title: A Strategy towards the Multigram Synthesis of Uncommon Hexaarylbenzenes.
abstract: 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.
authors.affiliation: Department Chemie und Pharmazie & Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany.
authors.forename: Dominik
authors.initials: D
authors.lastname: Lungerich
authors.affiliation: Department Chemie und Pharmazie & Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany.
authors.forename: David
authors.initials: D
authors.lastname: Reger
authors.affiliation: Department Chemie und Pharmazie & Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany.
authors.forename: Helen
authors.initials: H
authors.lastname: Hölzel
authors.affiliation: Department Chemie und Pharmazie & Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany.
authors.forename: René
authors.initials: R
authors.lastname: Riedel
authors.affiliation: Department Chemie und Pharmazie & Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany.
authors.forename: Max M J C
authors.initials: MM
authors.lastname: Martin
authors.affiliation: Department Chemie und Pharmazie & Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany.
authors.forename: Frank
authors.initials: F
authors.lastname: Hampel
authors.affiliation: Department Chemie und Pharmazie & Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany. norbert.jux@fau.de.
authors.forename: Norbert
authors.identifier: 0000-0002-5673-8181
authors.initials: N
authors.lastname: Jux
keywords: C-C coupling; halogenation; luminescence; materials; synthetic methods