S 98 Synthesis, photophysical and electrochemical properties of novel 6,12-di(thiophen-2-yl) substituted indolo[3,2-b]carbazoles [Electronic resource] / R. A. Irgashev, A. Yu. Teslenko, E. F. Zhilina, A. V. Schepochkin, O. S. Eltsov, G. L. Rusinov, V. N. Charushin // Tetrahedron. - 2014. - Vol.70, №31. - С. 4685-4696 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): INDOLO[3,2-B]CARBAZOLE -- INDOLE -- THIOPHENE Аннотация: Novel 5,11-dialkyl-6,12-di(thiophen-2-yl) substituted 5,11-dihydroindolo[3,2-b]carbazoles have been obtained and plausible ways for their further modifications via the Friedel–Crafts reaction are presented. The formylation of these indolo[3,2-b]carbazoles with dichloromethyl alkyl esters catalysed by Lewis acids leads to the formation of the corresponding 2,8-diformyl derivatives. Applicability of this formylation method for modification of indolo[3,2-b]carbazoles bearing electron-rich aromatic substituents at C-6 and C-12 has also been demonstrated. The Knoevenagel condensation of 2,8-dialdehydes with active methylene nitriles has been studied. The measurements of optical and redox properties for a number of new indolo[3,2-b]carbazoles have been performed \\\\expert2\\nbo\\Tetrahedron\\2014, v. 70 , p. 4685-4696.pdf |
5-(Methylidene)barbituric acid as a new anchor unit for dye-sensitized solar cells (DSSC) [Electronic resource] / R. A. Irgashev, G. A. Kim, G. L. Rusinov, V. N. Charushin // ARKIVOC. - 2014. - Vol. 2014, №5. - С. 123-131. - Bibliogr. : p. 131 (14 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ANCHOR GROUP -- BARBITURIC ACID -- CARBAZOLE Аннотация: Novel dyes bearing a 5-(methylidene)barbituric acid moiety as a new acceptor/anchor fragment were obtained and exhibited remarkable photophysical properties, according to a preliminary assessment of their sensitization activity as elements for dye-sensitized solar cells \\\\expert2\\nbo\\ARKIVOC\\2014, p.123-131.pdf |
S 98 Synthesis, Photophysical and Redox Properties of the D-pi-A Type Pyrimidine Dyes Bearing the 9-Phenyl-9H-Carbazole Moiety [Electronic resource] / E. V. Verbitskiy [и др.] // Journal of Fluorescence. - 2015. - Vol. 25, № 3. - С. 763-775. - Bibliogr. : p. 774-775 (51 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRIMIDINES -- CARBAZOLE -- DYE-SENSITIZED SOLAR CELLS Аннотация: Novel donor-pi-acceptor dyes bearing the pyrimidine unit as an electron-withdrawing group have been synthesized by using combination of two processes, based on the microwave-assisted Suzuki cross-coupling reaction and nucleophilic aromatic substitution of hydrogen. Spectral properties of the obtained dyes in six aprotic solvents of various polarities have been studied by ultraviolet-visible and fluorescence spectroscopy. In contrast to the absorption spectra, fluorescence emission spectra displayed a strong dependence from their solvent polarities. The nature of the observed long wavelength maxima has been elucidated by means of quantum chemical calculations. The electrochemical properties of these dyes have been investigated by using cyclic voltammetry, while their photovoltaic performance was evaluated by a device fabrication study. The experimental and calculation data show that all of the dyes can be regarded as potentially good photosensitizers for dye-sensitized solar cells. \\\\expert2\\nbo\\Journal of Fluorescence\\2015, v.25, p.763-775.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 \\\\expert2\\NBO\\Tetrahedron\\2016, v. 72 , p. 4954-4961.pdf |
A 10 A new synthetic approach to fused nine-ring systems of the indolo[3,2-b] carbazole family through double Pd-catalyzed intramolecular C-H arylation [Electronic resource] / R. A. Irgashev, N. A. Kazin, G. A. Kim, G. L. Rusinov, V. N. Charushin // RSC Advances. - 2016. - Vol. 6, № 74. - С. 70106-70116 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): IGHT-EMITTING-DIODES -- BIPOLAR HOST MATERIALS -- HOLE-TRANSPORTING MATERIALS Аннотация: A series of new polycyclic compounds bearing the 5,11-dihydroindolo[3,2-b] carbazole ring system, as the common motif of their nine-ring scaffolds, has been successfully prepared with the usage of an efficient two-step strategy, based on the double Friedel-Crafts acylation of 5,11-dihexyl-6,12-di(hetero) aryl-substituted 5,11-dihydroindolo[3,2-b] carbazoles with 2-iodobenzoyl chloride in the presence of SnCl4, followed by regioselective palladium-catalyzed cyclization of the obtained 2,8-bis(2-iodobenzoyl) derivatives into the desired fused 9H-fluoren-9-ones. Some modifications of these nine-ring structures have been performed to afford compounds of the same family bearing the 9H-fluorene fragments. Basic photophysical and electrochemical properties as well as thermal stability of the new fused indolo[3,2-b] carbazole derivatives have been determined. \\\\expert2\\NBO\\RSC Advances\\2016. Vol. 6, N 74. P. 70106.pdf |
A 10 A new synthetic approach to fused nine-ring systems of the indolo[3,2-b]carbazole family through double Pd-catalyzed intramolecular C–H arylation / R. A. Irgashev, N. A. Kazin, G. A. Kim, G. L. Rusinov, V. N. Charushin // RSC Advances. - 2016. - Vol. 6. - С. 70106-70116. - Bibliogr. : p. 70115-70116 (22 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): Pd-CATALYZED -- C–H ARYLATION -- SYNTHESIS \\\\expert2\\NBO\\RSC Advances\\2016. Vol. 6, N 70106.pdf |
A 10 A convenient synthesis of new 5,11-dihydroindolo[3,2-b]carbazoles bearing thiophene, 2,2′-bithiophene or 2,2′:5′,2″-terthiophene units at C-2 and C-8 positions / R. A. Irgashev, N. A. Kazin, G. L. Rusinov, V. N. Charushin // Tetrahedron Letters. - 2017. - Vol. 58, № 32. - P3139-3142 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 5,11-DIHYDROINDOLO[3,2-B]CARBAZOLE -- THIOPHENE -- 3-CHLOROACRYLALDEHYDE -- THE VILSMEIER–HAACK FORMYLATION -- THE FIESSELMANN REACTION Аннотация: A series of new 5,11-dihydroindolo[3,2-b]carbazole derivatives, containing functional thiophene, 2,2′-bithiophene or 2,2′:5′,2″-terthiophene moieties at both C-2 and C-8 positions of their fused scaffolds, have been obtained from 2,8-diacetyl-substituted 5,11-dihydroindolo[3,2-b]carbazole compounds through the effective strategy, which is based on the sequence of two reactions, namely the Vilsmeier–Haack formylation and the Fiesselmann thiophene synthesis. The starting acetyl substituted materials have been transformed into the corresponding 3-chlorocrylaldehyde-containing compounds by treatment with POCl3-DMF complex, followed by the reaction with alkyl thioglycolates or α-mercaptoacetone in the presence of triethylamine to afford 2-carboalkoxythiophene- or 2-acetylthiophene-linked derivatives. 2-Acetylthiophene derivatives have further been involved into the same sequence of reactions to obtain 2,2′-bithiophene-, and 2,2′:5′,2″-terthiophene-linked 5,11-dihydroindolo[3,2-b]carbazole compounds. \\\\Expert2\\NBO\\Tetrahedron Letters\\2017 v.58 p.3139-3142.pdf |
S 98 Synthesis and properties of new π-conjugated imidazole/carbazole structures / R. A. Irgashev, N. A. Kazin, N. I. Makarova, I. V. Dorogan, V. V. Malov, A. R. Tameev, G. L. Rusinov, A. V. Metelitsa, V. I. Minkin, V. N. Charushin // Dyes and Pigments. - 2017. - Vol. 141. - P512-520 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): IMIDAZOLES -- CARBAZOLES -- ABSORPTION SPECTRA -- PHOTOLUMINESCENCE -- TDDFT CALCULATIONS -- CHARGE MOBILITY Аннотация: New 3-(1H-imidazol-2-yl)-9H-carbazoles and 6,6′-di(1H-imidazol-2-yl)-9H,9′H-3,3′-bicarbazoles have been prepared, starting from 9-ethyl-9H-carbazole-3-carbaldehyde or 9,9′-diethyl-9H,9′H-[3,3′-bicarbazole]-6,6′-dicarbaldehyde through their reactions with 4-methoxyaniline or 4-fluoroaniline, benzil or 2,2′-thenil [1,2-di(thien-2,2′-yl) glyoxal] and ammonium acetate on reflux in glacial acetic acid. The obtained compounds have been shown to demonstrate an effective fluorescence in the blue spectral region, exhibiting quantum yields in the range of 0.08–0.51, depending on their molecular structure and solvent polarity. The nature of the observed absorption spectra has been elucidated by the TDDFT calculations. |
New push-pull systems based on indolo[3,2-b]carbazole and 1,2,4,5-tetrazine: synthesis, photophysical, and charge transport properties / A. S. Steparuk, S. G. Tolshchina, N. A. Kazin [et al.] // Russian chemical bulletin. - 2021. - Vol. 70, № 6. - P1109-1117 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,2,4,5-TETRAZINES -- NUCLEOPHILIC SUBSTITUTION -- INDOLO[3,2-B]CARBAZOLE -- PUSH-PULL SYSTEMS Аннотация: 5,11-Dihydroindolo[3,2-b]carbazoles were for the first time modified with acceptor 1,2,4,5-tetrazine fragments. The photophysical and charge-transport properties of the synthesized donor-acceptor heterocyclic systems were studied. It was shown that the introduction of the 1,2,4,5-tetrazine moieties makes it possible to increase the hole and electron mobility by one and two orders of magnitude, respectively, as compared to analogous 5,11-dihydroindolo-[3,2-b]carbazole derivatives studied previously. |
Synthesis, crystal structures and properties of carbazolebased [6]helicenes fused with an azine ring / D. I. Tonkoglazova, A. V. Gulevskaya, O. I. Askalepova, K. A. Chistyakov // Beilstein journal of organic chemistry. - 2021. - Vol. 17. - P11-21 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZINE-FUSED HELICENES -- CARBAZOLE-BASED [6]HELICENES -- HELICAL STRUCTURES Аннотация: Novel carbazole-based [6]helicenes fused with an azine ring (pyridine, pyrazine or quinoxaline) have been prepared through a five-step synthetic sequence in good overall yields. Commercially available 2,3-dihaloazines were used as starting materials. To discern the effect of merging an azine moiety within a helical skeleton, the X-ray structures, UV–vis absorption and fluorescence spectra of the helicenes were investigated and compared to that of the parent carbazole-based [6]helicene (7H-phenanthro[3,4-c]carbazole). |