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Promising Molecules for Optoelectronic Applications: Synthesis of 5,10‐Dihydrobenzo[ a ]indolo[2,3‐ c ]carbazoles by Scholl Reaction of 1,2‐Bis(indol‐2‐yl)benzenes
Author(s) -
Daniels Mathias,
de Jong Flip,
Kennes Koen,
Martín Cristina,
Hofkens Johan,
Van der Auweraer Mark,
Dehaen Wim
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800791
Subject(s) - chemistry , electrophilic aromatic substitution , electrophilic substitution , electrophile , combinatorial chemistry , molecule , palladium , coupling reaction , oxidative coupling of methane , catalysis , stereochemistry , medicinal chemistry , organic chemistry
Only a few straightforward procedures for the preparation of indolo[2,3‐ c ]carbazoles are known, despite promising features for material applications. Herein we present a convenient synthesis of 5,10‐dihydrobenzo[ a ]indolo[2,3‐ c ]carbazoles using an oxidative cyclization of 1,2‐bis(1 H ‐indol‐2‐yl)benzenes prepared from readily accessible starting materials. Functionalization through electrophilic aromatic substitution reactions and palladium‐catalyzed cross‐coupling reactions were investigated, which lead to the isolation of new functionalized 5,10‐dihydrobenzo[ a ]indolo[2,3‐ c ]carbazoles, whose steady state electronic spectroscopy has been examined.