C 75 Consecutive S-N(H) and Suzuki–Miyaura Cross-Coupling Reactions – an Efficient Synthetic Strategy to Pyrimidines Bearing Pyrrole and Indole Fragments / E. V. Verbitskiy, G. L. Rusinov, V. N. Charushin, O. N. Chupakhin, E. M. Cheprakova, P. A. Slepukhin, M. G. Pervova, M. I. Kodess // European Journal of Organic Chemistry. - 2012. - Vol. 2012, №33. - С. 6612-6621 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHETIC METHODS -- CROSS-COUPLING -- NITROGEN HETEROCYCLES Аннотация: The combination of the Suzuki–Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen reactions is a versatile tool for the syntheses of 4-(1R-pyrrol-2-yl)- and 4-(1R-indol-3-yl)-5-(hetero)aryl-substituted pyrimidines from commercially available 5-bromopyrimidine. The SNH [AE, (addition–elimination)] and SNH [AO, (addition–oxidation)] reactions of 5-bromopyrimidine with pyrroles and indoles were studied by gas chromatography–mass spectrometry. The structures of the intermediate σH adducts as well as the pyrrole-(hetero)arylpyrimidine and indole-(hetero)arylpyrimidine dyads were established for the first time by X-ray crystal structure analysis \\\\Expert2\\nbo\\European Journal of Organic Chemistry\\2012, p.6612.pdf |
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 |
A 10 A facile and convenient synthesis and photovoltaic characterization of novel thieno[2,3-b]indole dyes for dye-sensitized solar cells [Electronic resource] / R. A. Irgashev, A. A. Karmatsky, S. Kozyukhin, V. K. Ivanov, A. Sadovnikov, V. V. Kozik // Synthetic Metals. - 2015. - Vol. 199. - С. 152-158. - Bibliogr. : p. 158 (28 ref/) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): THIENO[2,3-b]INDOLE -- DYES -- THIOPHENE Аннотация: Two novel dyes IK-1,2 bearing the 8-alkyl-8H-thieno[2,3-b]indole unit as an electron-donating part of the push-pull system have been designed and prepared, as promising sensitizers for solar cells. The key steps of the synthesis involve the crotonic condensation of 1-alkylisatins with 2-acetylthiophene, followed by reduction of the C=C double bond and further cyclization through the Paal-Knorr reaction with the Lawesson reagent, thus leading to the formation of 2-(thien-2-yl) substituted thieno[2,3-b] indole derivatives. The optical and electrochemical properties of these dye's have been investigated by using spectrophotometry and cyclic voltammetry respectively, while their photovoltaic performance was evaluated by a device fabricatien study. The DSSCs based on IK-1 and IK-2 have demonstrated an efficiency of eta = 0.37% (FF = 73%) and eta = 0.7g% (FF = 69%) under 100 mW cm(-2) simulated AM 1.5G solar irradiation, respectively. \\\\expert2\\nbo\\Synthetic Mеtals\\2015, V.199, p. 152-158.pdf |
C 75 Construction of Heteroacenes with Fused Thiophene and Pyrrole Rings via the Fischer Indolization Reaction [Electronic resource] / R. A. Irgashev, A. A. Karmatsky, G. L. Rusinov, V. N. Charushin // Organic Letters. - 2016. - Vol. 18, № 4. - С. 804-807 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): FUSED THIOPHENE -- PYRROLE RINGS -- FISCHER INDOLIZATION REACTION Аннотация: A convenient approach to ladder-type 6H-benzo[4',5']thieno[2',3':4,5]thieno[3,2-b]indoles, e.g., I (X-rays single crystal structure shown), bearing various substituents in both terminal benzene rings has been developed. The protocol suggested for prepg. these N,S-heteroacenes is based on using easily available reagents, such as cinnamic acids and arylhydrazines, which can be involved in the Fischer indole synthesis, as the key step. A similar condensed system of 12H-benzo[4'',5'']thieno[2'',3'':4',5']thieno[2',3':4,5]thieno[3,2-b]indole, bearing six rings, has also been obtained. \\\\expert2\\nbo\\Organic Letters\\2016, v.18, N 4, p.804-807,pdf.pdf |
N 89 Novel push-pull thieno[2,3-b]indole-based dyes for efficient dye-sensitized solar cells (DSSCs) / R. A. Irgashev, A. A. Karmatsky, G. A. Kim, G. L. Rusinov, V. N. Charushin, A. A. Sadovnikov, V. K. Ivanov, S. A. Kozyukhin, V. V. Emets, V. A. Grinberg // Arkivoc. - 2017. - Vol. 4. - P34-50 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): DYE-SENSITIZED SOLAR CELLS -- ELECTRON-RICH HETEROCYCLES -- METAL-FREE DYES -- PHOTOVOLTAIC PROPERTIES -- PUSH-PULL STRUCTURE -- THIENO[2,3-B]INDOLE Аннотация: New metal-free sensitizers (IK 3-6), based on the thieno[2,3-b]indole ring system, bearing various aliphatic substituents at the nitrogen atom (electron-donating part), several thiophene units (π-bridge linker) and 2-cyanoacrylic acid (the electron-accepting and anchoring group) have been synthesized for application in dye-sensitized solar cells (DSSCs). The relationship between the IK dye structure and efficiency of the corresponding DSSC has been elucidated. Power conversion efficiency (PCE) up to 6.3% (short-circuit photocurrent density (JSC) 19.0 mA cm-2, open-circuit voltage (VOC) 0.59 V, and fill factor (FF) 56.4%) were obtained for the DSSC, based on 2-cyano-3-{5-[8-(2-ethylhexyl)-8H-thieno[2,3-b]indol-2-yl]thiophen-2-yl}acrylic acid (IK 3), which proved to be a highly synthetic available compound, under simulated AM 1.5 G irradiation (100 mW cm-2), thus indicating that thieno[2,3-b]indole-based organic dyes are perspective candidates for DSSCs. \\\\Expert2\\NBO\\ARKIVOC\\2017 v.4 p.34-50.pdf |
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. |
Benzo[ b]selenophene/thieno[3,2-b]indole-based n,s,se-heteroacenes for hole-transporting layers / M. S. Demina, N. A. Rasputin, R. A. Irgashev [и др.] // ACS omega. - 2020. - № 5. - С. 9377-9383 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Two series of new N,S,Se-heteroacenes, namely, 6H-benzo[4′,5′]selenopheno[2′,3′:4,5]thieno[3,2-b]indoles and 12H-benzo[4″,5″]selenopheno[2″,3″:4′,5′]thieno[2′,3′4,5]thieno[3,2-b]indoles, were successfully obtained using an effective strategy based on Fiesselmann thiophene and Fischer indole synthesis. The new molecules exhibit a large optical band gap (2.82 eV Egopt 3.23 eV) and their highest occupied molecular orbital (HOMO) energy formed by the plane Ï-core ranges between-5.2 and-5.6 eV, with the narrower optical band gap and lower HOMO level corresponding to selenated heteroacenes. In thin solid films of the heteroacenes, hole mobility measured using the conventional CELIV technique ranges between 10-5 and 10-4 cm2·V-1·s-1. All these make the proposed condensed-ring compounds a promising platform for the development of hole-transporting materials applicable in organic electronics. |
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 |