Department Chemie und Pharmazie & Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany.
Angew Chem Int Ed Engl. 2016 Apr 25;55(18):5602-5. doi: 10.1002/anie.201600841. Epub 2016 Mar 24.
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.
一种新颖的合理合成途径——“对硝基苯胺的功能化”（FpNA）——为具有不常见对称性的取代六芳基苯（HAB）提供了五个不同取代基，在反应过程中完全避免了区域异构体产物分布。通过一系列亲电卤化、桑德迈尔溴化和铃木交叉偶联反应，对 4-硝基苯胺进行功能化，得到 26 种取代几何形状，其中 18 种结构目前无法通过现有技术获得。此外，我们证明该方法适用于多克规模的此类系统的批量生产。关于光电性能，我们展示了高度官能化的 HAB 如何表现出强烈的发光行为，这使得这些分子非常吸引有机电子设备。
