroaromatic compounds (NACs), in their acetonitrile solutions. The detection limits of fluorophores to NACs proved to be in the range from 10−4 to 10−6 mol/L. The time-resolved fluorescence measurements and theoretical investigation into the quenching mechanism in the presence of fluorophore has been performed. The two types of sensor prototypes for handheld sniffer «Nitroscan» (Plant «Promautomatika», Ekaterinburg, Russia) on the basis of non-woven dry wipe and spunlace non-woven fabric with various quantities of the most sensitive fluorophore have been fabricated. The reusable, reversible and sensitive response of the designed prototypes to NACs enables one to qualify these compounds as promising fluorescent sensory materials for detection of NACs. \\\\expert2\\nbo\\Dyes and Pigments\\2016, v. 137, p.360-371.pdf |
N 52 New 4,5-di(hetero)arylpyrimidines as sensing elements for detection of nitroaromatic explosives in vapor phase / E. V. Verbitskiy, A. A. Baranova, K. I. Lugovik, K. O. Khokhlov, E. M. Cheprakova, M. Z. Shafikov, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Dyes and Pigments. - 2017. - Vol. 137. - P360-371 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): FLUORESCENCE QUENCHING -- NITROAROMATIC EXPLOSIVES -- TRIPHENYLAMINES -- CARBAZOLES -- PYRIMIDINES Аннотация: A series of D–π–A–π–D type dyes based on pyrimidines, bearing thiophene linkers, have been studied as sensing fluorophores. Fluorescence studies have demonstrated that the emission of all derivatives is sensitive to the presence of 2,4,6-trinitrotoluene (TNT) and other nitroaromatic compounds (NACs), in their acetonitrile solutions. The detection limits of fluorophores to NACs proved to be in the range from 10−4 to 10−6 mol/L. The time-resolved fluorescence measurements and theoretical investigation into the quenching mechanism in the presence of fluorophore has been performed. The two types of sensor prototypes for handheld sniffer «Nitroscan» (Plant «Promautomatika», Ekaterinburg, Russia) on the basis of non-woven dry wipe and spunlace non-woven fabric with various quantities of the most sensitive fluorophore have been fabricated. The reusable, reversible and sensitive response of the designed prototypes to NACs enables one to qualify these compounds as promising fluorescent sensory materials for detection of NACs. |
Synthesis and characterization of linear 1,4-diazine-triphenylamine–based selective chemosensors for recognition of nitroaromatic compounds and aliphatic amines / E. V. Verbitskiy, Y. A. Kvashnin, E. F. Zhilina [et al.] // Dyes and pigments. - 2020. - Vol. 178. - P108344 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ALIPHATIC AMINES -- FLUORESCENCE QUENCHING -- NITROAROMATIC COMPOUNDS -- PYRAZINE -- QUINOXALINE -- SOLVATOCHROMISM Аннотация: Novel 1,4-diazine-based dyes of the D–π–A type, possessing triphenylamine as an electron-donating group, have been developed. Fluorescence studies have demonstrated that emission of these fluorophores is sensitive towards different nitroaromatic compounds and aliphatic amines, both in solutions and in a vapor phase. Moreover, these compounds can be considered as “naked-eye” fluorescent probes for solution polarity because they possess pronounced solvatochromic properties. Therefore, these compounds have to be regarded as potential multifunctional chemosensors for monitoring hazardous organic substances. |
Aryne-mediated transformations of 5-perfluorophenyl-substituted 3-(pyridin-2-yl)-1,2,4-triazines in the design of novel 10-(1h-1,2,3-triazol-1-yl)pyrido[1,2-a]indole fluorophores / T. D. Moseev, M. V. Varaksin, I. A. Lavrinchenko [и др.] // Tetrahedron. - 2020. - Vol. 76, № 18. - P131147 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,2,3-TRIAZOLES -- ARYNE-MEDIATED TRANSFORMATIONS -- CAOSAMBHWGMFEW-UHFFFAOYSA-N -- CYFQLMLVDSTHGC-UHFFFAOYSA-N -- FLUOROARENES Аннотация: A number of novel fluorinated derivatives of the family of pyrido[1,2-a]indole fluorophores have first been synthesized via the aryne-mediated domino transformations of 5-(perfluorophenyl)-3-(pyridin-2-yl)-1,2,4-triazines. A comprehensive study of photophysical properties of the obtained polyfluoroaryl substituted derivatives, in which polyfluoroaryl, 1,2,3-triazole, and pyridoindole subunits contribute to a joint chromophore system, has shown that these compounds proved to exhibit a fluoresce with green light in acetonitrile solutions. |
Azaheterocyclic push-pull chromophores: synthesis, photophysical properties and applications as fluorescent sensors / E. V. Verbitskiy, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Actual problems of organic chemistry and biotechnology. - Екатеринбург, 2020. - P73-75 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIMIDINE -- PYRAZINE -- FLUORESCENCE QUENCHING -- PUSH-PULL FLUOROPHORES |
Photosphysical properties of green-emitting polyfluorinated 10-(1h-1,2,3-triazol-1-yl)pyrido[1,2-a]indole fluorophores / T. D. Moseev, M. V. Varaksin, D. A. Gorlov [et al.] // Actual problems of organic chemistry and biotechnology. - Екатеринбург, 2020. - P271-273 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIDO[1,2-A]INDOLES -- FLUOROPHORES |
Novel push-pull fluorophores based on polyfluoroaryl-modified 2H-imidazoles / T. D. Moseev, M. V. Varaksin, E. A. Virlova, V. N. Charushin, O. N. Chupakhin // Mendeleev 2021: book of abstracts XII international conference on chemistry for young scientists. - Saint Petersburg, 2021. - С. 606 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
Bola-type pah-based fluorophores/chemosensors: synthesis via an unusual clemmensen reduction and photophysical studies / I. S. Kovalev, L. K. Sadieva, O. S. Taniya [et al.] // Journal of photochemistry and photobiology A: Chemistry. - 2021. - Vol. 420. - P113466 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
A 99 Azapyrene-based fluorophores: synthesis and photophysical properties / O. S. Taniya, A. F. Khasanov, M. V. Varaksin [et al.] // New Journal of Chemistry. - 2021. - Vol. 45, № 45. - P20955-20971 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Azapyrenes are the nitrogen isosteres of pyrene. Based on theoretical and experimental studies, electron–acceptor azapyrene domains may be considered as convenient scaffolds for constructing a large variety of “push–pull” π-conjugated chromophores with pronounced ICT properties. Over the past decade, due to the unrelenting interest in functional materials and modern methodologies such as cross-coupling, peri-annulation, direct C–H-functionalization, etc., methods for the synthesis of aryl(alkyl) K-functionalized azapyrenes and other derivatives have been developed, and their photophysical and electrochemical properties have been studied. This short review aims at critical analysis of the best known/modern methods for the preparation of functionalized azapyrene derivatives, as well as an assessment of their photophysical/electrochemical properties in comparison with the structural and electronic properties of the parent pyrene. |
1,3,7-triazapyrene-based ortho-carborane fluorophores: convenient synthesis, theoretical studies, and aggregation-induced emission properties / L. A. Smyshliaeva, M. V. Varaksin, E. I. Fomina [et al.] // Organometallics. - 2021. - Vol. 40, № 16. - P2792-2807 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A convenient transition-metal-free approach, based on nucleophilic substitution of hydrogen (SNH), for consecutive regioselective C–H functionalization of 1,3,7-triazapyrene scaffolds with carboranyllithium and phenyllithium is reported. The theoretical calculations disclosed highlight key features in the regioselectivity and mechanism of the investigated SNH transformations. The novel 1,3,7-triazapyrene-based ortho-carboranes obtained have large potential in the field of molecular electronics as organic luminophores, which are characterized by the aggregation-induced emission and dual-emission effects. |
Novel pentafluorophenyl- and alkoxyphenyl-appended 2,2'-bipyridine push-pull fluorophores: a convenient synthesis and photophysical studies / T. D. Moseev, E. A. Nikiforov, M. V. Varaksin [et al.] // Synthesis. - 2021. - Vol. 53, № 19. - P3597-3607 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 2,2′-BIPYRIDINES -- 1,2,4-TRIAZINES -- POLYFLUOROARENES Аннотация: A convenient method for the synthesis of new highly in non-polar solvents soluble photoactive pentafluorophenyl-substituted and extended alkoxyphenyl-substituted 2,2′-bipyridines is reported. The synthetic strategy for the preparation of such ligands involves a sequence of several structural transformations, such as O-alkylation, nucleophilic substitution of hydrogen (SN H) in 1,2,4-triazine precursors via the ‘addition–elimination’ scheme, and the subsequent conversion of the obtained 1,2,4-triazines into 2,2′-bipyridines by means of the aza-Diels–Alder reaction. The photophysical properties of the synthesized novel pentafluoroaryl-substituted 2,2′-bipyridines were comprehensively studied. The obtained photophysical data indicate the competitive advantages of the herein reported pentafluoroarylated push–pull fluorophores, bearing extended aliphatic moieties, over their analogues containing benzoxy or phenolic fragments in terms of improvement in quantum yield and well-pronounced positive solvatochromism confirmed by the mathematical analysis according to the Lippert–Mataga equation. |
Meso-functionalization of calix[4]arene with 1,3,7-triazapyrene in the design of novel fluorophores with the dual target detection of Al3+ and Fe3+ cations / T. D. Moseev, I. A. Lavrinchenko, M. V. Varaksin [et al.] // RSC Advances. - 2021. - Vol. 11, № 11. - P6407-6414 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A meso-functionalization strategy has successfully been applied to the synthesis of novel 1,3,7-triazapyrene derivatives of calixarenes. The key synthetic step in these transformations providing the direct C–C bond formation is nucleophilic substitution of hydrogen (SNH) in 1,3,7-triazapyrene. General photophysical characteristics for these macrocyclic compounds, as well as features in emission properties upon addition of various metal cations have been elaborated. Studies using NMR spectroscopy have also shown a mutual effect of both calix[4]arene and 1,3,7-triazapyrene moieties on the coordination process. The complex stoichiometry and binding constants for Al3+ and Fe3+ guests have been explored with titration experiments. |
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. |
Synthesis of “push-pull” fluorophores based on 2-aryl(heteryl)quinazolines / T. N. Moshkina, A. E. Kopotilova, E. V. Nosova [et al.] // Mendeleev 2021: book of abstracts XII international conference on chemistry for young scientists. - Saint Petersburg, 2021. - P607 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
Synthesis of new water-soluble polyarene-substituted naphtho[1,2-d]oxazole-based fluorophores as fluorescent dyes and biological photosensitizers / N. V. Slovesnova, A. S. Minin, O. S. Taniya [et al.] // Dyes and Pigments. - 2022. - Vol. 204. - Ст. 110410 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
Fluoroaromatic 2H-imidazole-based push-pull fluorophores: Synthesis, theoretical studies, and application opportunities as probes for sensing the pH in saliva / T. D. Moseev, M. V. Varaksin, E. A. Virlova [et al.] // Dyes and Pigments. - 2022. - Vol. 202. - Ст. 110251 Рубрики: ХИМИЧЕСКИЕ НАУКИ |