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A Strategy towards the Multigram Synthesis of Uncommon Hexaarylbenzenes
Author(s) -
Lungerich Dominik,
Reger David,
Hölzel Helen,
Riedel René,
Martin Max M. J. C.,
Hampel Frank,
Jux Norbert
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201600841
Subject(s) - chemistry , electrophile , combinatorial chemistry , surface modification , cascade , organic synthesis , molecule , organic molecules , nanotechnology , organic chemistry , computational chemistry , catalysis , materials science , chromatography
A novel rational synthetic pathway—the “functionalization of para ‐nitroaniline” (FpNA)—provides substituted hexaarylbenzenes (HABs) with uncommon symmetries that bear up to five different substituents, fully avoiding regioisomeric product distributions during the reactions. 4‐Nitroaniline is functionalized by a cascade of electrophilic halogenations, Sandmeyer brominations, and Suzuki cross‐coupling reactions, leading to 26 substitution geometries, of which 18 structures are not available by the current established techniques. Furthermore, we demonstrate that this method is applicable to the bulk production of such systems on a multigram scale. Regarding optoelectronic properties, we demonstrate how highly functionalized HABs can show strong luminescent behavior, making these molecules very attractive to organic electronic devices.