Synthesis, photophysical and electrochemical properties of novel 6,12-di(thiophen-2-yl) substituted indolo[3,2-b]carbazoles

Иргашев, Роман А.; Teslenko, Anton Yu.; Zhilina, Ekaterina F.; Schepochkin, Aleksandr V.; Eltsov, Oleg S.; Rusinov, Gennady L.; Charushin, Valery N.

doi:10.1016/j.tet.2014.04.093

Cited by 28 publications

(21 citation statements)

References 31 publications

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“…To synthesize 5 a , its precursor ( 6 a ; Scheme ) was prepared following the reported procedure . To synthesize 5 b , c , the corresponding substituted dihydroindolo[3,2‐ b ]carbazoles ( 6 b , c ) were synthesized from the known brominated dihydroindolo[3,2‐ b ]carbazoles 7 and 8 by Pd‐catalyzed coupling reactions (Scheme ). Finally, oxidation of 6 a – c with PbO 2 resulted in 5 a – c , respectively, in fair yields.…”

Section: Resultsmentioning

confidence: 99%

Revisiting Indolo[3,2‐b]carbazole: Synthesis, Structures, Properties, and Applications

2020

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Indolo[3,2‐b]carbazole presents a π‐skeleton with a remarkable electronic structure and interesting potential applications. It is, however, also associated with ambiguity and controversy. Herein, new derivatives of indolo[3,2‐b]carbazole are reported and they have enabled a comprehensive study on the electronic structure of indolo[3,2‐b]carbazole and the development of a new n‐type organic semiconductor. Experimental and computational studies show that indolo[3,2‐b]carbazole has a largely localized p‐benzoquinonediimine moiety and significant antiaromaticity. When substituted with (4‐silylethynyl)phenyl groups, the indolo[3,2‐b]carbazole exhibits one‐dimensional π–π stacking and functions as an n‐type organic semiconductor in solution‐processed field effect transistors.

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Section: Resultsmentioning

confidence: 99%

Revisiting Indolo[3,2‐b]carbazole: Synthesis, Structures, Properties, and Applications

2020

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“…[4] To synthesize 5a,i ts precursor (6a;Scheme 1) was prepared following the reported procedure. [16] To synthesize 5b,c,t he corresponding substituted dihydroindolo[3,2-b]carbazoles (6b,c)w ere synthesized from the known brominated dihydroindolo[3,2-b]carbazoles 7 [17] and 8 [18,19] by Pd-catalyzed coupling reactions (Scheme 1). Finally,o xidation of 6a-c with PbO 2 resulted in 5a-c,respectively,inf air yields.…”

Section: Resultsmentioning

confidence: 99%

Revisiting Indolo[3,2‐b]carbazole: Synthesis, Structures, Properties, and Applications

2020

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Indolo[3,carbazole presents a p-skeleton with ar emarkable electronic structure and interesting potential applications.Itis, however,also associated with ambiguity and controversy.Herein, new derivatives of indolo [3,2-b]carbazole are reported and they have enabled acomprehensive study on the electronic structure of indolo[3,2-b]carbazole and the development of an ew n-type organic semiconductor.E xperimental and computational studies show that indolo[3,2b]carbazole has al argely localized p-benzoquinonediimine moiety and significant antiaromaticity.W hen substituted with (4-silylethynyl)phenyl groups,t he indolo[3,2-b]carbazole exhibits one-dimensional p-p stacking and functions as an n-type organic semiconductor in solution-processed field effect transistors. Figure 1. a) Indolo[3,2-b]carbazole (1), 5,11-dihydroindolo[3,2-b]carbazole (2), and indeno[1,2-b]fluorene (3). b) Resonance structures of 1 with Clar's aromatic sextets highlighted in light blue. c) Substituted indolo[3,2-b]carbazoles.Figure 6. Output I-V curves for the best-performing OFET of 5c on CDPA-modified Al 2 O 3 measured under vacuum. Angewandte Chemie Forschungsartikel 9769

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“…It has previously been shown that π-excessive system of 6,12-disubstituted indolo[3,2- b ]carbazoles 1 has a high affinity to electrophilic agents, which react readily with these aromatic substrates, thus affording C2,8-substitution products (Fig. 2) [42–43]. …”

Section: Resultsmentioning

confidence: 99%

“…Taking into account the electron-donating character of the ICZ system, there is no doubt that electrophilic aromatic substitution (S E Ar) reactions are the most attractive chemical methods for modification of ICZ derivatives. We have recently reported several synthetic procedures for regioselective C2,8-formylation and acylation of indolo[3,2- b ]carbazoles, bearing electron-rich aromatic or heteroaromatic substituents at C-6 and C-12, and also demonstrated the usage of the obtained 2,8-bis(RCO)-substituted derivatives as building blocks for the synthesis of more complicated ICZ-containing compounds [42–44]. In addition, other research groups have previously reported convenient methods for C12-formylation, azo-coupling, bromination and chlorination of 6-mono-substituted ICZs [37], as well as C2- and C2,8-bromination of 6,12-disubstituted ICZs [23,38].…”

Section: Introductionmentioning

confidence: 99%

Nitration of 5,11-dihydroindolo[3,2-b]carbazoles and synthetic applications of their nitro-substituted derivatives

Иргашев¹,

Kazin²,

Rusinov³

et al. 2017

Beilstein J. Org. Chem.

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A new general approach to double nitration of 6,12-di(hetero)aryl-substituted and 6,12-unsubstituted 5,11-dialkyl-5,11-dihydroindolo[3,2-b]carbazoles by acetyl nitrate has been developed to obtain their 2,8-dinitro and 6,12-dinitro derivatives, respectively. A formation of mono-nitro derivatives (at C-2 or C-6) from the same indolo[3,2-b]carbazoles has also been observed in several cases. Reduction of 2-nitro and 2,8-dinitro derivatives with zinc powder and hydrochloric acid has afforded 2-amino- and 2,8-diamino-substituted indolo[3,2-b]carbazoles, while reduction of 6,12-dinitro derivatives under similar reaction conditions has been accompanied by denitrohydrogenation of the latter compounds into 6,12-unsubstituted indolo[3,2-b]carbazoles. Formylation of 6,12-dinitro derivatives has proved to occur only at C-2, while bromination of these compounds has taken place at both C-2 and C-8 of indolo[3,2-b]carbazole scaffold. Moreover, 6,12-dinitro-substituted indolo[3,2-b]carbazoles have been modified by the reactions with S- and N-nucleophiles. Notably, the treatment of 6,12-dinitro compounds with potassium thiolates has resulted in the displacement of both nitro groups, unlike potassium salts of indole or carbazole, which have caused substitution of only one nitro group.

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Synthesis, photophysical and electrochemical properties of novel 6,12-di(thiophen-2-yl) substituted indolo[3,2-b]carbazoles

Cited by 28 publications

References 31 publications

Revisiting Indolo[3,2‐b]carbazole: Synthesis, Structures, Properties, and Applications

Revisiting Indolo[3,2‐b]carbazole: Synthesis, Structures, Properties, and Applications

Revisiting Indolo[3,2‐b]carbazole: Synthesis, Structures, Properties, and Applications

Nitration of 5,11-dihydroindolo[3,2-b]carbazoles and synthetic applications of their nitro-substituted derivatives

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