Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 18, Pages 5602-5605Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201600841
Keywords
C-C coupling; halogenation; luminescence; materials; synthetic methods
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Funding
- German Research Council (DFG) through the Collaborative Research Center [SFB 953]
- Graduate School Molecular Science (GSMS)
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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.
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