Synthesis, photophysical and electrochemical properties of novel 6,12-di(thiophen-2-yl) substituted indolo[3,2-b]carbazoles / Irgashev R.A., Teslenko A.Y., Zhilina E.F., Schepochkin A.V., El'Tsov O.S., Rusinov G.L., Charushin V.N. // Tetrahedron. - 2014. - V. 70, l. 31. - P. 4685-4696.

ISSN:
00404020
Type:
Article
Abstract:
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. © 2014 Elsevier Ltd. All rights reserved.
Author keywords:
Acylation; Indole; Indolo[3,2-b]carbazole; Luminescence; N-Heteroacenes; Thiophene
Index keywords:
carbazole derivative; carbene; ester; Lewis acid; mercury; nitrile; alkylation; article; bromination; carbon nuclear magnetic resonance; catalysis; chemical modification; crystal structure; dehydrogen
DOI:
10.1016/j.tet.2014.04.093
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Affiliations I. Postovsky Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, S. Kovalevskoy Str., 22, Ekaterinburg 620041, Russian Federation; Ural Federal University Named after the First President of Russia B.N. Yeltsin, Mira St. 19, Ekaterinburg 620002, Russian Federation
Author Keywords Acylation; Indole; Indolo[3,2-b]carbazole; Luminescence; N-Heteroacenes; Thiophene
Chemicals/CAS carbene, 2465-56-7; mercury, 14302-87-5, 7439-97-6
Funding Details 13-03-12434-ofi-m2, RFBR, Russian Foundation for Basic Research; 13-03-96049-r-ural-a, RFBR, Russian Foundation for Basic Research; 14-03-01017-A, RFBR, Russian Foundation for Basic Research
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Correspondence Address Irgashev, R.A.; I. Postovsky Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, S. Kovalevskoy Str., 22, Ekaterinburg 620041, Russian Federation; email: irgashev@ios.uran.ru
Publisher Elsevier Ltd
CODEN TETRA
Language of Original Document English
Abbreviated Source Title Tetrahedron
Source Scopus